Shemale Stories

This horny story was posted at our forum by a guy named Capablanca who seems to have finally admitted he prefers playing with shemale cocks over playing chess. 😉

I have already described my first encounter with a shemale – an amazing experience. One thing I’ve been looking for since that first experience is a shemale who would cum in my mouth. Now one might think that this wouldn’t be too hard to find, but in fact it is a bit difficult. First of all, the only shemales I’ve been with have all been escorts (I’ve seen five different ones so far, all in Toronto). I’ll mention by the way that I really wish I’d gotten into escorts when I was younger -I’m well over 40 now, and I don’t think I could get a shemale for free to save my life. Sad, but true. Anyways, escorts don’t like to orgasm with a customer until their last of the night – they have to keep themselves a state of arousal through the evening. And I’m not a late-night person. So when you add all this together, I was having no luck at all in my ambition – until this Saturday.

I was allegedly at the office working – in fact, I did come in and do some work. But I foolishly logged on to the web, and surfed through the Red Zone, Eros and so on, looking at various shemales. The urge hit me, and in no time I was on my cell phone, looking to see who was available. I made an appoint with A___ (I won’t give her name here). And off I went to downtown Toronto for some fun.

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• My first taste of shemale cum

Another work of art of a shemale lover. Props for this wonderful romantic story go to our forum member Ila.

It’s a cold, windy, and snowy evening. My lady and I are in the bathtub together. The water is still very warm and the scent of bubble bath still lingers in the air. I have just bathed her and now I am shaving her legs. She loves the attention I pay to gently washing her and at the same time massaging away her aches. The bath has relaxed her and as I finish her legs she leans over and kisses me in anticipation of what is to come.

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This Ode to shecock was posted at our forum by a great guy Ila. It pretty much sums up the feelings of all ladyboy lovers and I can’t think of better words to express love for shemale cock, he already brought it to perfection. 😉

I think about having a shecock in me just as often as I think about sucking cock. I want to feel hard shecock sliding in and out of me. My ladyboy would start by bending me over and then stimulating me with her finger touching and pushing against my anus. She would then lube me up and gradually work one then two fingers into me. When she could feel me loosen up a little she would start to tease me by rubbing the head of her cock against my anus. This would get me quite aroused and excited and I would start pushing back against her cock. She would then push her hard cock a little ways into me and withdraw. She would do this a few times until she got the head of her cock all the way into me. As she got the head of her cock into me I would clamp my sphincter muscles tight, but she would stay still and wait for me to relax the pressure. As soon as she felt me relax she would slide her cock in a little more and slightly withdraw. I would again tighten up my muscles and she would wait for me to relax again.

We would continue like this until she was all the way in me. She would then start stroking her lovely hard cock in and out me; slowly at first and then building up to more force and speed. I would be loving it and pushing back against her to meet her forward thrusts. After several minutes of this she would completely withdraw from me so that I could turn over onto my back. She would then get in between my legs and again penetrate me with her rock hard cock. I would wrap my legs around behind her to hold her into me. She would continue to stroke in and out of me and in no time I would be spraying a big load of cum onto my belly. She would cum right after that emptying her load deep into me. As her cock softened and slid out I would feel her cum start to dribble out of me.

Neither of us would be finished yet so I would turn around and lay on my stomach. She would then spear me for the third time with her love shaft. After a little while she would empty another load of cum into me. By now my asshole would be tender, but her beautiful hot cum dribbling out would soothe the ache away. As I stood up to turn around and kiss her the dribble would turn into a major leak and start to run down my leg, but I wouldn’t care because I love the feel of her sperm anywhere on me.

Wow do I ever need a shecock in me now. I’m aching for the taste and feel of cock. I want lots and lots of shecock.

Again an awesome reader submitted story. One of our lucky readers says he had a great fuck with Ladyboy Jane.

Was in BKK in Oct 07 looking for love in all the wrong places. In particular one sexy cum kitten called Jane from Guess bar, Sukhumvit soi 1. When i arrived i found a complex of beer bars but no Guess bar. Just as i was about to give up i spotted an LB at a little food bar so i asked her she smiled and said come with me. Guess bar was upstairs hidden away but she led me right to it. Alrighty time for fun i thought hehe. No sooner had i entered and ordered my JD & coke who should i spot? No other than my target for the evening Jane. She was just stunning: long legs, awesome tits and face to die for. She snuggled up to me and started caressing my ball bag whilst looking me in the eyes with that fuck me baby look she holds so well.

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Another little surprise for You, a real life story by our reader Stu.

I recently visited a shemale. She had the most fantastic body and a very thick cock of about 7″. But most impressive was her lovely brown asshole. Once I sucked her cock to hardness I just had to rim her for all I was worth. She could contract and dialate her anus as my tounge licked and prodded her. All the time I was wanking this big hard cock.

When I mounted her and pushed my cock deep into her ass she griped it with her ass muscles – very exciting. I didnt want to cum too quickly so I pulled out for another suck of the now glistening with precum cock. She fingered my hole and I invited her to fuck me. Although her girth did sting a little at first I soon loosened up and encoreged her to fuck me as hard as she could. My god could she pump deep and hard!!

Do you want my cum she asked – Oh yes came my instant answer at which point she withdrew and presented her throbbing cock to my mouth. Needless to say I took the lot to the back of my throat. I tried to wank while this went on but was told that I would get a special treat if I resisted. She lubed up her hand and pushed four fingers into my still gaping ass and told me to relax. I did so and felt her whole hand slipping into my ass. I had never been fisted before but the earlier fucking and admitedly small hand did the trick. There is nothing like the power of ones cum when a fist is up you and you are looking at a beutifull shemele!!!

