Fact
18 Oct 2018


As a young man in the army I was once on a short course in Pretoria. While on this course, I stayed in a hotel in the CBD. Every night was a night of drinking and pub crawling with friends. This one Thursday night while out with friends to one of the clubs in town for a ladies night thing we hooked up with three beautiful ladies. One of this ladies, Jenny was her name. She was stunning, long beautiful blonde hair, legs so long, fit sexy and smooth. Her boobs were magnificent, just watching them juggling while she danced made me weak. Now seeing that I was the one who got the ladies to come sit at our table in the first place and paid for their first drinks, my two friends had courtesy to allow me the opportunity to be the first one to make a move on these ladies and choose the one I liked. Needless to say, I choose Jenny. I started by asking her for a dance which she gladly accepted.

During our dance she allowed me to fondle her breast and touch her ass but never allowed me to pull her against me. By just having her so close to me and in my arms I was really getting turned on and was sporting a hardon in no time. We went back to our chairs and sat next to each other. Through out the entire night she played with my cock under the table through my trousers but refused all my attempts to play with her pussy, she didn't have any problem with me fondling her boobs, even in full view of others. This was strange, but it was nice so the night continued. Some of the guys (I suspect they are the regulars at this club) looked funny at me. One of them even asked me in the bathroom if I liked Jenny and that I don't have a problem with her. Naturally my answer was yes I liked her and I don't have any problem with her, he seemed surprised so I just left him and dismissed it as one of the guys who thinks every beautiful girl in the club is a whore. Some time around 1am we left the club for my hotel room, on arrival we sat on a couch and played a little, we kissed and fondled she looked funny at me. We drank some beer and continued having some fun. I got up and went to the bathroom for a leak and came back.

I past by the fridge and got more beer for us. When I sat down she asked if she could use the bathroom and I said sure carry on. She went and came back where we sat and resumed our kissing and fondling each other. What was strange was that she still refused to let me touch her pussy which I didn't mind very much. On completion of the two beers we had, I asked her if she will be spending the night or should I drop her somewhere. Her reply was that she would not be there with me if she didn't want to spend the night. I said that's cool and took her by the hand and led her to the bed. I said she must get herself comfortable while I use the bathroom for the last time before I go to bed. When I got in the bathroom I could already see that something was not right, yes something was definitely wrong, the toilet seat was up and I left it down the last time I used the toilet. This didn't make any sense, why did she put up the sit when she used the toilet. I needed to think and think fast. I thought about the funny looks I got at the club, I asked myself, does she have a penis, is it why the other guy asked if I'm OK with her?? I didn't have answers for this except that maybe she does have a penis, and the biggest question was what do I do now. Do I confront her about the toilet seat and the fact that she has been refusing me access to her pussy the whole night? I finished my business and went back in the room, the light was switched off. I just switched it back on and got naked. She complimented my cock and I got under the covers. She was laying down facing away from me. I laid down and spooned with her pressing against her. My cock was very hard pressed against her ass. She was naked except for her panties. I played with her boobs pulling a little on her huge nipples. She reached back for my cock and started stroking slowly. I tried again to reach for her pussy but she changed position making sure I don't get to feel her up between the thighs. She turned and went down on me. Jenny is a good cock sucker, she started with the tip and then she licked the underside of my cock before she sucked it all in her month deep throating me. All this time when she was sucking me I held her blond hair and urged her on. She continued sucking alternating between my cock and balls and occasionally licking and sticking her tongue in my ass, that was a wonderful feeling which actually appeared to be nothing compared to when she would suck me and stick one of her fingers in my ass, I never had anyone playing with my ass before and I could swear if she didn't stop I was going to cum right there.

She paused and stood up, taking off her panties in the process. She went on all fours and indicated for me to take her doggy style. I lined myself up behind her with my cock in hand but she took control of my cock and guided me to her back door, when I realized that she wanted me to fuck her ass I just told myself I'm not gonna ask questions. She controlled the entry and it was done very slowly until I was half way in then she started a slow rhythm back and forth until I was buried deep inside her. I started pumping and I reached around to play with her tits. She started going crazy encouraging me to fuck her ass. I reached for her pussy but found her hand there, she took hold of my hand and guided me down where I was shocked to touch a full erect cock. I stopped pumping immediately and she looked back at me and said relax baby just enjoy the moment. I felt disgusted but my cock had a different idea, I could feel myself getting even harder in her ass. And my hand started jacking her slowly while I resumed fucking her ass. I didn't last very long and I came like I never did before and collapsed down on her.

