Home >> SheMale sex Stories >> Story : First time and what great fun
     By Trollkeen. You can rate or review this story.

My name is Jakub, or Jake as my friends call me. At the time this little adventure took place, I was 20 years old and I guess I was a pretty lonely guy. Overall, I am a pretty average dude: 6 feet tall, slim body and average looks, the only thing about me that’s a bit different than most people I know is that I am very shy. I suppose that this was the reason that made start looking for companionship over the Internet. I was just hoping that if I can impress someone with my personality, then I wouldn’t have to worry so much about what they thought of my looks; even though I’m not bad looking, a low self-esteem will make you think that way. 

So I started meeting some girls through the net. A couple of weeks passed and nothing really happened so I started looking at more than just regular places to meet regular girls. Now, I should mention that I have never in my life, to that point, had any relations with men but like I said, your mind starts to wonder when you’re lonely. There were times when I even began to fantasize about having sex with men, but I have never had the guts to do anything about it. And what more, I have never really been attracted to any guy. But then I found something that really got my attention, shemales. Looking at these, mostly Latino, men with pretty feminine faces, long smooth legs, big butts and breasts just drove me crazy. Many of them were so feminine that you couldn’t even guess that they are really men, until they loose the panties of course. Looking at these beautiful shemales made me realize that I was never attracted to men unless they were very feminine looking, but I have to admit that I definitely have a thing for penises. I think that this excited me most just because it was so wrong. So then I finally arrived at a chat room for the transgendered and all alike and met Lucas. 

From his description I painted a picture of a guy about 5 feet 10, thin build with long flowing black hair. We chatted for a bit and as soon as we found out that we both lived in the same city we were automatically attracted to each other. He told me that he is a shy and very feminine boy and that sometimes he dresses up as a girl, which to his liking and later mine, he not only feels great in but looks good too. When asked which he prefers he said that he was born and lives as a boy but deep inside he was meant to be more than that. I have to admit I was not only intrigued, but I had an erection the entire time just talking and thinking about the possibility of meeting this guy. So we set it up. I was scared and thought that I’m probably going to chicken out at the last minute, but it was all way too exciting not to at least consider. The plan was to help each other fulfill our fantasies and so when we met the very next day, I showed up as I am, a guy looking for not only a good time but possibly something more; and to my great and pleasant surprise, “he” was a beautiful woman. I walked up to the car she was leaning on very slowly and absorbed the entire view.

Cute little black shoes on a small heel showed perfectly painted pink toenails; her feet were small and nicely curved which looked very sexy. Long and smooth legs were bare up to the knee. She had on a colorful summer dress, which exposed the back; smooth arms were also bare except for a cute bracelet. I think the biggest surprise were the hands, which were also very feminine and delicate with nails matching her toes. After all the best way to tell the difference between men and women are the hands and feet, everything else can be changed or covered up. I knew that the breasts I saw was just a stuffed bra, but that didn’t stop my imagination from taking over and I got really excited. Smooth long neck led to a pretty and again very feminine face, big brown eyes had a certain intensity in them and the long black hair that had a hint of dark red in them were flowing over her shoulders and half way down the back. To say the least, I was mesmerized. If he hadn’t told me before that he was a guy I would not have guessed it. He had on a tiny bit of make up that slightly accented his already very womanly face. I was so scared and nervous that the only reason I hadn’t chickened out was the fact that I was really attracted to the girl I saw in front of me. 

“Hi, I’m Lucy.” she said extending her hand slightly. I took her hand and shook it lightly while saying hi in return and introducing my self. We both just stood there for a moment and looked at each other, neither of us knowing what to do next. I was completely amazed at how her handshake, her voice and even every little mannerism did not betray her true identity or I should say her gender in any way. As we planned the day before, we got into the car and drove down to the park where we sat down at the most secluded bench we could find. In the car we kept mostly to small talk and every awkward moment of silence has made both of us blush. We were both so shy it was just freaking me out to the point that I thought we would never get anywhere. Once outside it got a bit better, again on the way to the bench I was amazed that the way she walked was more feminine than many girls I know, I realized that maybe he overplayed his role, but he felt more confident this way. We were both glad to see that there were very few people in the park and so we sat close to each other and finally started to talk. Right of the bat I told her that she looked breathtaking and I couldn’t have imagined her looking more sexy. 

