Shemale Date

In the early days of the internet, dating sites started appearing. There was one that I used to meet women and whilst it wasn't as popular as others or as famous as today's well known sites it worked for me. I soon found internet dating an interesting place as I realised that people could write anything about themselves but turn out to be completely different in person. One woman I met turned out to be a very skilled dominatrix, but that story is for another day, today I am going to talk about Sasha.

I had been working through profiles when Sasha's appeared. She was quite open stating that she was a MtF transsexual, something I had never seen on a dating site and so I was immediately interested. My interest in TG women had grown in recent months as I had discovered snippets of videos that I could watch on a dial-up connection and found them hot. I have always enjoyed playing with cock but not the body it is attached to as men do nothing for me. But, the idea of a beautiful woman hiding away a thing of beauty and pleasure in her pants did appeal.

I clicked to indicate I would like to get to know Sasha more thinking I must be at the back of a very long queue and so was surprised a few days later when a message appeared. Sasha's reply was polite and asked me to send more information about myself. I did and she replied quicker. Soon we were messaging each other every few hours and then one evening it was every few minutes. I felt I must be doing something right and so asked her out on a date.

Our meeting point was a bar near where I work. I met Sasha after work and she appeared in a light blue dress and small black leather jacket. She looked gorgeous, better than in her photos, and walked very elegantly. I wanted to shout out that, "this is my date this evening everyone," as other internet based had usually gone sour at this point. I greeted her with a handshake and gently pulled her towards me meaning that we could kiss on the cheek and then sat down for a drink.

Sasha told me more about herself. She worked as a nurse and enjoyed her work. She liked shopping and clubbing but also enjoyed travelling. I asked her more and she told me about her various travels starting in the Philippines where she was from and then in Europe and finally in the UK. She was interesting and spoke in slow hushed tones with an accent to her English. Later she asked me more about herself and I told her about me.

The evening was lovely and we decided to call it a day after a couple of drinks. Out on the street in the darkness I gently slipped my arm around her and she reciprocated by pushing herself up next to me. When it was quiet I leaned in and kissed her, a kiss she responded to. We said goodbye shortly afterwards as we were travelling in different directions. I left feeling very elated but also desperate to see her naked as I wanted to savour the site of her slim body, gentle breasts and of course her cock. I was starting to get quite turned on thinking about fondling her, taking her cock in my mouth and even her fucking me.

I followed up the next day by texting to tell her I'd had a nice time and could we meet again soon. Sasha replied quickly saying the same and we agreed to meet for dinner. When I asked if she had a preference she said, "come to mine, I'll cook."

She had dressed stylishly again for our second date and wore an elegant dress. I had made an effort too and brought her some flowers and Champagne. Dinner was very nice as she had cooked a dish from the Philippines. Soon we settled down to finish the Champagne and we grew ever closer until we kissed. Our kisses were hungry as we both wanted each other. We explored each other's bodies and then she stood up and led me into the bedroom.

In the gloom she undressed removing her bra and allowing me to see the dark nipples against the tanned flesh of her breasts. She kept her pants on and it was too dark to see the curve of her penis. I undressed down to my boxer shorts and we climbed into bed together.

Her naked body was lovely to touch. Her skin was soft and warm and I enjoyed kissing her mouth and then moving down to caress and kiss her breasts. She moaned as I excited her teasing her nipples first between my fingers and then my tongue but I knew what I really wanted to see was further down.

My hands moved lower gently brushing her tummy and then further until I felt the hem of her pants. I stopped and waited to get a sign that I could continue. At this point she broke off and lay on her back, I started to gently feel the outside of her pants and could feel the curve of her now hardening penis. She moaned more loudly and then finally arched her back to pull her pants down. I felt her cock spring free and get harder in my hand. I gently started to wank her and then moved down to take it in my mouth. I had no experience of giving head and my attempts were probably pathetic. I did as best I could but broke off to continue with masturbating her. She enjoyed my hand sliding up and down her member and reciprocated by putting her own hand inside my boxer shorts and wanking my own cock. We continued kissing until she broke off saying she wanted to savour her climax later.

I didn't know what would happen next as I didn't know if she was a top or bottom (terminology I had yet to learn) and so followed her lead. "You would like to fuck me," she asked. I nodded slowly to say yes and so she moved down to fellate me and when she felt I was ready lubed herself up and presented her bottom for my entry. I was quite stunned at how skilfully she swiftly produced a bottle of lube from an unseen drawer, laid on her back pulling her legs up and then applied some to her bottom.

I marvelled at the sight in front of me. I had never had anal sex and so this was a first. I pressed my hard head against her opening but it wouldn't yield. I held the end and pressed again and still no joy. More pressure caused the dilation of her sphincter I needed and then I entered her, her slick sides aiding my entry. Finally I was in and could start fucking her.

I was probably not much good at the fuck as it was my first anal but I loved it. She had a tight bumhole and the pressure on my own cock was lovely. After entering her she had placed the soles of her feet on my shoulders. I loved looking at her face as I fucked her and soon, and without enough time to savour the experience, I felt my climax build and then release. I shot my cream deep inside her and she squealed as it must have filled up her bottom. Soon my cock was limp and I pulled it out of her.

She snuggled up next to me and we fell into a contented sleep. I woke up in the early morning and wanted more but knew she needed to sleep. In the morning we had more sex and then I left.

I never heard from her again. I tried phoning her and left messages but no replies ever came. Her profile was still active on the dating site but she wouldn't reply to me there either. I felt I had been used by her and to be honest I felt great about that.