Something New

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First time with transgendered woman.
1.3k words
4.06
33.1k
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I met Becky in a late night bar after a night of clubbing. She seemed a really striking girl and we got on very well. She is tall with shoulder length dank blonde hair and has a very smokey voice. However she had to tell me that she was transgendered with her clothes on I couldn't tell. I'm a straight guy so was a little surprised. Still she was very honest and I was more than a bit curious so carried on. The first night we just got to a bit a kissing in the bar and swapped numbers.

Over the next couple of days we chatted a few times on the phone and the talk got a bit erotic Becky seemed to know exactly what to say to get me aroused. After about a week she invited me to her place. She did seem to sense than my curiosity might desert me at any time but I felt comfortable enough with it.

She has a nice small apartment and we sat in the living with a glass of wine each. We chatted a little and Becky sat close to me so that I could feel the warmth of her body next to me. As the chat got more flirty we kissed a little and when I had finished my glass of wine Becky stood up and held out her hand. I stood up as well and she led me into the bedroom. I started to feel both nervous and aroused at the same time. We sat on the bed and kissed. Our tongues dancing with each other. As we kissed I could feel that I was getting an erection.

"Would you like me to undress?" Becky whispered in my ear and I nodded.

She was wearing a simple white blouse and a pencil skirt. As it was summer she was bare legged. Slowly she opened the zip on the dress and let it fall to the floor. She then carefully picked it up and placed it on a chair. She then carefully undid the buttons on the blouse and turned away from me when she took it off her shoulders and put it with the skirt on the chair. She was not wearing a bra but when she turned to face me she held one arm across her breasts before slowly moving it so that I could see her. She had small but firm breasts that looked natural and perfect nipples. Her waist is very small but her hips are are very feminine. She was still wearing a pair of panties but made no move to take them off I wasn't bothered by this as I still felt a little uncertain.

"What do you think?" She asked.

"Very nice." I replied.

She reached over and helped started to undo the buttons on my shirt. When I had taken it off I laid back on the bed and pulled her on top of me. Her body was warm against mine and her breasts felt very good pressed up against my bare chest. As we kissed Becky moved so that she was laying next to me on the bed and she let her hand wonder down to my waist. I had a very hard erection and Becky laid her hand on it feeling me through my trousers.

"I think someone is very happy to be here." She said with a smile.

She deftly undid my belt and opened my trousers I was straining to get out. Soon I was laying naked beside her with her hand firmly grasping my cock. She carefully massaged the tip with her long thumb nail before starting with some firm strokes she seemed to be able to sense when I was close to cumming and slowed down gently massaging my balls before starting to stoke me again. This time she just used her thumb and forefinger and gripped a lot tighter again brining me to the edge before backing off. Then she gripped me again this time stroking faster than before.

"I want you to cum for me." She said.

She stroked me faster until came with a huge shudder sending squirts of cum all over my chest and belly. It was the best hand job that I have ever experienced. After I calmed down a little Becky took some tissue from the nightstand cleaned off her hand and from me. She then went into the bathroom to flush the tissues. When she returned she stood at the end of the bed.

"Shall I take these off?" she asked looking down at her panties. "Yes." I replied.

Becky slid her panties down and threw them on the chair with the rest of her clothes. Her cock sprang up a little. Climbing back onto the bed next to me she started to stroke herself until she was fully hard I found this a huge turn on and started to get hard again myself. I leaned across and kissed her while resting my hand on hers to my surprise she gently withdrew her hand and I was holding her cock in my hand. It felt a bit off and my first instinct was to let go. But I slowly tightened my grip and started to stroke her. I'd never seen another persons erect cock before in the flesh much less held one. It felt very warm and very different to my own.

"Faster" Becky whispered.

I started to stoker her faster as I did I could hear her breath quicken a little.

"I want you to make me cum." She said.

I carried on stroking her and soon I felt her cock twitch in my hand then the warm liquid cum oozing down my fingers. I stopped stroking but kept holding her cock until I felt it was starting to go soft. As I let go Becky handed me a tissue. I cleaned my hand up as well what had gone on to her belly then went to the bathroom and flushed it. When I returned Becky was sitting on the end of the bed. As I walked towards her she stood up and kissed me before sitting down again. I sat next to her.