That seemed to have broken the ice because again she blushed and it seemed that she was waiting for that confirmation from me. After that, the conversation took of and for the next two hours we covered almost everything. I learned that we had lots in common and we were both virgins, which for some reason gave me more confidence as well. Soon after that the conversation steered it self to sex and it wasn’t long before I noticed that in answer to the slight bulge in my jeans, Lucy also had a small bulge in her crotch that she quickly covered by crossing her legs. This didn’t help me much as it revealed more of her smooth sexy legs and my hard-on got to the point that it was painful. She could see this and thankfully she brushed it off with the cutest smile of the day and said it was okay. After I shifted my position a bit I took her hand and told her how beautiful she was and that I wanted her very badly. She was looking deep into my eyes when I said that and she blushed once more when she realized how serious I was about her. At this point she had no more reservations and neither did I, there was no more holding back and we were about to kiss when some people went by so we decided to go back to the car. 

Right then I realized that it didn’t bother me at all that we were seen by others, after all I was the only one who could possibly know that the gorgeous woman next to me was hiding a throbbing penis between her legs, but it’s not surprising that she felt uncomfortable since this was her first time out in public as a woman. To my surprise we weren’t driving anywhere yet, she opened the back of her mother’s minivan and we went straight for the back seat. She closed and locked the doors and windows even though it was pretty hot in there, then sitting down she said that she lives only with her mom and that she’s out of town so we can go to Lucy’s place but first she had to try something. Right then my hard-on returned in full girth as she placed one hand on my thigh and with the other she turned my head to face her and placed a small kiss on my lips. I almost came right then. I couldn’t believe the electricity, the sexual tension. I kissed her back, slowly at first and then we started to make out. It was hot and very passionate, like you would see in a Hollywood movie when two people finally get together after a long time of longing for each other. Soon our tongues were slithering in and out of our mouths. She stopped it for a second so that she could raise her self and sit in my lap with her legs spread on either side of me. Now facing each other perfectly she pressed her self to me again and we embraced in another long and dirty kiss. 

At this point we were literally licking each other’s faces and messing up our hair. My hands were all over her legs and then finally her perfectly round butt. I raised her dress and felt the soft cool skin of her buttocks but it was the feeling of the tiny panties trying to cover them that really drove me crazy. This time I stopped the kiss and she asked what was wrong. I didn’t answer because there was nothing wrong; I just had to unzip my pants ‘cause I was in a lot of pain again. But she stopped me and said that she would get it for me. That’s when she slid down to the floor and unbuttoned my shirt. Slowly she bent down over my chest and caressed my nipples. With a sly smile she began to slowly and very passionately kiss and suck on them. I never got any kicks out of pleasuring my self that way, but then again I never had that done by someone like her. This entire time I was in heaven or at least I hope that heaven feels something like this, I forgot completely that she was actually a boy and just lost my self in the fantasy that we promised ourselves. She continued to pleasure me in ways I’ve never experienced being a virgin and I knew that it could only get better. Just then she finally loosened by belt and unzipped my jeans, the relief was great. She slowly caressed my cock and kissed it through the fabric of my underwear. The entire time she had her eyes fixed on mine and the cute smile on her face continued to drive me crazy. Once she got my underwear down, she held my penis in her soft hand and with a grin lowered her mouth onto it. Nothing was said the entire time except her occasional giggle or moan, and the very soft slurping sounds. I could tell that she had no experience in this but it didn’t matter. Her passion for the experience and her warm, wet mouth were more than enough. 

A few minutes later I said that I’m cumming and I moaned louder than ever as I came into her mouth. She didn’t stop for even a second but some leaked out of her mouth as she was trying to swallow up my cum. She paused briefly to swallow what was still in her mouth and then continued to suck on my member until it just flopped out of her mouth. Needless to say it was just about the best thing I have experienced until then. We decided to go over to her place right after that since her place was empty and would be for the whole day. The drive took only about 10 minutes but even that seemed too long to wait. 

Inside we cooled off a bit. She showed me around and even brought some wine for us to drink. The whole time we were holding hands and kissing, occasionally I grabbed her ass and made her giggle. When we kissed I could still pick up the musky taste of my cum. After about 20 minutes and almost the whole bottle of wine we made our way to her room in the basement, which to my delight seemed not only nice and clean but prepared for the occasion. It wasn’t long before we were sitting on the bed making out again. I noticed that her room was actually meant to be a gym because of the big mirror across one of the walls. It was also decorated in a very neutral theme that was fit for both guys and girls. I decided that since she already got to enjoy my body earlier, it was now my turn and I took my time. 

I laid her down and told her to just relax and enjoy herself, which she did. I started with her feet. At first just kissing them and then licking and sucking on her pretty toes as I took off her shoes. She seemed to enjoy that a lot so I made it a point to take it slow. As I continued up I made love to every part of her body, which I should say was just damn perfect. I loved kissing and licking her calves and her thighs, but I didn’t go higher just yet. Along the way I took off my socks and shirt and then I kissed her hands and neck. When she sat up I began to slowly remove her dress. The black bra she was wearing was stuffed with some kind of soft cloth that felt like silk or something like that. I left it on since it looked quite perfect as it was and I enjoyed the elusion. Besides, they felt nice to the touch and the reflection in the mirror showed a perfect woman. 

