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sissy meets an alpha man
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By (user no longer on site) OP
over a year ago
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They had been chatting for quite a while now. The chats had started off normal and social but slowly he got me to reveal more and more about my persons thoughts and desires. Sometimes it is easier to talk about them online especially if don't think there is any chance of meeting in real life. Talking to strangers gives me a confidence to talk more openly and sometimes I forget how much I reveal.
At first it was just small things about growing up, discovering my interest in female clothes and my desire to please others. Initially this desire was to please and serve women and not in a sexual way. To be controlled, corrected even humiliated by them.
As the conversation flowed he got me to reveal more and more. About how some of my desires were changing and how I did not feel like most men, in fact I did not feel like a real man. How deep down I wanted a real man to recognise me as a sissy, even if was dressed in male clothes. To meet some one who could make me feel like a sissy from the get go. And he made me admit that I wanted to sexually please such a man, even if it did nothing sexual for me. He made me admit that a sissy's place was to please and serve alpha men and the pleasure for sissies was by pleasing. It did not matter if I got sexually turned on or not, my pleasure did not count.
Embarrassing as all this admission may be it was all okay. It was online with a stranger who I was never going to meet. He would not have the chance to make me feel this way in real life. Until the day he mentioned that he was working near by and wanted to meet for a coffee. If that was not bad enough he stressed that he expected me to be in sissy panties under my male clothes, not just the cotton ones I had admitted to wearing daily. He wanted me to wear the pink frilly knickers I had foolishly sent him a picture of. It was decision time, do I let my fear hold me back as often had or do I grab a chance and see. As it was just a coffee little could happen apart from me sitting opposite an alpha man who knew what I was and what I wanted. The wearing of the pink panties was the first stage in obeying him.
The day of the meet arrived and as I pulled the lacy pink panties up my legs I was still not believing I was doing this. I then zipped up the female jeans I often wore, making sure the panties did not show. After finishing dressing I headed out to the meet. |
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By (user no longer on site)
over a year ago
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More please hunny please , xxkaren |
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By (user no longer on site) OP
over a year ago
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It was just a coffee so I could but understand why I was so nervous. I had met dominant men before, had even scened with them in private or at clubs. So why did a coffee meet in public scare me so much. Maybe it is because of what we had talked about and how much he knew of the real me and my desires.
I reached the venue and got myself a drink and took a seat outside. I slowly drank as I looked around, imaging everyone there knew what I was wearing under my male clothes. I was also keeping an eye out for him though i only had a rough description. All of a sudden I heard "hello sissy" whispered in my ear, which made me jump. I looked around but there was no one there. I sat back down and heard "hello sissy" again, thus time convinced everyone heard it. I looked around and there he was sitting opposite me, having git himself a coffee between the two greetings. He looked totally like the alpha male, confident and assured. |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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Looking nervously over at the man sitting opposite me I struggled to know what to say. Finally I managed to squeak out an "hello and how are you". The man raised a smile as he understood how nervous I was in his presence. He replied that he was fine and asked if I was dressed as he had requested. Looking around me before I replied, I gently nodded in the affirmative. He looked straight at me and said "when I ask a question I expect a verbal answer, understand"? I looked at him nervously and said "yes I understand and yes I am dressed as requested". He smiled and said "much better". "Now drink up and we will go for a walk".
I did as directed and followed him out through the outside area and into the park itself. We took a walk around, trying to look like two friends having a chat. Making sure no one could hear us, he said "knowing you are wearing pink panties for me is making my dick hard and from what you have told me, I know your little clit is not reacting at all". I was sure everyone could see me go red with embarrassment as he said this. It is completely different being told this face to face rather than online in a chat. He went on to say that I was a naughty sissy getting him aroused and not been able to do anything about it. "If we were in private I would have you just in your panties and spank you for being so bad". There was little I could say to this so just said "sorry". |
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By *abbyLoveTV/TS
over a year ago
Bournemouth |
Great start to the story, keep it going. Think many crossdressers feel this way, always a big step that first step but can lead to some amazing things  |
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By (user no longer on site)
over a year ago
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Wonderful start. Do keep going!
I remember wearing my short red dress for my first meet. Parked in hotel car park, then walked through reception to the guys room. I only saw three of four people but I was so scared but also really excited too. That intoxicating feeling is quite addictive!
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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More! |
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By (user no longer on site) OP
over a year ago
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[Removed by poster at 04/01/19 14:48:17] |
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By (user no longer on site) OP
over a year ago
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As they walked along the man said to me "I have met many TVs/CDS and sissies in my time but not sure I have met one like you. For most the simple act of putting on something feminine, either for themselves or to please a man, would have their cock rock hard". "Of course their cocks come in different sizes and should of be locked in chastity cages with the keys held by their wife, partner or an alpha man". "But that is not the case with you and that is what intrigues me. You are out in public wearing sissy panties because I told you to which shows me that you like to please even if it does not arouse you".
I thought for a moment and replied "Even though it is embarrassing to admit I can't disagree with anything you just said. I am not sure I can explain it either. It's as if my brain shuts down my little cock when my sissy side comes out or the desire to please overcomes my own need for pleasure". "I have had a few meets with men when I have tried to please them orally, some successful, some not so". "I think in some cases there was a lack of dominance, a lack of knowing I was in the presence of an alpha man, who knew me better than I knew myself". After that semi public admission I was very quiet for the next bit of the walk. |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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We were both silent as we carried on walking until we reached his car. This is where we had planned to part ways until the next meet if there was one. As I was heading off he looked at me and said "get in the car sissy boy". I hesitated and he just looked as if to say "don't make me tell you again". The tone of his voice made me realise he was not messing so I opened the passenger door and sat in. He got in and locked the doors. He looked over and said "next time I give an order you just do it, is that understood sissy boy, I am the alpha and you have to trust me". I just nodded. He checked no one was around and told me to undo my jeans so he could see the pink panties. I undid my belt and the top so the ribbons attached to the panties lay over the top of my jeans. He looked at them, smiled and said "that's a good sissy boy". Hearing those words sent a shiver through me.
