A year after I had my first time experience with a strap-on dildo, I haven’t sat still in the meantime. I had several one-night stands, only satisfying my ass still remained a bit taboo. You can usually tell when having sex with a woman if she is a bit open-minded and/or dares to ask. Every time that I did dare to ask, the answer was negative. Too bad, but unfortunately.


At home, of course, I still continued to masturbate, and I began to use my ass more and more often in this game. If desire is not fulfilled during sex, then let it be during masturbation, right? As time went on, I started to push my limits again. Strapon movies started to become more and more shemale movies, and although at first I thought it was a bit gay, later I thought “what the hell”. A Shemale feels like a woman after all, and apart from a penis, most of them, can pass well as a woman. Some shemales are even more handsome than many women and thus very arousing, so there was also a lot of semen sprayed at my side.

Time passed, and I went looking for a pub or tent where shemales came, and wanted to see if they were as beautiful as on the internet. After some searching and googling, I had found an address and drove there Friday evening. Upon entering, I was amazed.

Beautiful shemales were chatting with women and men.

Beautiful shemales were chatting with women and men, all very quiet and relaxed. Sometimes you really had to look closely to see whether it was a woman or a shemale and sometimes they had the stubble on their faces, so it was an evening game. As I sat playing my game at the bar, I felt something wet against my back. Damn, I thought, another guy who is drunk and spills some beer again. I turned a little angry and looked straight into the eyes of a cute girl.

It actually shocked me a little because I was angry but quickly looked more gallant. She apologized and said, “Can happen, luckily it’s a pretty woman and not a drunk guy”. Of course, she liked this, and we got to talking. Her name was Chantal and she had come here with a friend. I was naturally curious and asked what she was doing here in this “shemale” club. It turned out that this turned out to be her friend, and I spontaneously said, “Oh? Nice!”. After some flirting from my side, Chantal started to flirt a little bit back and I thought: “Am I going to a shemale bar, I’ll end up in bed with a woman after all, haha” a funny thought in itself.

As the evening progressed we became more and more free and after some dancing, our mouths touched. She kissed quite wildly and immediately grabbed me by my ass, she said: “if you say more sweet things I will take you home, so be careful!”. I laughed of course and said “you are the most beautiful woman I have seen in ages, and your ass is to write home about”. This probably hit home because within half an hour I was in the car with her. Once we got home we continued on the couch where we left off in the pub and tongued a lot. In no time she took off my t-shirt and sat on my lap dry-humping my cock. Of course this horny thing made me super stiff, especially when she said: “Oooh I feel something nice pressing against my ass”. I grabbed her buttocks and said, “I have a pair of ridiculously beautiful buttocks in my hands” and squeezed nice and hard. She groaned and began to open my fly.

After she opened my pants, her tongue made its way down through my nipples and slurped my hard-on nicely. She moaned that it was good, and this put me at ease. She wetted my boner nicely by spitting on it a few good times before taking it deep into her throat. She went on like a pro, and I had to struggle not to squirt right down her throat. While she was busy, I pulled up her sweatshirt and freed her breasts from her simple but super exciting bra, a white one of fabric that showed many contours of her nipples. She definitely had a big C or a small D, so exactly 2 handfuls. She continued blowing me for another minute or so and then sat back on my lap giving me instant clearance to her breasts. Licking like Lassie they always say, well this I did haha. She started to sigh and moan and said, “Ooh how nice you lick my nipples and what a nice cock you have”.

She grabbed it and started pulling on it again gently. She sighed very deeply and then got off me and sat down next to me. She said, “Do you really find me handsome?”. I agreed wholeheartedly and said she really was the most beautiful woman I had seen in ages. She said, “That’s sweet, but know…. that friend who was with me”. I immediately said, “Oh yeah, I haven’t seen that one at all!”. She said: “no, that can be right because I was alone”. It had to sink in, but 5 seconds later 1 and 1 became 2.

I said: “So you are a shemale then?” and shyly she said yes.

I was a bit shocked because I had not prepared myself for this. I quickly recovered because I could see it wouldn’t be long before she ran out of the room. I asked her if I could feel and with a brief nod of agreement, I put my hand on my pants. My open-minded thoughts took over and with a small smile began to tongue her again and rub her pants nice and slowly. I felt the joy as my tongue was almost sucked in. She was getting very hard and felt she had a bigger penis than me. I opened her pants and saw her happy face.