I removed her dress and finally exposed her panties. The bulge was barely noticeable but I knew she wasn’t hard yet. I kissed her stomach and her belly button, the whole time squeezing her smooth buttocks and thighs. Except for her head of course, her entire body was perfectly smooth and hairless. She also had a very nice tan I hadn’t really noticed before that made her look really hot. It wasn’t until she felt my warm breath on her crotch that the bulge in her black panties started to grow and finally I saw the tip of her penis poking out of the top below her belly button. I pulled her panties down and before she said anything I slowly put the tip in my mouth. I remember that I instantly started salivating like if I just ate a starburst candy. Her cock was about the same size as mine, that’s about 6 inches and proportional thickness, but it was very soft while mine gets a lot harder.

 At first it was a bit awkward because I wanted to make sure that she likes it, but then I relaxed and started to take more of her inside my mouth. The whole time I would just lick and suck the tip as best as I could. She lasted less than 5 minutes and then warned me that she’s about to cum, but that didn’t leave me much time to react and she came in my mouth. I hadn’t planned on taking it in but once she came I didn’t stop sucking and she filled my mouth with her sperm. When her orgasm passed I considered my options and decided to swallow; after all, you shouldn’t knock that which you haven’t tried. The taste was actually not too bad, it really is a salty and musky taste like everyone says, but while swallowing I almost gagged. I guess it’s something you just have to get used to. 





Lucy laid down on the bed still moaning from her orgasm while I got ready for what I was waiting my whole life it seems. I got the lubricant she took out earlier and applied it to my hard cock. Then I raised her legs in the air and placed them on my shoulders while applying the lubricant to her pink anus. She moaned lightly as I inserted my forefinger and then the middle finger getting as much lubricant inside as I could. With her legs still on my shoulders and me kneeling on the floor I put the tip of my penis against her asshole. She shuddered in anticipation and I thought of using a condom, but since we both trusted each other I decided against it just so I could feel the full ecstasy not hindered by the rubber. I slowly pushed in and again Lucy moaned. Once the head was in, I stopped for a bit so she could get used to it and as soon as she relaxed I began to go further in. The feeling was awesome. It was very tight and hot, and every time I moved back out it tightened around my cock as if she didn’t want my cock to leave creating even more pleasure for me. 

She said that it hurt but since I took it real slow she didn’t tell me to stop. Soon I could feel that she got used to it and the pain subsided so I picked up the pace. Before long I was literally fucking her. She moaned a lot and I noticed that every time she screamed her voice was a little bit different than before. A few minutes later I stopped and pulled out of her, then I lay beside her and we embraced in a kiss. She then got on her knees and hands and I knelt behind her. After putting on a bit more lubricant I entered her from behind in the doggy position. It was more comfortable for her this way and so I fucked her again as hard as I could. I knew I wouldn’t last long like this and Lucy was screaming again, her voice was sounding even more like a guys but it didn’t bother me since I was in pure ecstasy. Just a few short minutes into it I looked into the mirror and the side view of us drove me over the top and I started to cum deep into her ass. With every squirt I plunged my self as hard and fast as I could making a loud slapping noise as my crotch collided with her round ass and my testicles slapped against hers. 

I think that it was the sight of her half hard cock flopping back and forth with every thrust that drove me into the most powerful orgasm yet. I kept thrusting in and out of her until I was too tired to continue. Then I finally pulled out and dropped on the bed while Lucy just melted down beside me still moaning and breathing really hard. When she caught her breath back, Lucy went down on me again and licked up some of the sperm that was still leaking out of me. Then she slowly left the room for a few minutes. 

When she returned, I noticed right of the bat that she was very different. The makeup and bra were gone, her hair was wet and tied back, and the way she stood in the doorway stroking her hard cock told me that Lucy was gone and Lucas has come to play. At first he had surprised me, but then I surprised my self. Even though we agreed that I was going to be with Lucy tonight, I smiled and waved Lucas over to me. He was glad to see me approve and came over grinning at me. “I’m gonna love you like you’ve never been loved before.” he said in his regular but still rather high pitched voice and he sat down in my lap pressing his hard cock to my chest. We kissed for a few minutes until he took charge and laid me down on my stomach. I knew what was coming and I started to tingle all over with anticipation. I almost jumped up when he suddenly stuck a finger covered in cool lubricant into my asshole. After fingering me at first with one, then two fingers, he told me to relax and stick my butt up in the air. 