Again checking no one could see he told me to reach over and touch his cock through his trousers. "See what you are doing to me, you dirty little sissy boy. If we were not in public I would shove your mouth on my cock and make you suck it" I didn't know what to say but knew he meant it and was not sure if I would have been able to resist. He then said that the next meet would be at mine. "When I arrive, you will be kneeling at the door wearing just your pink panties and the pink collar you told me about. You will follow me into your living room on all fours and kneel at my feet". "You may feel like you should be in control in your own home but when an alpha male is around, a sissy is never in control". |
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Love it, very horny story, can't wait to read more xx |
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By (user no longer on site)
over a year ago
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Amazing x |
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By (user no longer on site) OP
over a year ago
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As he sat drinking his coffee with me kneeling, neither one of us said a word. He then looked at me and asked how I felt having an alpha man in my home, especially considering how I was dressed. I thought about it and honestly replied that I was not sure how I felt. It was a new experience for me and would take me sometime to totally take in. He smiled and said he appreciated my honesty. He asked for another coffee which I went off to get. On my return and after I put it down,he told me to undo his flies and take out his cock. "While I finish my coffee I want you to hold and feel my cock. It will give you a better understanding of why you are a sissy and why you are happy to please". Hesitating at first I did as requested and held his manly cock in my hand. I could immediately see it was bigger and thicker than mine and obviously could please women in a way I could not.
As I held it he could see a smile of recognition come over my face as maybe for the first time I recognised my proper place. He patted me on the head and quietly suggested that I kissed his cock. This would be a further step in my sissy journey, a simple gesture but a mind changing one. It was not the first cock I had touched but there was something different about it. It felt right to kiss this cock as if to admit that I knew it's owner was more of a man then I was. Slowly I knelt higher and gently placed my lips on the base of his cock and kissed. He smiled again and suggested I kiss his balls which I did. I then lent back as if to reflect what I had just done. The atmosphere felt different between us, as if our respective roles were now confirmed. He zipped up his flies and hit up to leave. I crawled out after him and thanked him for his visit and the lesson. "Continue to listen and take instructions well sissy" he said as he left. |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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Over the next few days there was some gentle teasing between us with his aim of constantly reminding me I was a sissy. The kissing of his cock had me thinking a lot about doing more than just kissing. I was not sure if I wanted to wank it or suck it, though both ideas scared me. I wondered if I was ready for that step and then realised it was not down to me. As the alpha he would decide when and what I did with his cock, it was his pleasure that counted after all. In a way I felt relieved in not having to make the decision and to just trust that he would know when the time was right. About a week after the first visit to mine he messaged to arrange another one, same rules as before. This time though he was bringing a friend. Nothing more was said.
On the arranged day I was on all fours by the door having buzzed him in. When the door was pushed open I did not look up as two people entered and went into the living room. I crawled in after them and when given permission I looked up. I was a wee bit shocked when I saw that his friend was a woman. He had talked about this before as a valuable lesson, to have a female see me in my sissy state and to compare our cocks. I just did not think he would do it so early on in our meetings. I was told to stand and put my hands on my head. His lady friend walked towards me and then walked around me, looking at every part of my body. She smiled at him and said that she could understand what he found so intriguing about me and that I was potentially a very good little sissy. She pinched my nipples and patted my bum. She giggled at my pink panties, stating that very few women would wear such panties. I remained silent during this description of me, not sure what to say.
He then stood up and told me to undo his flies and take out his cock and hold it in my hands. As I moved over to comply she followed and as I took his cock out she put her hand in my panties and felt mine. I knew I was not as big as him but felt I was at least average. She took my cock out and held it in her right hand. She then moved her left hand over mine and held his cock in it. It was as if she was comparing cocks just by her hands. |
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By (user no longer on site)
over a year ago
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By (user no longer on site) OP
over a year ago
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Standing there as she held both cocks in her hands was almost like a confirmation for me. Not having many close friends to talk to and not going around looking at other mens cocks I was not sure where I stood. And it was not as if I could ask female friends what they thought about it. This difference in size may have funded my sissy and cuckold dreams. Maybe I always knew deep down I could not please women with my thing so I needed other ways. I looked up at him as these thoughts went through my mind and just smiled. He grinned back as if he could read my mind.
She put my cock back in my panties and turned me to face him. With a gentle persuasion she pushed me to my knees. I would not say forced, more gentle encouragement to admit my place. As I fell to my knees I could not take my eyes off his cock which she was still holding. She bent down and whispered "kiss it sissy I know you want to". Don't know how she knew but she was correct so I bent forward and kissed it. They both smiled and then she said "now lick it sissy". I stuck out my tongue and licked the bottom and then ran my tongue all the way along the shaft. This gentle touch was greeted by a gasp from him and a "well done sissy" from her. For some reason both of these reactions brought a smile and contentment to me. |
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By (user no longer on site)
over a year ago
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[Removed by poster at 06/01/19 19:03:05] |
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By (user no longer on site) OP
over a year ago
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The two of them just stood there saying very little as I gently licked his cock. It's as if they knew that it was better to encourage and support rather than force. In time they realised I would find my natural place and maybe even think I got there all by myself. There I was kneeling in pink panties licking an alpha man's cock. It did not seem strange at all, maybe just surprised I took this long. I carried on licking with gentle pats on the head from her. She bent down and whispered "do you want to do more than lick it sissy"? I thought for a moment and nodded. She smiled back and said "then ask him nicely".