I started quietly, step by step as I had to get used to the thought. I started playing her nipples with my tongue again, and quietly I took her penis out of her hipster. By the way, just as sexy as her bra. I began to gently jerk her off and it just got bigger and bigger. At least 20 cm and half a time thicker. I said, “You are huge for a horribly delicious woman haha”. She giggled and said, “That doesn’t mean you don’t have a nice cock yummy”. Surely I found this flattering and this gave me the boost to go for it!

I slowly moved down and kissed the tip of her penis.

I felt her breathing quicken and her hips shoot up slightly. This was the go-ahead and I started sucking her wildly. I didn’t know at all what exactly to do, only did what I myself would enjoy. Seemingly it struck a chord and she started thrusting and moaning even harder. This continued for a few minutes until she told me to stop or she would cum. I said, “Then you are out of luck” and continued at an even faster pace. She moaned even louder and screamed that she was going to come. Then I felt, for the first time in my life seed shoot into my mouth and it was quite scary I must say.

I kept it all in my mouth and then swallowed it in one go. She laughed and asked, “What was it like, cum in your mouth for the first time?” I said it wasn’t too bad and that it was kind of horny. She hugged me and grabbed my penis hard and said, “your turn will come soon, I have to get ready first.” I got up too and followed her and she looked at me funny: “I’m going to clean myself up hear so you can fuck me in a moment”. I said, “Yes but I have to be clean then too, don’t I?” she looked at me in surprise but very happy and said, “can I join you then too?” I said, “of course only I don’t know if I will get something that big in my ass”. She reassured me and said she would go easy on me, almost jumping a hole in the air.

After we both rinsed our asses for a while, we ended up on her latex bed. We tongued fiercely and she took my hard-on in her hand again. After some tugging, my penis was back to full war strength and she went to her nightstand to grab lube. When she did this she turned her ass toward me and I saw my opportunity. I turned her on her stomach and put my mouth on her buttocks. She moaned and asked, “what are you doing now?” and I said “I’m going to lick your ass real good”. She said “my luck can’t run out tonight!”.

I started with her ass, but soon my tongue was halfway up her ass.

I started with her ass, but soon my tongue was halfway up her ass. I would never do this if the person was not clean but it had been 15 min since we had rinsed it clean. Moaning and getting stiff again, she said I could fuck her. I grabbed her lube and put it on my penis. I put my penis against her ass and slowly pushed harder and harder. This was seemingly too slow for her because she went up at once and pressed her ass against my penis. She moaned loudly and began to jerk herself off. I pulled her hand away and did it myself. With some lube I also let her penis slip nicely between my fingers and put some lube on her hand. She asked me what to do and I told her to finger me.

With my penis stimulated in her ass, her penis through my hand and 3 fingers in my ass we fucked on like animals. I said that at this rate I was going to come soon and she said, “Then you are out of luck” and she pounded her ass back even harder and pushed a fourth finger in. This became too much for me and with a big moan I squirted a big load of cum into her asshole. We plopped down side by side and she started fingering her ass and licking fingers off. She looked at me hornily dropped a long string of cum into her mouth. When her mouth contained all the cum from her ass, she looked at me even hornier and came on top of me. We tongued me the cum between our mouths and made my penis rise again.

Then she sat down between my legs and grabbed the lube, with this she began to lubricate her penis and my ass well and then grabbed my legs firmly. She pushed my legs up so that my ass was wide open and her penis was free. Her four fingers had been effective because my ass was nice and wide open. Still it didn’t go that easy because that enormous penis caused some resistance. Fortunately, after 5 seconds, I could relax completely and Chantal’s thick and long penis flopped inside me. This made me so horny that my penis became rock hard and because she had seen this she said: “Do you like it that much, my horny kinky stud?” I nodded and she grabbed my penis.

She started jerking me off hard and fucked harder and harder. At one point she took it out completely only to ram it back in hard. This felt very horny and also felt a bit like a victory because I had crossed another boundary haha. After a few minutes of hard fucking she cried out that she had to cum and I said: “You may choose”. She had chosen quickly because she said right away, “I want you to finger me with four fingers while I fuck your mouth.” I nodded and she pushed her penis deep into my throat. I knew this was a horny feeling for her because I love that too. I gagged a few times before I felt the seed shoot down my throat again. She said, “keep it in your mouth and don’t swallow!”. I kept it in my mouth and meanwhile I was being sucked hard and she made me cum deep in her throat within 2 minutes. Tonguing with our cum and our gaping asses, we later got into the shower and fell asleep deliciously. The morning after, we made love again and exchanged each other’s numbers. A night never to forget.