"Can I feel you inside of me?" Becky asked.

It took me a couple of seconds to work out what she meant. I'd not ever had anal sex before so I wasn't sure.

"Yes of course." I replied.

Becky told me to lie back on the bed I did so with my head propped up by the pillow. She then gently started to suck me. I could feel my cock getting harder in her mouth. After a while she got up on her knees and reached across me to the night stand to pick up a condom and a small bottle of lube. She deftly put the condom on me then sprayed it with some of the lube. This was an odd sensation. After she had worked the lube in a little Becky kneeled over me and kissed me.

"Just relax." She said.

She sat up and reached behind her taking my cock in her hand then she gently slid me into her. I was surprised how warm it was inside her it was also a lot tighter than I was used to. Becky started to slowly ride me and as she did I reached up and played with her breast. After a few minuets Becky leaned forward.

"Want to take charge?" She asked.

Before I could answer she gently took herself off of me I sat up and then got on my knees Becky was already on all fours. I gently pushed myself back inside her tight ass. Then I started to thrust in and out slowly.

"Let yourself go and cum deep inside me." Becky said.

I started to thrust faster and harder and soon I felt myself cumming hard.

Since then I have had shared a lot more experiences with Becky.

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AnonymousAnonymousover 8 years ago

I was single 31, I was about to buy my first apartment, Kristina, the real estate agent was showing me through. Older than me, I couldn't help but admire her round bottom in her tight skirt uniform. Black hair, olive skin, hosed legs and a great accent, Uruguayan I found out, what wasn't to like. Well what do you think, well I like it very much, but we will have to deal. Oh, she said I will work very hard to get this sale, good, not 385,000 but 285,00. Sorry, not that much, ok, best 345,000. no, too much. There was another agent listed as well for the same property. That agent said 345,00 as well. I rang her back, Ok, Kristina, 345,000 it is , the other agent is quoting the same, why would I go with you. She said I told you I work very hard for my sales. Lets meet tomorrow at the apartment, I will bring the contract, I hope you will sign with us. At 10.30 I arrived, she was there, the contract on the table. I said I work hard, well I am prepared to give you a 3 month service agreement. She looked at me, service, yes, where is the agreement, she said let me show you. She turned ,undid her skirt, dropping it to the ground, her sheer hosed bottom on display. She bent over a little, turned and said most men like anal, do you, did I, I said well, don't tell me you have never tried it, well yes, I have, good, turning ,her hands at my zipper, my cock straight out, I heard what all guys like to hear, oh, you are very big, stroking me, so thick. I must admit, I am big, not huge but a good 8 inches and thick. Her tongue flicked my cock, have we a deal, her mouth covered the head of my cock. What about your pussy, her head moved back and forward. she moved back, grabbed a tube and put 2 blobs on the head of my cock, she turned, lowered her hose to just below her thighs and knelt low on the bed. She grabbed my cock, placing it between her bottom, I felt warmth, opening as she pushed back, my cock slowly sliding in, tight,velvety, I pushed, ohh, that's as far as it goes, easy, there was still about an inch of my cock still not in her, as I moved back and forward.oh fuck, big, oh big, oh yes and then I pulled her back hard as I pushed. She screamed, my cock pushed through some barrier and I held still as the head of my cock was in a real tight place. I could feel the beat of her heart on my cock, She said oh im cumming and my cum was literally milked and squeezed out of me.I couldn't take it, I pulled back and fucked her as hard as I could, both collapsing on the bed. I stayed in her, flexing my cock, she squeezed her anal muscles hard, one of the best fucks I had ever had. We uncoupled, she lay against me, guiding my hand to her pussy. All I felt was a small clit, her cock, I didn't move my hand away. I signed the contract. The service agreement is still in effect 3 years after I had signed.

AnonymousAnonymousabout 10 years ago
Please add more emotio

This is a great start but it is sort of a 'then x happened, then y happened, then z happened' story. If you add a little more dialog or even internal dialog it will help smooth it out.

kriss4912kriss4912about 10 years ago
Suoer Story

Great story well written and told hope there is more

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