I looked up at him trying to think of the right thing to say. In the end I went with "can I please". He looked down and told me to try again, put a bit more thought into it. Giving it a few moments I finally thought what he may like to hear and said " may sissy suck your cock please Sir?". They both grinned and said that was a much better question to ask. He asked me if I was sure. Not wanting to back out of it I just nodded my head. He told me to open wide and take the top of his cock in my mouth and to watch my teeth. She placed her hands on the back of my head to guide me, again without force. It felt a bit strange having his cock in my mouth but did not try to remove it. With his occasional help I slowly moved my mouth up and down his cock, taking a bit more each time but trying not to gag. |
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By (user no longer on site)
over a year ago
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This is good  |
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By *r 007Man
over a year ago
harrogate |
would make a great video |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Just love this story ..so want to be the slut though |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Fantastic so far  |
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By (user no longer on site)
over a year ago
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Mmmmmm |
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By (user no longer on site) OP
over a year ago
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As I knelt there slowly sucking his cock I was trying not to overthink things. They often say that you shouldn't try your fantasies as reality rarely lived up to them. But this felt right, this felt natural. This felt like what I had been searching for. I still had an interest in women even if I knew deep down I could rarely please them sexually. I always held out hope that there were some women out there who wanted more from a man than what was between his legs and deep down knew there was. And while I had an interest in cock it was not just any cock. The man had to own a certain degree of dominance, control, assuredness in his ability but not too pushy or demanding. Someone who's presence was felt once he entered a room without having to say anything.
As these internal thoughts were going on they were just smiling as the training progressed. He looked down at me and said "I need you to take a bit more sissy but I will be gentle". She held my head as he pushed more of his cock into my mouth. I was having a bit of difficulty so he withdrew and then put it back in. Tears were coming to my eyes as he carried on trying to push more and more of his cock into my mouth. He seemed to know when to stop, just before I thought I was going to be sick. He withdrew until just the top of his cock was in my mouth and I could breathe normally. "Nice try sissy, well done and in time we will get past that gag reflex of yours". I just carried on sucking taking in what I could manage.
Something else dawned on all of us at that time. Throughout this whole episode nothing was happening to my own cock. It is as if my brain shut it down as if to remind me that my pleasure was in pleasing, not in sexual release. Maybe not for them but it was an eye opening moment for me. |
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By (user no longer on site)
over a year ago
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Mmmm |
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By (user no longer on site) OP
over a year ago
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Thanks for commenting and feedback. This is completely fantasy but possibly more honest than any of my stories on here. The feelings expressed is how I woykd expect to feel if such a meet happened |
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By (user no longer on site) OP
over a year ago
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[Removed by poster at 08/01/19 17:29:22] |
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By (user no longer on site) OP
over a year ago
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As I carried on sucking a small bit of precum dripped from his cock. She gathered it in her fingers and told me to stop sucking and purse my lips together. As if she was applying lipstick she rubbed the precum onto my lips, saying "take a taste of a real man sissy boy". It felt a but tangy, not that I was any great expert in what cum should taste like. He smiled as my slightly wet lips went back to sucking his cock. We had been engages in this activity for just under an hour and my knees and my mouth were a bit sore, but it was not my place to complain or call a halt. However they decided to call an end to the proceedings and tidied themselves up.
I stayed there on my knees until they were ready to leave and crawled out after them. At the door she thanked me for the entertainment and said she was curious to see how far my sissy journey would go. I replied that I was not sure if that was totally down to me, though my nerves and fears may get in the way. They both smiled at this and said that is where they came into the equation, to help me overcome those fears. As they left the alpha stated that next time would be at his and I would be tasting more cum, one way or another. I just nodded and said that I looked forward to hearing from him. When I was alone I had a lot to think about. |
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Great story. I’d love to be the sissy in the story. |
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That's a brilliant story,more please xx |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Fantastic story so hungry for more please... |
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By (user no longer on site)
over a year ago
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looking forward to the next part.. this captures very well the intense feelings of how good it feels when you let go and become one with your true sissy desires and needs.... but the hard part is to find such a confident and controlling, intelligent alpha male who knows how to deal with a sissy .... ... wow xx |
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By (user no longer on site) OP
over a year ago
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About a week later I was sent a message with his address and told to be there the following evening at 7. I was to wear my sissy panties under my clothes and bring the pink collar. As soon as I was let in i stripped to the panties and put the collar on. Untill further notice this was my sissy outfit in his or their presence. Directing me to get on all fours and follow he led me into the kitchen and showed me where the cups etc were and told me to make two coffees. He had left out a tray for me to serve them on. He then headed to the living room. As I was waiting for the kettle to boil she came in, stood behind me and tied a white apron around my waist. She showed me how to curtsey after I delivered the coffee and then went to join him. When the coffee was ready I took the tray in and placed it on a table between them. I then took hold of the apron in each hand and attempted a curtsey. This attempt made them giggle.
As they drank I was asked some personal questions about my sexual experiences, especially with women. It was slightly embarrassing to answer them but tried to be as honest as I could. I explained that I had not had many sexual partners and that it had been a long while since I had done anything sexual with a woman. And how this lack of experience had maybe conditioned my thoughts about sissies, chastity and the cuckolding lifestyle. And maybe even given me a fear tempered with respect for the alpha male. However my previous judgements had led me down wrong paths towards men who turned out to be bullies rather than alphas. I had come to realize there was a huge difference and while some men may want to use a sissy's holes, only a few could make a sissy comfortable enough to let it happen naturally.
They had kept quiet as I revealed very personal thoughts out loud and both thanked me for my honesty. He said that everyone was different and in the same way dominants or alpha men had reasons for how they were and what drives them, the same could be said for submissives or sissies. For some sissies it was an addiction to cock, for others the mental and control side were more important than the sex. It took time to really understand what drives someone but when that understanding is there wonderful things can happen. As we carried on talking she slipped off her shoes and asked me to massage her feet, which I gladly did. |
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By (user no longer on site)
over a year ago
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V good |
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By (user no longer on site) OP
over a year ago
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After rubbing her feet for a while I was told to stop. They both got up and left the room, telling me to follow on all fours. We ended up in the bedroom where I noticed a chair had been set up in the corner, facing the bed. I was told to crawl to it and kneel beside it. He looked at me and said that another part of the lessons was seeing what I could not do and seeing what it took to please a woman sexually. As he saying this she had gone to the bathroom and when she returned, she was now wearing a short robe and what looked like matching bra and panties under. Of course this was the first time I had seen her wearing so little and she did have a great body.
