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My anal virginity

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By *mmacdxxx OP   TV/TS
over a year ago

Plymouth

Still an anal virgin. Not sure when that will change but here is a scenario I have fantasised about;

One weekday morning I was off work and feeling a bit horny. I decided to get out my black wig and my tiny black thong which I hadn’t done for a while. Dressing turns me on so much and as it had been a while I was so excited I wanted to cam and show off. I logged into skype and found nobody around. So I logged onto Fab and put a status up asking for cam fun and browsed the chat rooms. I love looking at big cocks and heavy cummers, but if I was to ever get fucked I’d have to start small. I received a few messages and cammed with a few people making them cum. I still hadn’t cum myself but I was wet with pre cum and throbbing. Then a little while later I receive a message from a guy in his mid twenties. He has a thin and smooth body which is what I like. He tells me that he has never been with a CD but has fantasised about it. I tell him I’ve sucked off a few guys but never been fucked. He seemed excited about the thought of an anal virgin. I told him that I could only start off with a quote small cock. He then sent me a picture of his cock, it was roughly 5 inches long but quite thin and smooth. It looked perfect for taking my virginity! I told him as much and explained that I get offers from all sorts of guys. Many with big gorgeous cocks telling me they’ll be gentle, I do laugh at these because as nice as they are I need to start off at my comfort. This guy and I continue to message and I find out his name is Dan and he calls me Emma. He sounds like a decent guy, non pushy and witty. We decide to cam and I have now popped on a mini skirt and some white stockings. Dan loves the look and his cute cock is hard. I ask him if he wants to fuck my tight hole and he does. I put my cam under my skirt and show him my hole. It has only ever had a finger in and he is turned on by the tiny tightness. Dan is rubbing his cock and I want him to cum for me. I begin to groan and call his name. This has the desired effect and within a minute or so he is stroking furiously and panting. I watch with excited anticipation for his climax. It arrives and his little cock erupts and shoots a sticky stream high up his body. His cock pulses more and a few more high jets burst out. As he writhes a few more little spurts come out. He is a decent cummer and his chest and belly are covered. Perfect cock and perfect cum. I then decide to cum and I let the cum run down my shaft and onto my hole. Dan loves it. We chat a bit more and I say he’d be perfect for my virginity. Dan agrees. The only issue is I am in Plymouth and he is in Bristol. I tell Dan that we should try and arrange something somehow and he is keen. We both have to go for a while but I said I would message him tonight. As we log off I know I have to make a plan and have Dan. All day I would think about Dan and what we could manage. I had an idea and I was ready to log on and suggest it to Dan, can we make it happen?

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By *avidking73Man
over a year ago

Barnet

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By *mmacdxxx OP   TV/TS
over a year ago

Plymouth

So that evening Dan and I were both online. We were chatting about our earlier cam session and both flirtily hunted that we would like the real thing together. I asked Dan if he would travel for a meet? He said yes depending on who and within reason. I said would he consider maybe an hour of travel? He said yes. I suggested that for fairness Exeter was between the two of us. I also said we could book a cheap hotel and meet there. Dan was interested and said he’d like to meet soon. I asked for some date ideas and we decided that we could make it happen very quickly. On a Friday evening in a few days time we both had the weekend off. Dan booked one night in a central hotel in Exeter. After work on the Friday we would both travel to Exeter and have a night together. Now I’m not the most convincing CD but I thought I’d try my best and take a wig and make up. Dan asked me to bring a skirt and a thong with stockings. This was fine. When Friday came I had a half day so I was able to get to Exeter first. This would be fine because I could then get ready and wait for Dan. So it was Friday morning, I packed my bag and put it away in the boot. I spoke to Dan and he was excited for the working day to be over. At work I was horny thinking about the night ahead. When I finished I drove to Exeter and went to the hotel. It was 2pm so I had plenty of time to get ready. Dan finished at 3:30 and would be here by 5. I had brought some booze to help me relax and as I sat on the hotel bed in man mode I knew I had to work hard to make myself semi passable. After a quick drink I started to get ready. My cock was hard at the thought of my first cock so I started by having a shower.

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By *dsindyTV/TS
over a year ago

East Lancashire

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By *ovaguy1Man
over a year ago

Chippenham

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By *kadMan
over a year ago

wallsend

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By *mmacdxxx OP   TV/TS
over a year ago

Plymouth

In the shower I used some lovely feminine smelling toiletries. I shaved the important areas and tried to be as smooth as possible. I felt relatively feminine and loved the clean fresh smell. I dried off and sat on the bed, naked and excited. In a few hours I knew I’d have a cock deep in my ass. I used some lovely moisturiser and some sweet perfume. By this time it was 3pm and I knew i had time to get myself as best as I could. I slipped on my thong and stockings. I then put a bra on. Over the top was a tight vest top and a mini skirt. Now I had to try and do the best make up job of my life. I used some foundation and then kept the eye area subtle. The main focal point was to be my lips so I used some slutty red lipstick snd completed my face. By now I was feeling more feminine than ever and there was one final piece to finish my look, the wig. It was black and long. I needed to give it a brush and then set it up on my head. I fixed it and tidied up to complete my transformation. Everything was set so I decided to look at myself in the mirror. I looked half decent! The red lips against the black hair worked perfectly. Now it was 4pm and in an hour Dan would be here. I sat down ready and had another drink to settle myself. Not long now!

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By *es for funMan
over a year ago

port talbot

good start well thought out so far keep it cumming mm

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

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By *ree guyMan
over a year ago

Fleetwood

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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 *mmacdxxx OP   TV/TS
over a year ago

Plymouth

I had a a little drink to settle myself and as 5pm approached I did feel a bit nervous but mixed with excitement. Dan messaged and I knew he was on his way. I received another message to say he had arrived but because he had been at work all day he wanted to shower before anything so he told me to leave the door slightly open and that he would go straight in to the bathroom. I was sat on the bed and I heard the door slowly open, footsteps entered and pushed the door closed behind before entering the bathroom. I heard the shower running and knew that anytime now things would be getting dirty. I could feel my cock straining in my thong as I thought about a wet naked man in the next room. I decided I couldn’t wait and I would sneakily have a look at him in the shower. I crept up to the door and slid it open slightly. I could see the back of Dan and he had a tight juicy ass. His body was bronzed and smooth. Dan was also tall. Watching the water glisten on his body was hot! I wanted to see more so slid the door more but it made a squeaky noise. Dan turned to face me and caught me perving on him. He smiled and told me to come over. As I made my way over I could see his cock was beginning to harden, he looked pleased with the effort I had made. As I stood in front of him his cock was almost level with my face due to him being stood in the bath and slightly taller. He then grabbed his cock with one hand and my head with the other. He pushed them together and I took his below average length in my mouth. It was easy to suck and I could deepthroat due to the smallness. I only sucked for a minute and Dan pulled back. His cock had red lip stick on and he said give him 5 minutes to finish in the shower and he’d be with me. He leaned over and kissed my red lips and his wet face ruined my Lippy and he was covered in lipstick on his cock and his face. I then left the bathroom and quickly sorted my make up before laying in the bed, awaiting Dan to continue where we had just started. The shower sound stopped, the room was silent as I eagerly anticipated the entrance of Dan. It felt like an age had passed as he dried off and got ready. But then I did hear the bathroom door slide open. Dan stepped out, his body was dry and looked so smooth and so clean. I looked at his cock and he was fully erect and the small thin penis looked like the perfect beginner tool for me. He approached the bed and this was it, now was the time for some sexy fun

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By *uke45Man
over a year ago

Derry

Great story x

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