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One time with a friend and her bf
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So I've never actually shared this story with anyone other than an ex. When I was 24 (so about 9 years ago) I had a really good friend that I worked with. We got on great and I trusted her enough to tell her I dressed occasionally. She was curious about it all but not into it so to speak. She even offered me clothes she didn't want anymore but she was a couple of sizes smaller. One day we were at work and she asked to see a pic of me dressed. I dudnt think much of it so told her I'd dress later and send some pics. I did and she replied with a thank you and nothing else. I was a bit confused and about a week later she admitted it was for her bf that she'd told about me. She was worried I'd be annoyed she'd told him but I know if you tell someone then there's a chance it will be told to their partner but I trusted her not to tell anyone else which she didn't. So I asked what they thought of the pictures and that's when she said that they'd love to see me dressed in person and if I fancied coming over with some clothes one evening...
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Continued...
So one day I took a bag of stuff in my boot of my car and drove to hers after. We got to hers and started getting changed. She even did some makeup on me. I'd only ever worn lipstick before and makeup didn't bother me but she applied some foundation, eye shadow, mascara and lip stick. We heard the door downstairs shut and as she went downstairs I finished putting my holdups and shoes on. As she asked I shouted downstairs that I was ready. First she walked in then he did. In that moment I felt so exposed but so aroused. We had spoken that he may want to go down on me and to my surprise almost instantly his hand went up my dress and I felt his hand touch me. It wasn't long until he was on his knees lifting my dress up and sucking me. He had apparently been into trans recently but this was his first time doing anything with a cock. He was ok, nothing amazing but I got hard no problem although part of that may have been due to my friend watching. After a little while she got him to take his clothes off. He was rock hard and I asked if he minded me reciprocating. I got on my knees and about 3 muns later he had finished, mostly on my face, a bit in my mouth. He the started wanking me a bit and then instructed my friend to suck me. She duly obliged and took me in her mouth. A few mins later she was bent over his lap taking me raw (none of had been prepared this would happen). Just as I was about to cum I pulled out and he swallowed every drop! |
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Thabk you all for replies. It wasn't the last time we played...
Obviously I saw her most days in the office and one day we had a quiz after work at a local golf club. We often shared lifts and she had given me a lot in the past as I was a newer driver so I was making up for it and driving her to most things. We were on the same team and sat next to each other and twice she put her hand on my leg. When we got back to the car she told me she hadn't stopped thinking about what had happened a fee weeks prior and wanted me to join them again. We started going through different scenarios/combinations we could do as a three and when we got back to the work car park where her car was I was visibly aroused. She undone my trousers and started going down on me. We then swapped and she positioned herself sideways on the seat, dress lifted and I went down on her until she came then she got out of the car and bent over the seat. Again we had no condoms so it was all raw. We fucked for about 20 mins undisturbed until I had to explode. She crouched down and opened her mouth allowing me to cum (mostly in mouth, some on face). She simply said we will definitely invite you over some time and got in her car and drove home. About an hour later she texted me to ask what I was doing that Saturday |
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Obviously I made it clear I was free on Saturday and agreed to go round. I turned up at 5pm. It was just her with him being at football. This gave is time to get ready. I'd brought a bag of clothes as requested and tried on a few things. We settled on a red dress as she had a similar one, a red pair of high heels, stockings and red underwear. She got dressed up too. She then started sucking me and sent him a pic to let him know we were ready. Luckily hw wasn't far away and came straight upstairs to find me going down on her, both still fully dressed and her dress lifted up. She told him to get naked as I went down on her she went down on him. Wasn't long until she came and was asking to be fucked. I of course obliged and we spitroasted her. She had told me after our midweek escapade that she had wanted to try anal and had started using toys etc so in this position I started rubbing her ass and using her own wetness from her pussy started fingering her ass. She came again and was constantly screaming/moaning. She then told him to sit down and told him to watch her get properly fucked. This had turned into a bit of a cucking bit I was all for it. She took her dress off finally, sucked me a bit more then bent over the bed. We fucked like crazy - hair pulling, spanking, choking, all the normal stuff. He just watched. I had to admit a couple of times I was struggling not to cum and eventually she told me she needed to stop too and told her bf to cum over. She sucked him a little bit and then pushed me right on him and told her bf to use his new sluts mouth. As he face fucked me she bent down and sucked me. I was the first to cum, her swallowing my load, choking slightly. I looked up at him and I knew he was ready. He pulled out of my mouth and came over my face. She kissed me, then him. I got showered and changed and we sat and chatted about shit. Work, football all that as if nothing had just happened! About 2 hours later I left with the biggest smile on my face. After this me and her did something most weeks and the three of us would meet every couple of months or so. Each meet was similar, a cucking aspect on him but also me being something of pleasure for them both to use. It was incredibly hot. It wasn't long before they got engaged and I was invited to the hen do...as the only male...