She approached the chair and asked me to take off the apron and sit down. As I did she picked up some ribbons and used them to tie my arms and legs to the chair so I could not move. She then returned to him and took off his shirt to reveal his bare chest. She then opened his flies and took out his cock. As they had taught me she got down on her knees and kissed the tip of his cock. She then started to suck it. Having more experience than me she was able to take more in without gagging. She looked over to me as she sucked his cock, making him sigh with pleasure. He looked over at me and said "look and learn sissy". |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Again having such an intelligent alfa male controlling the sub does mean a lot as the sub like. E want to be trained fully |
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By (user no longer on site)
over a year ago
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Alfa? |
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By (user no longer on site)
over a year ago
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Brilliant so far x |
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By (user no longer on site) OP
over a year ago
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To say it was strange being tied to a chair watching her suck his cock was an understatement. Watching porn had never really done anything for me, much preferred reading erotica than watching. I had often read stories about men in the situation I currently found myself, though most times they were married cucks and nut necessarily sissies. There was little else I could do but watch and admire her skill. As the first bit of precum dribbled from his cock she collected it on her fingers, walked over and rubbed it on my face. She then went back to his gorgeous cock which had grown with all the attention she had given it. If I had attempted to suck it now it would definitely have made me gag.
She stood up and removed her panties. He whispered something to her and she smiled as she walked towards me. She placed her panties on my head so the gusset was over my nose and mouth, but ensuring I could still see. Even though I don't have a great sense of smell I could get her scent and feel the wetness of her panties. She giggled as she said "that may be the nearest you get to my wetness sissy boy". As she went back to the bed she lay down in it. He stood up between her legs which she placed on his shoulders. Saying "this is how a real man does it sissy" his cock enters her pussy with one quick movement. He then starts to fuck her, starting gently but soon increasing the strokes until he is ramming in and out of her. Her head is back on the bed, eyes closed with gasps coming from her every time his cock hits her pussy. They carry on like this for about twenty minutes until suddenly she screams out as she orgasms. While she is in bliss he carries on for another ten minutes until he finally erupts in her. I am not sure if I have ever seen so much cum, a lot more than I regularly produce for sure. If another way was needed it helped drive home the difference between us. |
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By (user no longer on site)
over a year ago
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Alpha male wanting hot ts/t-girl convincing tvs |
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"Alpha male wanting hot ts/t-girl convincing tvs"
that doesn't make a sissy.
Love the story keep going.  |
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By (user no longer on site)
over a year ago
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"Alpha male wanting hot ts/t-girl convincing tvs
that doesn't make a sissy.
Love the story keep going. "
That booty just kept the story goin |
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By (user no longer on site) OP
over a year ago
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As I watched he took his cock out of her pussy, still dripping with cum. He walked towards me, removed her panties from my head and said "clean my cock sissy boy". When he said this he put his cock in my mouth and I could taste the mixture of their juices. I started to lick the cum from his cock, hence giving me my first proper taste of a real man's cum. He took my head in his hands and held it there as he fed me his cock. I was soon gagging and struggling to breathe as I tried to completely clean his cock. He finally withdrew and taking the last couple of drops he rubbed them on my face. "Any time you are in the presence of a real man and a woman, it will be your role to clean up sissy boy". That is the only use you have when it comes to sex, do you understand sissy"? I just nodded my head, too afraid to say anything.
After a few minutes he untied me and told me to kneel. When I did he used one of the ribbons to tie my hands behind my back. He told me to shuffle over and position myself at the side of the bed. When I was ready she moved down so my face was in between her legs, facing her pussy. Understandably this was the nearest I had been to a pussy in a long time and all I could do was stare. He then pushed my head down and told me to start licking. I gently put out my tongue and tentatively licked at the wetness in front of me. He slapped my ass and said "lick harder sissy, you are here to clean it all up". I increased my pace and soon my face was covered in the mixture of their fluids and I was swallowing a lot as well. My tongue was getting tired but there was no let up until they felt I had done a good enough job. He then positioned me back in the chair. Using her panties and a ribbon he gagged me so the cum had no where to but down my throat. He then went to join her on the bed, relaxing after their fucking and just looking at me. |
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This sounds like heaven. I'd love to be 8n your position one day |
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By (user no longer on site) OP
over a year ago
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As I sat there gagged with her panties and their combined juices I was not sure how I felt. It normally takes some time for me to digest and understand my feelings about certain activities. Often the first feeling can be simple joy for undertaking something for the first time as I can so easily over think and talk myself out of trying things. I appreciated that in this situation there was some control and encouragement on their part, but I would not call it force. I knew deep down that if I was not happy I could call a halt based on the initial discussions we had. I have often thought about finding myself in this situation but not sure if this panned out exactly as I imagined, which is often the case. While I respected them and their dominance/experience there was little emotional attachment to what had happened. Yes he was an alpha and I was a sissy but he was not necessarily my alpha and I was not necessarily his sissy. As for her there was little connection between us and if it had not been for him I would never have met her. I am not saying there is anything wrong in this but I guess when I had thought about it previously, I would be involved somehow with the woman. Either she would be my wife, partner or Domme and hence we would have a closer emotional connection which would have had a totally different baring on what I had just witnessed. I was grateful they had allowed me to watch such a personal moment between them and allow me to partake in a small way. I am not sure if it had the deep humiliation feelings I had always expected such a scene to have. Maybe my desire to please overcame any humiliation I may feel as my role and their behaviour was simply natural and what I expected to happen. I was eventually released, given the chance to clean up and dismissed for the night. As a reminder I was permitted to take home her panties and was told they would be in touch. |
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By (user no longer on site)
over a year ago
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This is a lovely story and as a sub sissy I can relate to the need to have an emotional connection too in order to feel true submissiveness |
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By (user no longer on site) OP
over a year ago
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A couple of days later I had a message from him asking if I was okay. I was honest enough to say I was still struggling a bit to understand all that had gone on and how I felt about it. I was beginning to wonder how different I was to most men. While witnessing what I did the other night most men would have had a raging hard on and would have been fighting the bonds. I just sat there as if it was a totally natural position for me to be in. Physically I was fine, it was my thoughts and feelings I was struggling to understand. He said that this was common and a better understanding would come in time. He asked if I had ever thought about wearing a chastity device. I replied that I had but was yet to find one that fitted my particular needs. Strangely he then asked if I had ever served food before and I told him that I had spent many years as a waiter. And shyly admitted this was where my love of waitress and maid uniforms came from. He asked me to be at his at 7 the following evening.