My cock deflated and I withdrew from her and laid down next to her without saying any word. She started by apologizing saying that she was not sure how to tell me and she didn't want to let go off me. I said that I'm still shocked and don't believe what just happened. She asked if I never had anal sex before with a woman to which I answered no. She asked if I would willingly have anal sex with a woman and I said yes, then she said ok just continue thinking of me as a woman because that's what I want to be to you and we can have anal sex. I said cool but I'm still not sure about all this.

We started kissing again and and I was instantly hard, without thinking my hand just went down and I felt her cock in my hand.

This was my first ever cock that I have touched, it felt strange, and yet so interesting, in the beginning I thought that I was going to freak out, but it turned out that i actually enjoyed playing with this cock now fully in my hand with my jacking movements no longer on a slow side of things. I continued to jack her cock, she grabbed mine and jacked me up and down too. We were both rock hard in no time. We changed positions and we laid side by side facing opposite directions. I felt her hand being replaced by her mouth on my dick and I didn't wait for an invitation. I followed suit, we were laying there side by side with a dick in mouth for each of us. I never touched a different cock except for my own one, and now here i was sucking on one like my life depended on it. I sucked that cock and I sucked it good. She went for my back door with her tongue and occasionally putting one finger in there, I was in a different space, nothing mattered anymore, i was enjoying the moment. i felt the second finger entering my ass, and by now I knew exactly where this was going. I had to make a choice even though I knew that the choice has been made already. With the two fingers in my ass and her mouth around my cock I knew i wasn't going to last long. I announced to her that if she didn't stop I'm going to cum. She pulled her fingers out of my ass and asked me what I wanted her to do, I knew the answer, but I was speechless. She pushed her arm underneath my belly and lifted me up on all fours, I cooperated with this move. She positioned herself behind me and lowered her head towards my ass, her tongue was doing magic on my ass, i was lost in the sexual moment that I never knew existed. Her tongue was soon replaced by a finger then two. The moment of truth arrived. She whispered in my ear "I'm gonna fuck your cute little ass". I just looked at her and smiled, Her fingers left my ass and I could feel the mattress movement that she was positioning herself behind me to fuck me. I closed my eyes and waited for it, I was afraid, yet I was excited about all this. she pressed her dick against the entrance of my ass, she brushed my ass cheek and said relax, you are going to love this. She pushed in and I bit on my lower lip, i thought to myself, she is big and there is no way she is going to fit that thing in my ass. She continued to push and I could feel she was making progress. Suddenly she stopped pushing and held still for a few moments, then she started again the movement but this time pulling out rather than pushing in. Then she pushed back in, this continued very slow, pushing in more and pulling back a little. I was getting used to her cock filling my ass by now and for what I found as a very strange reason I was enjoying this to a point where I heard myself encouraging her to fuck me. She reached around and grabbed my dick and started stroking it with the same rhythm that she was fucking me. I was besides myself, I started screaming and telling her to fuck me good. I reached a point of no return and announced that I was going to cum, she started pumping my cock more faster with her hand while she also increased the speed that she was fucking me with. I could not take it anymore and I just let it go, streams and streams of cum left my cock and I felt her getting tensed behind me when she also came with me. We stayed that way for sometime until we collapsed on bed with her on my back.

After catching our breaths, she was the first one to talk. She said that she was sorry about what happened, she knows it wasn't part of my plan to be fucked in the ass tonight. I said no need to be sorry, while this is something I never thought i will ever do, it is something that I never knew can be so good. We laid side by side cuddling, kissing and smiling a lot. We both fell asleep in each other's arms and woke up at 05:45 when the alarm on my phone went off. she disappeared under the covers and gave me one of the best morning blowjobs I ever had. We both took showers separately and we left the hotel and she asked me to drop her by her flat in Sunyside before I get to class. We planned to hook up again soon but so many things were happening in a very short period of time that I had in Pretoria I never made time.


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