(yes this is a true story - and no im not showing pics of them but can answer any questions to verify the truth somewhat)
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So the hen do! Can feel some excited anticipation for this on! Hopefully it lives up to expectations. So the hen do starts with us all heading into London and doing burlesque... yes I have videos of me doing burlesque with a group of women and I loved every second of it. I was in full male clothes but admired the females dancing around as I attempted my best moves. Following that we split into 3 teams and did a treasure hunt thing like get a stranger to propose, get a guy to flash their chest etc. The real fun definitely started back at the house. During some pin the dick on the groom there was some excitement and one of the girls lifted my friend (the hens) top up and one of the girls was like woah Scott (not my real name) will see and my friend was just like dont worry he's seen it all before. Nothing was made of it until later on that night when me, my friend, her maid of honor, the maid of honors hot sis and the hot sisters equally hot friend were just sat on the sofas. The maid of honor brought up the comment and the hen basically admitted to me and her having sex and then when timings were questioned had to admit her husband to be was fully aware and it started with all of us. It then got on why it started and how I would dress up and he was into that and then it escalated into more mid term thing. Obviously the girls being girls were willing/keen to see me dressed so we all went upstairs and the maid of honor and her sis got some clothes. They were of very different body shapes to each other and to me but eventually we found a dress, some lingerie and tights that fit. Sadly no heels. There I stood in front of 4 girls dressed up, clearly erect... |
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Continued... my friend, the hen was stood directly in front and as I was looking at her in her pink pvc dress I felt a hand go up my dress and feel the exterior of the the underwear I had put on, it was the maid of honours hot sis. She asked the hen if she really fucked me and she said yes and they literally started talking about our sex whilst she just lightly stroked me under the dress. She then without hesitation got on her knees and pulled my thong off and started sucking me. After a few mins she turned to the hen and said he's ready for you now. She grabbed my hand and we started to go upstairs when the girl who had just been sucking me stopped her and said "no, here...in front of us" |
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So she bent over the sofa, I went down on her a bit and aa I did the maid of honour started stroking me a bit and asked the hen if she was ready as I was. She said yes and she basically put me in her. I started fucking her and the maid of honours sister started kissing me all of a sudden, then her friend did. I was surrounded by 3 other horny girls whilst fucking my friend. Whilst kissing them I started reaching between their legs and could feel through their underwear how wet they were. I told my friend to get on top of me and I laid on the floor, as she grinded on me I asked them who wanted to sit on my face. A slight hesitation before the maid of honour said she would. Within a few minutes she had cum. Her sister then replaced her and a similar result ensued. The hen then got up and admitted her legs were gone so she couldn't ride any more but I said I still had one girl to make cum from sitting on my face and thats when the maid of honours sister who I'd just made cum grabbed my cock and asked if she minded her taking over. The hen looked at me and was like yes! She started riding me whilst her friend grinded on my face, I was having to try hard not to cum now but managed to make her friend cum. My friend then told me to fuck the maids sister how I sometimes fuck her. I bent her over, grabbed her hair in my hand and leant her back on me and went for it. The screams were incredibly hot and led me to uncontrollably exploding, slightly inside her as I tried to pull out in time but mostly on her ass. She turned around and got on her knees and straight away cleaned me up. As she did this my friend kissed me whilst the girl I had just fuckeds sister I think had just realised she had just seen her own sister get fucked and wasn't quite sure what to make of it lol. I won't lie, after getting dressed upstairs and coming back down it was very awkward. Me and the hen, stood outside and said bye with another kiss and I left them to it. Apparently the next day when they woke up there was a significant argument between the two sisters about what had happened but everything was fine by the time I saw them again at the wedding thankfully!
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