Arriving in time I knocked and was a bit surprised to be let in by her, as he had not mentioned she would be there. As was now normal at his I stripped to my panties and put the collar in. She told me to follow her. As we walked past the dining room I saw the table was set for two places. Expecting to be led to the kitchen instead I was taken to the bedroom. Hanging on the back of the door was a french maid uniform which she took down and handed to me. unlike most traditional french maid uniforms which are black, this one was pink with a white frilly apron. I put it on and she zipped it up and tied the apron around my waist. As a finishing touch she applied a small padlock to the top of the uniform, meaning I could not remove it. She explained that they were having a dinner date tonight and I would be serving the food. It was already cooked and being kept warm, I just had to serve the different courses and clear the tables between. At the end of the meal I would serve coffee and then wash the dishes as they relaxed. This was another step in the journey as sissies had to be useful in many ways to compensate for not being useful in a sexual way. While yet again taken by surprise by the turn of events I could see her logic. I then followed her into the kitchen where she showed me where the different courses were. She told me to wait there until she summoned me and not to forget to curtsey. |
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By (user no longer on site)
over a year ago
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Mmm |
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By (user no longer on site) OP
over a year ago
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About half an hour later he arrived home and was greeted by her. A few minutes later I heard a bell ring and nervously headed into the dining room. As I walked in the look on his face let me know he did not know anything about my new clothes. As instructed I dropped a curtsey and said "welcome Sir and Ms, I will be your waitress tonight". I then headed back to the kitchen, collected the starters and carefully walked back to the dining room. I placed one in front of her and the other I front of him, curtseyed again and retreated. From the kitchen I could just about hear him congratulating her on her improvements and on the surprise. Fifteen minutes later I was summoned to clear the dishes and deliver the main courses. This was all done in silence by me, ensuring I dropped a curtsey every time. After they finished the mains I was asked to deliver coffee. I was then told to swap aprons for a larger one and do the dishes as they enjoyed their coffee.
When everything was clean and put away to her satisfaction I was permitted to grab a quick bite and a drink. I then joined them in the dining room, having swapped aprons again and knelt at their feet. He complimented me on my look and on my service that evening. Been asked how I felt, I said "a bit strange, especially dressed as I was but was glad to be of service. The two of you are helping me learn more about myself and what I need". Continuing I said that I understood as a sissy my wants were not as important and often in pleasing others my wants would eventually be met. He smiled at this realisation and was happy they had helped me reach it on my own. "Many things can be read or told about sissies but often it has to individually learnt" he said. I just nodded. As I was done for the evening she unlocked my uniform, which I took off and hung up. I then dressed and left for to go home. |
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By (user no longer on site)
over a year ago
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Good as always |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Really well written story x |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
It is the realisation that you are here to serve others who appreciate having a TGirl for their own use... |
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By (user no longer on site) OP
over a year ago
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The few meetings I had with them had been an eye-opener and had reconfirmed some ideas in my head. Though I always wore female panties, they did not always make me feel like a sissy. I think it was just the natural choice for me. Only certain colours and materials made them sissy panties. And also on the occasions when I had dressed fully, including wig and makeup I did not feel sissy. At times there was a confidence that I was not sure where it came from when I was dressed, one I wished I had as male. The difference in personality was quite noticeable and some even took my femme side to be dominant. Nothing could be further from the truth but I was still learning. This recent journey was about what did it take to bring out my sissy side compared to my natural sub side. It definitely was determined partly by I was with and whether they could see a sissy whatever my clothing was. Part of the ongoing lesson was to feel more sissy at home alone.
A few days after the dinner I received a package from them. The note thay came with it had "practice makes perfect" written on the envelope. Inside the box was a rubber dildo, about 8 inches in length with realistic balls and a suction cup. The note inside read "sissies need to be able to suck without gagging and this takes practice. Every evening for 30 minutes dress in your panties, stick the dildo to the wall at the right level. Then get down on your knees and suck it. Start by licking the balls and then the tip. Then take what you can in your mouth". It went on to say that they had no way of knowing if I followed their instructions or not. I could say that I did when I had not bothered. It would depend on how serious I was about becoming a better sissy. If I lied I would only be lying to myself. I wondered how they knew me so well.