As I did this he placed a pillow under my stomach and I laid down in a position that perfectly exposed my virgin ass to him. Seconds later the tip of his well-lubricated dick was spreading my anus. I learned very quickly that less I resisted the less painful it was so I just closed my eyes and let it all happen leaving my whole body as loose and relaxed as I could manage. He took it slow and went a little further in with every push. I concentrated on the reflection in the mirror to take my mind off the pain, what I saw I couldn’t believe. Lucas knew from the lack of my moaning that I was in a lot of pain so he pulled out and told me to lie down on my back with my ass on the pillow. I obeyed him with out question and he spread my legs apart and lifted them in the air. Now I felt even more vulnerable but as soon as he entered me again I realized that the pain was almost all gone. 

Shortly after he was leaning over me looking me in the eyes and fucking me so hard that I was screaming. But it wasn’t because of pain. Every time his cock pushed against my prostate I felt a rush of blood and excitement pulse through my dick and balls, the sensations were so incredible that I started to get a hard on again. I have heard that the stimulation of the prostate is the best part of anal sex but I never thought it would feel this good. Looking in the mirror I saw just how hard I was being fucked and I noticed that my cock was leaking a lot of precum, which has never happened like that before, I was gonna cum again soon. At the same time Lucas slowed his pace but his thrusts got more powerful and he was drilling deeper inside me then ever, the look on his face told me that he was cumming. He came for a long time and didn’t stop fucking me for more than five minutes. Between his moans and mine, I barely noticed that I squirted hot semen all over my belly button. When Lucas finished, he pulled out of me and let my legs down on the bed. It was then that the pain of being fucked so hard came back, but even worse was the feeling of emptiness left by his cock. I almost asked him to go back in but I knew that we were both way to tired to go on. 

Needless to say I got fucked and I loved it. Lucas had a big smile on his cute face as he slapped his sperm drenched cock onto my face. I took it into my mouth and sucked of all his cum enjoying every bit of it. During this I stuck a finger into my asshole and found that it was not only stretched and very soft but it was leaking Lucas’ cum all over the bed. Lucas pulled his now shrunken cock out of my mouth and turned around, then to my surprise he dipped his dick and balls into the sperm that has pooled on my belly button and moved his genitals right over my face so that my own cum was now dripping down on me. I licked and sucked up all of my own cum and was begging for more while he cleaned up the sperm on my stomach. Shortly he began to suck my balls and I got brave enough to try something I wanted to do for a long time. Since we were locked in a perfect 69 he moved down to give me access to his asshole and I made love to it. First I licked and kissed it then started to stick my tongue inside as deep as I could. 

When he saw that he wasn’t going to get any more reaction from my cock, he sat up to give me even better access and really started to enjoy the attention I was giving his anus. After fingering his ass for a bit I was rewarded with a bit of my own sperm dripping out of it and I licked it up without a moments hesitation. At that precise moment it really dawned on me what has just happened. Until now it was more like some unreal fantasy, more like a dream than anything. But now I see that this morning I was a lonely, straight, virgin guy looking for some excitement, some change in my life; and now I’m lying here licking my own sperm out of some guys asshole and my own ass is burning from being fucked like a cheap hooker. I stopped everything and just lay there absorbing this moment with a smile on my face. Lucas climbed off of me lay beside me embracing me in a soft hug. My ass was now in a pool of cum and lubricant, I could feel the sticky cum on my stomach and my face too. We were both lying on our sides looking into the mirror; tired, hot and sweaty, the smell of dirty sex was filling our nostrils. 

We hadn’t said a word for a while now and not wanting to break the peaceful silence I kissed the back of Lucas’ neck to tell him that I definitely approve of all that has happened today. His answer was the very same cute smile he gave me earlier in the park. That’s when I started to see him differently again. I no longer made any distinction between Lucas and Lucy; they were one and the same person. The genitals and the lack of breasts showed a boy, but the feminine body, gorgeous face and female mannerisms created a woman that none could second-guess. We lay like this for a while, enjoying each other’s company and not saying anything. We both felt complete. 

Later we took a bath together where we washed each other’s bodies and kept on kissing and hugging the entire time, we just couldn’t get enough of each other. When the time came to say goodbye, we were both very reluctant to separate; but we did finally exchange numbers and I left for a pleasant walk home. Well almost completely pleasant since my ass was still burning from the abuse it received earlier. The whole time I walked I thought of nothing more than the soft skin of the beautiful boy I made love to that day and I couldn’t wait to see him again.





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Categories >> Erotic sex stories | Gay stories | Lesbian stories | Shemale sex stories                   Author : Trollkeen

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