Did I ask for this? by Martyn1981

I accompanied a gay friend to an LGBT club. I wasn’t sure what to expect. I was curious about what I’d see. I could see a trans lady near the bar. Maybe in her 20s. long straight dark hair. Maybe a wig. Nice face, pink lipstick, eye lash extensions. Her hair covering both sides of her face. She could hide behind that hair if she needed to. She wore a sleeveless black dress, tights and black high heels. She had long pink nails.I noticed she was now walking towards me. Did I look for too long?

I accompanied a gay friend to an LGBT club. I wasn’t sure what to expect. I was curious about what I’d see. It was busy. My friend was chatting to another guy. 3 of us together by the bar. I was leaning against it. I heard some of what my friend and the guy he was with were saying. The rest of the time I was people watching. Glancing around, checking out the clothes, hair, footwear, faces.

As expected it was a mixed crowd. There were a lot of men, very few women and quite a few trans people. Some looked like men in woman’s clothes and make up. Some looked prettier with feminine features, soft makeup and nice clothes.

I could see a trans lady near the bar. Maybe in her 20s. long straight dark hair. Maybe a wig. Nice face, pink lipstick, eye lash extensions. Her hair covering both sides of her face. She could hide behind that hair if she needed to. She wore a sleavless black dress, tights and black high heels. She had long pink nails.

She had breasts. Breasts you would notice. The dress was close enough to see the shape. She was very pretty.

I was about to check out more people across the room when I noticed she was now walking towards me. Did I look for too long? What would she say. Hopefully not much.

Hello she said softly.

Hey I replied.

Not sure what else to say as I looked back at her for a second.

She asked me over for a drink.

I wasn’t sure what to say. How to respond. How to say no. I just stood open mothed and silent.

I looked into her eyes, her face between long dark hair. I was looking at a young woman’s face. My mind knew different but my eyes saw woman.

Within a few moments we were sitting at a table with drinks. She had asked for Champagne cocktails.

We made small talk and I complemented her looks. It seemed the nice thing to do.

She had her hand on my shoulder as she looked at me. I wondered if anyone was watching us. I looked straight back at her not daring to look anywhere else. I kept glancing at her long lashes, pink lips and long nails.

She said I reminded her of who she used to be. She said I was similar to how she used to look. I am 6ft tall and very slim. I worked out so was toned but still very slim with thin arms. Its why I caught here eye she said.

In my mind she was half who she used to be and half a new woman. She was about the same height as me, very slim, slim long legs, slender arms, long hair extensions, she still had a cock and had breast implants.

She said as a trans person she always wanted to look good. I agreed with her that everything she had on was very nice. I said her stockings and heels were hot. She had me touch her stockings just below the dress line. They felt nice. Her hand was permanently on my leg as we spoke. 3 Champagne glasses later she had me saying how much I liked the look of high heels, stockings, skirts and dresses.

I was then invited back to see her full wardrobe and as she put it her many slutty heels. It was late and the club was much emptier and even the person I came with was no where to be seen.

The small room in her flat was a walk in wardrobe. Drawers full of panties, stockings, tights. Many dresses on hangers. A dresser table with 3 mirrors covered in all kinds of make up of so many colours. The room had several full length mirrors. I can spend a lot of time in here she said.

Let me put something else on for you. A fashion show and she guided me onto the stool in front of the dresser. She removed her dress revealing her top half. A lacy black bra. She removed the bra so and I could see her breasts. I liked how they looked. Very nice indeed. Nice cups. She removed her pants and out it came. Her big cock hanging there. My internal temperature rose as my eyes dashed between her breats, face, bottom and cock. She stood there in heels, stockings and nothing else. It was a striking look. A tallish slim womanly figure with cock hanging between her legs.

She changed her stockings for fishnet stockings slowly. I watched as she unrolled the old ones off each leg then rolled the new pair up her long legs. Her cock in full view every second. It was bigger than mine. She pulled her heels back on.

Then she held up another pair of fishnet stockings similar to what she had on. These are for you she said holding them out to me. I tried to laugh it off saying I couldn’t but she was having none of it. See how they feel on you. I stood open mouthed staring at a pair of fish nets.