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By (user no longer on site)
over a year ago
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By *onmacMan
over a year ago
glasgow |
Its a fine story more please |
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By (user no longer on site) OP
over a year ago
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The following evening after work I came home, grabbed a bite to eat and then got changed into my sissy panties. I got the dildo from the drawer I had left it in and brought into my spare room. After kneeling on the floor to measure the proper placement of it I stuck it to the wall. I then walked over to the other side of the room and got down on all fours and crawled over to where the dildo was. I reached out with my tongue and licked the balls first and then licked the tip of the dildo. I then opened my mouth wide and took as much of the dildo in as I could, trying to remember what it had felt like to suck his cock. I ran my mouth up and down the length of the dildo, ensuring I was not gagging. This was all about practice and I knew it would take time for me to take more and more of the dildo in my mouth. Very soon the thirty minutes were up and I stopped sucking. It felt a bit strange kneeling in my own place sucking a plastic dildo but I was also glad I lived alone so had the chance to try it. There was a part of me that wished someone had been there watching my technique, giving me advice on how to do a better job. Leaving the dildo attached to the wall I retired for the night. Over the next few days I spent the required thirty minutes sucking the dildo, getting more and more into it and trying to take more in. Whenever I hit my gag reflex I stopped, not wanting to push too far or cause myself any damage. After a week I sent them a picture and a progress report. |
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Good girl x |
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By (user no longer on site) OP
over a year ago
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Due to life getting in the way it was a while before we could meet again, though we were in fairly constant contact. We had set up a kik group so the three of us could be involved. E very evening I spent thirty minutes sucking on the dildo getting more and more of it in my mouth. Hopefully the next time I was permitted to suck his cock my training would pay off. Then one day he arranged a meet at mine. He wanted me to greet him at the door wearing the panties and an outfit of my choice, something to show my sissy side to him. As per previous discussions he was not expecting wig or makeup. When he arrived I was wearing a cheap cheerleader outfit I had picked up from Ebay on a whim a while ago. My only experiences of cheerleaders were from watching sports online, the odd movie and some online erotica. When I opened the door he smiled as he approved of my outfit. Rather than taking me to the living room he asked me to crawl behind him to my bedroom, the first time he had been there. He asked me to get something to cover the bed and something for him to tie my hands. Intrigued by what he had planned I obeyed. When I handed him some tape he wrapped it around my hands and then had me lie on the bed, He then placed some tape over my eyes. He then undressed and got on the bed. “I know that you have cleaned my cock and tasted my cum sissy boy but another step in sissyness is a proper cum facial” I could not see but assumed he started wanking as I was lying there bound on the bed. He kept up the commentary about what a sissy I was and how different we were. After about fifteen minutes he erupted and I felt his hot manly cum land on my face. He had a decent load and it was going all over my face and lips. He cleaned himself up, undid my hands and got ready to leave, He told me to spend 15 minutes lying there covered in his cum and what it signified. I could then clean myself up and go practice on the dildo. He then left me to my thoughts.
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Mmm |
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By (user no longer on site) OP
over a year ago
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A few days later I had a message saying that she wanted to come around for a chat at mine. This would be the first time we had spoken without him, apart from when she dressed me in the maids uniform. She told me she would be there at seven and asked that I was wearing the pink panties and an apron but nothing else. When she arrived she was dressed in a professional business suit and white blouse, with four inch black court shoes on. I followed her into the living room and then went to make her a coffee. After I delivered it and curtseyed, she had me kneel at her feet. She started by saying how impressed she was with how i had taken to training so far. Many sissies may have the dream but not the desire or will power to follow it through.
She went on to say that there were three things she wanted to discuss with me and it may be slightly embarrassing for me to discuss them. But they both felt they were important topics in my journey and maybe easier to discuss with her alone. The first area she wanted to discuss was body hair. She understood that every sissy was different and hence they went to different degrees with regards to their body hair. Some removed it completely, others shaved now and then and used clothing to cover up. She had me stand and turn around so she could check mine. She even had me lower my panties so she could check there. In places I did not have much body hair but admitted I used to shave more than I currently do. She smiled and said as a minimum in future I was to shave my privates. Sissy boys like me should not have hair around their privates, only real men.
The next area for discussion was masturbation and how often I did it. This was definitely an embarrassing subject to disclosure, especially as I did not fully understand my desires or drive. I did not understand why reading about sissy use may arouse me but being used by a sissy did not. I said that my need for self pleasure varied a lot and I could go days without doing it or do it regularly. I had looked into chastity devices but had not found one that worked for me in both practical and financial terms. I needed one that was comfortable to wear long term and was also discrete. I mentioned how I had undergone periods of chastity by word, where a dominant lady simply told me I could not play with myself. It took a lot of mutual trust but my desire to please would kick in. Even if there was no way she could know if I played or not, the thought of cheating never occurred to me and if I did I would be bound to tell. She was a bit surprised at my willpower in this matter.
Thinking the embarrassment was done with for the evening she then asked about anal play. |
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By (user no longer on site)
over a year ago
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You got a very nice ass by the way |
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By (user no longer on site)
over a year ago
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More xx |
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By (user no longer on site) OP
over a year ago
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When she asked about anal play I got very quiet. It is a topic that had come up quite a lot down through the times on my sissy journey and I still was not sure how I felt about it. When you introduce yourself to many men as a sissy they expect you to bend over and let them fuck your ass. It was something I had read about and thought about, even imagined. But it was not something I felt ready to do yet. This could be due to old-fashioned beliefs, medical issues or just not met the right person. I explained all this to her quite shyly. I went on to say that I had experimented with things in my ass, like fingers, butt plugs etc. I even used to have a locking belt that kept my ass plugged.
She asked if a woman had ever taken my ass with a strap on and I nodded. I related the tale of visiting my first pro Domme while I was in holidays, asking her to make me feel like a slut. I was dressed in matching red lingerie under my clothes teamed with stockings. After some verbal teasing she had me on all fours and lubed my then virgin asshole.i don't remember the length of the strap on but it was long and she was surprised as to how easily it slipped in to my waiting hole. It felt great as she fucked my ass. It was something I got to experience a few times since but not many. One of my concerns was some suspected damage back there but no idea how it was caused. I used to fantasise about being made to cum as I was being fucked with a strap on, or being spit roasted, real cock in mouth and strap on in ass. There was also a strange fear that if I let a man fuck my ass I may like it too much.
I then went very quiet after these revelations. |
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By (user no longer on site) OP
over a year ago
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She smiled at me and thanked me for my honesty and for answering her questions. It gave her things to think about and would be in touch soon. On our next meeting she mentioned introducing me to enemas and back into anal play.
She then left. |
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By (user no longer on site)
over a year ago
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Go on... |
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By *r 007Man
over a year ago
harrogate |
enemas mmmmmmmmmmmmmmmmm |
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By (user no longer on site) OP
over a year ago
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About a week later she rang me and told me to expect her at mine at 6pm the following evening. When she arrived she was carrying a bag of supplies with her. Expecting her to go to the living room, I was surprised when she headed straight to the bathroom. She started setting up an enema kit, which I had seen before. Over the years I had them for medical reasons and once it twice for play reasons. She told me to strip and get on all fours in the bath. After putting on some rubber gloves she applied some lube to her fingers and rubbed it around my ass hole. After applying some more she pushed one then two fingers into my hole. They felt tight as it had been a while since anything had been up there. Unexpectedly she reached around with her other hand and started wanking my little cock. She explained that I needed to associate sexual pleasure with having my ass full, even if I did not have a great sex drive. She then stopped, lubed up the enema nozzle and inserted it deep into my hole. Once she turned it on I was soon being filled with water and it was rather uncomfortable.
