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sissy meets an alpha man - Continued

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By (user no longer on site) OP     over a year ago

Over the next while the spit roast continued, the only difference was who was doing the roasting. When it came to my ass it was always one of the women with a strap on but my mouth was used by either the women or the men. Jane’s holes were used by all who wanted to and she seemed to be enjoying herself quite a bit based on the moans she was making. There was some jokes made about needing another maid to serve drinks while the maid and sissy were being roasted. The evening’s entertainment carried on for a good few hours with small breaks in-between. Alpha’s guests were impressed at how far I had come in my training and were looking forward to seeing other stages in the journey. Alpha smiled at them and then reminded me that at some stage it would be his cock that would be taking my ass, not just a strap on. I was not sure if my brain had got used to that idea totally but deep down knew it was inevitable that it would happen. It would take some more time and patience but I think I had always known it is what a sissy should accept. After this discussion the night ended and Jane and I were allowed to get dressed and leave. Understandably I was so tired and a bit sore when got home that I just collapsed.

Two days later I had a quick message from Alpha’s lady congratulating me on my performance and that I had done them both proud. Their four friends had really enjoyed the night and meeting me and all including Jane hoped there would be other such nights. I replied that I would be happy to attend and serve when they needed me to and was continually grateful for their patience. She went on to say that she would be around tomorrow evening for some more boot worship training as a treat for my night’s work. I was told to be ready in my cheerleader uniform.

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By *iverscuMan  over a year ago

Berkshire

Love this story.

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By *r 007Man  over a year ago

harrogate

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By *imale38Man  over a year ago

Barnsley

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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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By *iverscuMan  over a year ago

Berkshire

More please x

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By (user no longer on site) OP     over a year ago

The next evening I waited kneeling at my door, dressed as requested. She arrived dressed to the nines in a business suit with five inch heeled boots on. I crawled after her and when she sat down and acknowledged me I started to lick her boots. As I did she talked about all that had happened and the next big step, which was for me to take Alpha’s cock in my ass. They knew I was worried about it but felt the time was right and it was a step I needed to take. If I agreed they would set it up over the next couple of weeks and there would be an audience for my deflowering. This idea left me with mixed feelings of excitement and nerves but knew I wanted to do it. I kissed her boots and asked her to please set it up and I would do my best not to let them down. She patted my head and smiled at me and said “good decision sissy, you will love it” Before I could change my mind she messaged Alpha and told him they had the green light. My fate was set.

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By *ppetiteforsexMan  over a year ago

Isle of Man

[Removed by poster at 19/02/19 16:41:55]

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By *ppetiteforsexMan  over a year ago

Isle of Man

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By (user no longer on site)  over a year ago

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By *vanabeusedTV/TS  over a year ago

somewhere

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By *r 007Man  over a year ago

harrogate

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By *hocko87Man  over a year ago

dublin

Good story keep going

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By *iverscuMan  over a year ago

Berkshire

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By *atexpvcTV/TS  over a year ago

chester/Merseyside

Fantastic story please continue

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By *aidbacklookingMan  over a year ago

this town

Nice story line

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By *iverscuMan  over a year ago

Berkshire

We need more

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By *ylonLexiTV/TS  over a year ago

Blackpool

I agree, I'd love to read more xx

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By *exyPippa2405TV/TS  over a year ago

Alloa

I want to know more! Mmmmmm...x xx

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By *iverscuMan  over a year ago

Berkshire

Mooooore

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By (user no longer on site) OP     over a year ago

Two weeks later the night of my deflowering had arrived, all the training had been building up to this moment. Alpha and Lady decided to have another dinner party but this time just one other couple were invited and Jane was asked back to help serve. I was told to be at Lady’s by 3 pm so she could help prepare me for the night. I did not need to bring anything as they were providing all the clothing for the special evening. On time I knocked on the door and Lady let me, dressed in jeans and teeshirt and ankle boots – possibly the most casual I had ever seen her. She immediately led me to the bathroom and told me to completely strip off. When I had done so she removed my cage and told me to get into the shower. She tied my hands up and told me to bend over. She then put some lube in my ass and inserted an enema hose and let it fill me, This process was repeated four times until she was sure I was completely cleaned out, She then had me stand straight and she went over my body and got rid of any loose hairs that I had missed. I was then told to shower and dry myself off and meet her in the bedroom. When I met her there I found three outfits hanging up, one was a full French maid outfit with apron and head piece, one was a cheerleader outfit with socks and trainers and the third was hidden in a suit bag. I was told to sit on the end of the bed and my cage was reattached, I was then presented with white lingerie to put on, including stockings, suspenders, matching panties and bra, Lady then helped me into the maid uniform, tying the apron tight around my waist and placing the head piece on my sissy head, She then added a collar which was locked on, linked wrist cuffs and my five inch heels were kept on with linked cuffs. She then blindfolded me as she got ready as she wanted her outfit to be a surprise.