Next visit we are going to play with watersports and I am promised no pissing till I get there on that day – I cant wait!!

Here’s the second part of the story posted by our reader Tommy, and i’ll tell you what, it’s even hotter than the first one!

I went back to Casanova some months later, hoping to see that well endowed ladyboy. She was dancing on stage – we made eye contact, she hopped down straightaway and we kissed, while our cocks gently rubbed into each others!

Her name was Yoko. We did the deal and headed back to the hotel not wasting any time. She bounded into the room and in no time she was on the bed, panties down and me sucking her gorgeous dark pointy cock upright. I had no idea where this encounter was going to go, but when she asked me if she could fuck my ass – well – a gentleman can hardly refuse.

She pushed me face down on the bed and lubed my ass and got to work with two fingers to get me loosened up. She tried to enter me – it didn’t work well plus I wanted to see everything – so I rolled ono my back, raised my legs, presented my virgin asshole and soon I felt a first ever cock probing my bud. She slipped in, taking plenty of time to let my ass adjust, and soon got into an amazing rhythym and fucked me solid.

We then swapped over – and for the first time in my life I could see my cock sliding into an asshole – every dream coming true. I couldn’t help myself and came quite soon. The whole thing was like something out of the most amazing dream – gorgeous woman with a great smile, awesome tits, willing ass and a hard cock – what’s not to like about that!!!

Feasting comes after fasting. What’s with you guys, it’s been over a month that i haven’t seen any new shemale stories from you, and now i’m getting them every day. Which is good of course. 😉 Here’s a shemale story from Tommy about his long-standing shemale fantasy finally fulfilled.

I’d had shemale fantasies for years, and when my job started taking me to Bangkok I walked around Nana Plaza a few times, spotting what I was sure were ladyboys outside Casanova Bar. Once I even went in and had a drink – you know what it’s like there – in no time at all you’re surrounded by hot ladyboys flashing tits, rubbing your cock etc. I had a drink with one and shyly touched the bulge in her panties – that’s all I did that time having freaked myself out!

Months later I went back and met a beautiful ladyboy Natalie – the most gorgeous face, tits and flat tummy that just blew me away. We went to my room in a nearby hotel. She was really lovely and had a small cock that I couldn’t resist sucking – it didn’t get hard but for a first taste was delicious! She gave me absolutley the best blow job of my life – I shot a load in her mouth, she gagged it out on her chest – I kept cumming on her tits – have never seen so much of my own cum ever.

Anyhow, backtracking to Casanova – while Natalie was getting dressed to leave with me another gorgeous busty ladyboy sashayed up to me and told me that her cock was much bigger than Natalie’s – she even showed it to me! I told her I’d be back in a few months – indeed I did and that’s another story… 😉

Another little first timer’s story and 5 minutes of glory for our reader Greg.

I remember my fist time like it was yesterday.

We met at a bar the most beautiful woman i have ever seen. A the end of the night she asked me for a ride home so natrally I gave Her one. She looked so hot in her tight short black dress. When we got to her house she asked me in for a drink; of course I accepted. After a drink or two we began to make out with one another which led to me geting the best blow job of my life. She knew exactly what I wanted.

I started to take off her dress and sucked on her tits down her tummy when she says I have to tell you something. After she told me she was a ladyboy. She was shocked that I wasn’t running for the hills. I told her that just ment that she was about to fulfill my most wild fantacy then took her dress all the way off to expose her huge hard cock, which i sucked and played with untill she came in my mouth.

We had sex with each other all night many diffrent positions and places in her house. But my fav one makes me hard just to think about it is I was in her sweet tight ass with my hard cock from behind, while we were having sex she turns her head to me and we begin to kiss while i am feeling her perfect tits and nipples with one hand and jerking off her big sexy hard cock with my other hand. We continued to make love in this position untill we both came. Which was at the same time. Truly was an amazing night that i will never forget.

This little nice story was posted at our blog today by a guy who calls himself “Shemale Horny”. Enjoy reading.

I was in the army stationed in Hawaii. My friend took me to a club down on Hotel st. We got a little buzzed but i remember there was some of the most beautiful women there or so it seemed. One of them was giving me the eye so i went over to her and bought her a drink.

One thing led to another and we ended up at the motel. We started with foreplay and then she wanted to suck my dick and it was the best blowjob i ever had. After that i must have dozzed off for awhile because the next thing that happened changed the way i feel about shemales forever…

Back to the story, i was on my stomach butt-naked with her on top of me fucking me in the ass saying i know you like it don’t you, and i replied fuck yea!!! I could not belive it but i loved it. I ended up fucking and getting fucked the rest of the time i was stationed there. I love shemales her name was Peaches. I am married figure that,but every time i cheat it is with a shemale. I guess i love them because i see them as a better woman.

This story that was posted at the forum today by our new member got me hard as hell. He writes about his first experience with a tgirl and i can’t be more positive that most of us would like to experience this too. Enjoy reading…

I recently had my first experience with a shemale. Here’s how it happened.

For the last few years I’ve being seeing escorts, and I search for them online. I noticed ads for shemales, and they looked pretty hot. Didn’t think anything more about it, though, for a few months. One evening I was seeing a girl I’d seen a few times before. She was complaining business was down – was losing trade to shemales! It wasn’t long before she lost another one: me.

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• My first time with a shemale escort