Once my bowels were full she left me like that for fifteen minutes and then finally let me empty. She repeated the whole procedure two more times until I was completely cleaned out. She then lubed up a butt plug and pushed it into my clean hole, filling it. I was then told to get out and stand in front of her with my hands on head. As I did I felt her reach between my legs and pull something up and around my waist. She had remembered what I had said about the locking belt. The back strap pushed against the base of the plug, keeping it in place. The strap came through my legs where there was a cock ring and then up to join the belt around my waist. She quickly locked it in place and now the plug was going nowhere. It was going to take me some time to get used to wearing and walking with a plugged ass. She explained that she was leaving a key so I could go to the toilet but the plug went straight back in after. She would randomly ask for photographic proof it was in. |
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Mmmm my cock just got very hard but was restric5ed in my cage  |
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By (user no longer on site) OP
over a year ago
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Over the next couple of weeks I had little contact with them as life got in the way. I wore the belted plug each day and still spent thirty minutes each evening sucking and licking the dildo. I think my technique had improved but it would be their opinion that counted.
She got in touch one day and invited herself around to mine the following evening. I met her at the door dressed in the cheerleader outfit with the belt on under. She wore a black skirt, blouse and boots. After serving her a coffee and taking my place at her feet, she enquired as to how my dildo and anal training was going. I replied that I thought both were going well but the belt still took some getting used to. She had me bend on all fours so she could undo it and check for herself. When she removed the plug I felt empty. She reached into her bag and took out a bigger plug, stating she would insert it before she left. She told me to stay in position as she excused herself for a few minutes to visit the bathroom.
As I saw her boots come back into view I looked up and was greeted by the sight of a large strap on sticking out from her waist. She had removed her skirt and blouse and was now just wearing the boots and her lingerie. She beckoned me forward and said "suck my cock sissy, let's see if your training is paying off". Imagining it was the dildo on the walk I licked the tip of the cock and then took it in my mouth. I think she was impressed with how much I got in without gagging. I started to suck it up and down as she patted my head and said what a good sissy boy I was. She told me to get the strap on nice and wet to prepare it for my other hole.
After about twenty minutes of sucking she told me to turn around and brace myself. She took up sone lube and applied it to my asshole. She then placed her hands on my waist, lined up the cock and shoved it into my hole. Even though it was still a bit tight ,the plug training had paid off and it slipped in rather easy. She started off gentle but soon increased the tempo and started fucking my hole hard. As she had done before she reached around and started to wank my cock. This feeling of being filled while being wanked was something I would get used to. She stopped wanking me and concentrated on fucking my hole. She mentioned that soon I would be ready to be spit roasted. She carried on fucking me for forty minutes and then withdrew. Before I could get used to an empty hole she put the new plug in and locked the belt in place. I stayed on all fours as she went to the bathroom to clean herself up and get redressed.
On her return she told me that I had done a good job and she would look forward to fucking my hole again. Knowing how much I liked to do it as a reward she let me spend fifteen minutes licking and worshipping her boots before she left. |
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By (user no longer on site)
over a year ago
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Amazing x |
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By (user no longer on site)
over a year ago
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You have captured how I feel when I am dresses so wonderfully x |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Are there such types out there that woukd be looking for a sissy to develop just like this..if so it is something I woukd consider.genuienly.. |
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By (user no longer on site)
over a year ago
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Mmmmm sexy |
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By (user no longer on site) OP
over a year ago
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"Hot story "
Glad you are enjoying Goddess |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
I think your are spot on with your comments on what your thinking about a d what goes through your mind on meetings... |
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By (user no longer on site) OP
over a year ago
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Over the next couple of weeks I carried on with the dildo sucking, wearing the plug and even teaching myself to self enema. She popped around a couple of times with her strap on to continue to train my ass. I was not sure if she was preparing me for the real thing there, something I had dreamt about but never had the nerve to try. I was then summoned back to his place on a Friday evening. I was told to clean myself out the night before and to bring the cheerleader outfit. When I arrived it was only her there. She let me get changed and then led me to the second bedroom, in which rested a bench. I was led to it and strapped in place. She then removed the belt and withdrew the plug from my ass. Leaving me alone for a few minutes she came back in wearing her strap on. She walked around the front of me and placed it in my mouth and said "suck it". I did as directed, taking as much in as I could without gagging. After a few minutes she pulled out, walked around to the back and entered my hole. While she was fucking me I wondered where he was.
Just at that moment the door opened and on he walked. He looked at the sight in front of him and said to her "so this is the surprise you were talking about. I like it very much." She smiled at him and explained that she was getting me ready for him but that would not happen tonight. She carried on to say that she had left one hole free for him. He grinned as he undressed and walking around the front he placed his cock in my mouth. "Time to see if your training is paying off sissy boy". I licked the top and started to suck it like I did the dildo. My gagging was better as I could take more in. Soon they built up a nice rhythm, shoving their cocks in and out of their holes. As I lay there being spit roasted I wondered if I had found my true calling. |
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mmmm can i swap places with you .
I have been spitroasted like that and loved every second of it.
And yes you found your true calling. |
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By (user no longer on site)
over a year ago
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Wow |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Mmm spitroasting sounds just devine but i guess it would need to be planned ahead for this to happen..very curious |
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By *etasubTV/TS
over a year ago
West London |
Just love being spit roasted |
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By (user no longer on site)
over a year ago
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Love this when with a couple.