She undressed me and sat me back in the stool. I was slightly ueasy to say the least when she pulled my pants down. I sat there naked slightly covering my self whilst looking up at her. She helped me into the pair of stockings. I looked down whilst she rolled them up from each ankle to my thighs. Then she pulled across a pair of high heels and slipped them on my feet before standing me up.

She held my hand while I stood there looking down thinking I might loose balance.

She enticed me to walk to the middle of room. Her left hand holding my right hand as we moved. She said I should cross one leg in front of the other. I crossed each leg as we walked. she did the same. She stopped us in front of the full length mirror. I saw 2 sets of long slim legs in fishnet stockings and high heels. Our high heels made our legs look soo long. Our cocks hung between our legs. Our top halves bare. My torso exposed as well as her breasts. I had a semi. I tried to hide any facial expression that would suggest this. We turned and walked the length of the room. Practicing how to walk in heels. We turned at the end of the room. This time don’t look down she said. I looked forward. A full length mirror was oposite. We walked forward, holding hands, strutting. I could see our hips sway side to side as we moved forward. We watched ourselves as we got closer to the mirror. She was smilling as she watched me.

How about another drink she asked.

We sat side by side on the stool. She crossed her legs, so I did the same. She poured each of us a glass of champagne. She held the glass with her left hand and stroked my back with her right hand. I held my glass with my right hand and put my left hand on her lower back. Then then kissed me on the cheek before quoffing half the glass. I laughed watching her gulp the Champagne. Our knees touching, our sides touching and she was stroking my lower back. She gave me a top up and we each commented on how we looked. She said I looked pretty. No one had ever called me pretty before!

I thought this was all nice and was beaming. I touched her whilst we drunk Champagne. That bottle won’t last long. I felt the texture of both her and my fishnets. I touched her body and felt her breats. We were both aroused. There was no hiding it. A glance down and we could see the arousal. I was fealing at ease.

She suggested I pull out another pair of stockings or panties from the bottom drawer for us to change into. She said I could choose for both of us. Classy or slutty. It was to be my choice.

I went down on to my knees going for the bottom drawer. She stood up behind me and pushed down on my shoulders so I was on all fours and she pressed her cock against my bottom. I froze for a moment not knowing what she would do. Then she lent over me and started kissing my neck. She pulled my head back and started kissing my mouth. I tasted Champagne. She was pressing the length of her hardening cock against my cheeks. My mind was racing as I felt her length press against me. I was hardening also.

Her body leaning over above me. She had my head pulled back by my short hair and we were both kissing. I liked her tongue in my mouth and she kissed me hard. She then leant back and I could see us in the full length mirror. I was on all fours and she was kneeling up behind me with her cock pressed against the middle of my cheeks.

I seen something in her hand. It was a condom. She pulled away from me and her cock sprang upright fully erect. She put the condom on. Leaning her weight down through her arms on my waist, she pressed the tip against my anus.

She moved her hands from my waist to my hips and pulled me back towards her. Did I ask for this?! I was frozen as I felt the tip of cock push into me. I looked at the full length mirror. I could see her looking down with a look of concentration. she only had one thing in mind. She pulled my hips back hard and I’m sure she was now inside me. I was now looking down towards the ground feeling very nervous. I dont think I’ll like this I thought. She yanked back on my hips again. Oh fuck I thought. My heart was pounding, my mouth wide open with no clue what to do. She pulled back again on my hips thrusting her self forward. I wasn’t sure how to feel. It wasn’t sore but I wouldn’t say it was nice. My anus was stretched by her cock. I couldn’t see the penetration being on all fours and I coudn’t judge how big she had got. It felt big enough.

She was gently rocking her hips back and forth. She ran the tips of her long nails over my skin. lightly scratching me. Rocking back and forth and scratching my skin. Her nails felt great.

However, I could feel my self wide open. When she rocked forward my anus felt like it was being pushed in. When she pulled back it was like my anus was being pulled out. There was no lube. No sliding in and out. My anus seemed to go backwards and forwards with each stroke.

She then started to increase the stroke length. She was looking down at her cock entering my ass. She pushed slowly all the way in I let out a gasp. The feeling was almost too much. I could feel her cock so deep in me. But I couldn’t say if it was 4 inches or 12 inches, it was all too much for me.