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By *hantelle-La-SlutTV/TS  over a year ago

South Birmingham

very nice

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By (user no longer on site)  over a year ago

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By *amantha_kelTV/TS  over a year ago

Magherafelt

This is great

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By *imale38Man  over a year ago

Barnsley

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By *vanabeusedTV/TS  over a year ago

somewhere

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By *r 007Man  over a year ago

harrogate

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By (user no longer on site) OP     over a year ago

Just before the guests were due to arrive the blindfold was removed and Lady was standing there in a full fishnet body stocking and black ankle boots. As always she looked stunning. She added a leash to my collar and led me into the kitchen where Jane was busy preparing things, dressed in her uniform of white blouse and black skirt. I was handed a tray of drinks and told to go stand by the door so the guests could help themselves as they arrived. First to come was Alpha dressed very smartly in a business suit. He whistled as he saw my outfit and then said “the big night has finally arrived sissy boy, your ass is mine”. Shortly after that the younger couple from the first dinner party arrived, took drinks and went to talk to Alpha and Lady. Then dinner was served, with Jane and I looking after them.

After they had finished desert, Alpha got up to speak. He outlined my history and our first meeting and the training that had led up to tonight. He then ordered me to walk over kneel in front of him and ask him something. Nervously I did as he directed and when knelt down, looked him straight in the eyes and said out loud “Alpha please remind me once and for all what a sissy I am and fuck my sissy ass with Your Alpha manly cock” The rest of the gathering, including Jane clapped when they heard this. I was then led on all fours to the living room where the bench had been placed in readiness. Jane helped Lady strip me down to my lingerie and my panties were removed. I was then bent over the bench and my wrist and ankle cuffs were linked in place so I could not move. Alpha then walked in front of me, having already taken his cock out of his trousers and he presented it to my mouth. I opened wide and took what I could in and started sucking it and making it wet. I knew this would hurt but was trying to reduce the pain a bit. As I was sucking him I felt hands on my ass as someone (I assumed Lady but did not know) started applying lube to my ass hole. Jane then knelt in front of me, took Alpha’s cock from my mouth and sucked it herself and then she added a condom. Without much more fanfare Alpha walked behind me, placed his cock at the tip of my asshole and asked if I was ready. Having been told earlier what to say I replied “Please fuck my sissy ass Alpha, make me a sissy for ever”. Not needing any more encouragement he gently started to push his cock into my virgin hole. As expected it hurt a bit and I could not help but shout out, but he ignored me and kept going. After some pushing and with help from the lube more and more of his cock went in until I could feel his balls slapping against my ass. I have never expected to be able to take his full cock but remembered the first time I had been taken with a big strap on and on easy that had gone in. Soon he placed his hands on my hips and started fucking me hard, shoving his cock in and out of my hole.

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By *urvy cathy2023TV/TS  over a year ago

rathmines

[Removed by poster at 26/03/19 10:45:17]

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By *urvy cathy2023TV/TS  over a year ago

rathmines

Fantastic story

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By *hantelle-La-SlutTV/TS  over a year ago

South Birmingham

Strap on are good but nothing feels like a nice cock.

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By *vanabeusedTV/TS  over a year ago

somewhere

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By *r 007Man  over a year ago

harrogate

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By (user no longer on site)  over a year ago

Still waiting for my first real cock

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By *llycplCouple  over a year ago

doncaster

Booked

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By (user no longer on site)  over a year ago

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By *r 007Man  over a year ago

harrogate

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By (user no longer on site)  over a year ago

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By *ellhungoneMan  over a year ago

Portsmouth

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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

Will this always remain a story?

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By *hannytragger99Man  over a year ago

london

Yes, now get writing!!!

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By (user no longer on site)  over a year ago

Wow wish it would happen to me

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By *r 007Man  over a year ago

harrogate

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By *exyPippa2405TV/TS  over a year ago

Alloa

Love this story....nothing better than developing your skills as a good Sissy Slut Whore! Mmmmm....more please. Love Pippa x

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