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By (user no longer on site) OP
over a year ago
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They kept the spit roast going for about 30 minutes, her fucking my ass and him fucking my face. With a shout he erupted and his hot manly cum filled my mouth and throat. There seemed to be an endless supply. Eventually they both withdrew and my holes were empty. She quickly filled my asshole with the plug and locked the belt back in place. They left me strapped down as they cleaned themselves up. I was then released and given some water to drink. He congratulated me on my oral training and on how much my gagging reflex had improved. Strange as it may seem having him say that sent a small shiver down my back. While I continued to drink they discussed the journey so far and what was to come.
They enjoyed the spit roast but asked how I would feel if they were at opposite ends. I explained that I figured that is where they wanted me to get to but the idea scared me. I had often thought about it but never sure if was ready for it. However their natural dominance and their ability to put me at ease in my sissy state did help. It was something I would definitely consider but would need a bit more time and their continued guidance and assistance. This they agreed to readily and I was dismissed for the evening. |
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By (user no longer on site)
over a year ago
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Admiration any1 else into this wer stright guys travel around bein admired naked showing off wankin while other watch n admire luv it me so do my admirers haha  |
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By (user no longer on site)
over a year ago
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Still great story x |
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I love the story, very erotic and stimulating, keep up the good work. |
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By *atexpvcTV/TS
over a year ago
chester/Merseyside |
Don't stop I just love this story it all about giving control to others not just the dressing .I love it so much |
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By (user no longer on site) OP
over a year ago
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[Removed by poster at 02/02/19 11:37:03] |
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By (user no longer on site) OP
over a year ago
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About a week later I had a message that I was expected at a local pizza restaurant the following night at seven. I was to dress smart but wearing the plug and pink panties. They would be there but I was not to sit with them or interact in any way unless they initiated it. Curious and nervous as to what they had planned, after work the next day I showered and over the plug and panties I put on smart trousers and a white shirt. When I got to the restaurant they were already there but I ignored them as instructed.
I was seated the other side of the room from them and could see them looking over every now and then. He was dressed in a business suit and she wore an evening dress and heels. They looked like a couple out on a date and I was not sure what I was doing there. I ordered and enjoyed my meal, well used to dining alone. I was curious as to what they may be saying. I then saw the waitress approach them with their bill. He pointed to me and had a quick word the waitress. She looked over at me, smiled and then walked in my direction.
As she approached me she quietly said "The gentleman said that you would be picking up their bill, is that correct sissy?". It took me a few seconds to realise what exactly she had called me and when I did I was glad she had whispered it. Perhaps I should have been mad that they involved a perfect stranger in our games but I guess they were been as discrete as possible. They or the waitress could have made a bigger fuss about it. I just nodded and handed her my card to cover both bills. They smiled at me as they left and I stayed a few more minutes to compose myself. As I left the waitress in question threw a smile my way. Throughout the whole episode not a word passed between me and them. |
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By (user no longer on site) OP
over a year ago
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On my way home I got a message from her thanking me for the meal and congratulating me on not over reacting. They knew that I was not into public humiliation but felt this would be ok. She explained that the waitress was a friend and they knew she would be discrete enough. I just had to trust them to know how far they could take me. She also said that there was another reason they wanted me to meet the waitress. They were soon throwing a dinner party for some friends and Jane (the waitress) was serving at it. They thought that she could do with some assistance and immediately thought of me. They would provide a matching uniform and I had the choice as to whether or not I wore a hood. They choose their guests well and know they can be discrete. After a few minutes to think I agreed and said I would think about the hood. |
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By (user no longer on site) OP
over a year ago
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About a week later it was time for the dinner at his place. I was informed that there would be two other couples there and Jane and I were to be serving. I was told to arrive at his at six to get ready and to ensure I was clean in and out, with the plug in place. When I got there I was shown into the bedroom where an outfit was laid out on the bed. It consisted of white lingerie including stocking, a black short skirt, white blouse and black heels. Beside it there was a collar and a white apron. I had decided that I would be brave and forgo the hood. I got dressed and went to meet Jane in the kitchen, who was dressed the same apart from the collar. She handed me a tray with some drinks on it and told me to stand near the door and offer everyone one as they entered. When I headed into the main room Alpha and his lady were the only people present. They complimented me on my look and my decision not to wear the hood. Just then the door bell rang and I moved towards the door with my drinks tray. A middle aged couple entered and after Jane took their coats I offered them a drink. They took one without even giving me a second glance. About fifteen minutes later the last couple arrived, who were a younger couple. They were offered drinks, again ignoring me as I was just the help. After a while Jane said that the food was ready and they took their seats at the table. I went to the kitchen and helped Jane serve the starters and then stood by in case anyone needed any more drinks. When not in use I stood with my back to the wall, hands held behind my back, keeping very quiet.
The evening went on without much trouble, with Jane and I serving the different courses and keeping the drinks topped up, I could not hear much of the conversation but it seemed as if the three couples knew each other quite well and were used to little gatherings like this. I could not tell if they were used to be served by a sissy maid but it did not seem to bother them much. At the end of the meal we cleared away and I was set the task of filling the dishwasher and putting things away when they were clean. During this tine Jane had disappeared into the main room and was not sure what was going on. After I was finished I was summoned to the main room where I saw that the evening had taken a more relaxed turn. Jane was bent over the couch in just her lingerie while Alpha was fucking her cunt and one of the other men was fucking her mouth. I was told to strip down to my lingerie and take the same position behind her. Once ready Lady came up behind me and undid the belt and withdrew the plug from my ass, which was accompanied by a gasp from the other two women. The younger women approached my front and I noticed that she had put on a strap on which was soon positioned at my mouth. Remembering my lessons I licked the tip and took what I could into my mouth without gagging. As this was happening I felt Lady lube my ass and soon that was filled with her strap on. So there was Jane and I both being spit roasted on the couch side by side as if it was perfectly normal.
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By (user no longer on site)
over a year ago
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By (user no longer on site)
over a year ago
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Luv bein admired naked while playing admiration |
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By (user no longer on site) OP
over a year ago
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Started new thread for those interested |
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