Sherry got fucked by the Shemale hairdresser Shemale Sex Stories
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Here she was, at the Beach Party downtown, and as she walked around with a friend of hers she wore a loose skirt which the wind was kicking all over the place. Theresa is her first name. We work together. She doesn’t know it but I have this huge, huge crush on her and I want to go out with her if she’ll say yes.
However, I’m the type of guy who is considered a nerd. I’m scared of asking a girl out and I’m scared of girls in general. I always have been but as I’ve grown up it hasn’t been a big problem. Still I’m a little scared of girls nonetheless.
When I saw her at that Beach Party downtown my eyes stayed affixed to her curvy thick body. She’s the prettiest girl I know, or so I think she is, and a guy I know who’s a friend of mine told me a couple ways to get her to go out with me.
“You could just ask her,” he told me. “That’s one way or you could be a little sneakier,” he said. I asked what he meant. “Write a note. Sneak over and put it into her mailbox and then sneak away. That’s the other way, alright?”
“I’m not going to do that!” That’s what I told him.
He shrugged his shoulders. It didn’t matter to him. They were simple suggestions. That’s all they were. She’s a sweet and quiet girl. That’s why I adored her so much because she’s sweet and quiet. I liked that about her.
He didn’t care. “It’s only a suggestion,” he said. “Or you could ask her out face to face.”
“Face to face,” I exclaimed! “Are you like nuts?”
“She’s just a girl. That’s all. She probably wonders about being asked out. Have you ever thought about that?” he came back.
The subject dropped. We left shortly after that. I thought about her all the way home and as I did I wanted to go out with her and be with her and heck, I wanted to hold her hand as well. God, to hold her hand well I don’t know for sure how it made me feel, but I do know that if I could I’d be in another world. He dropped me off at my place and once I got inside I simply sat around while I thought about her. And I thought about her figure, smile, and her personality too.
She makes me feel special all the time when I see her.
Anyway, at home later on I thought about something much heavier then that. I asked myself what if I did get to go out with her. What if we did start going out and after several days things started to progress, emotionally, and whatever else came with that? I wasn’t sure about that.
I mean what if she wanted to have sex or play around? Me, well I’m just a guy. I’m just a guy who has never had sexual relations with a woman before. I really didn’t know exactly how to do those sorts of things. I’ve never gone to second base and of course I’ve never been to third base either. So I’m asking myself how do I uhhh get there if that sort of stuff goes that far.
I went online of course. I looked all that stuff up. I read and I read and I researched it as much as I could. I learned and I learned about it as much as I was able to learn. By the time I was done I felt confident that if a relationship did come to that point that I’d be able to do the stuff a man should be able to do or at least I thought I could.
Anyway, here I was, at work, and I started to ask myself how should I proceed with this? Then I answered my own question. I’ll write her a note and secretly put it into her box. I wrote it and re-wrote it until I thought I liked it well enough. I printed it, once I was at ease with it, and folded it and put it in a blank envelope. I put her name on it leaving mine off it completely.
Once I got enough guts to do it, I stood up, took a deep breath of air, and tried to be mature about it and walk it down to the mailboxes. I found hers and slid it in. In essence it read something like this:
“Dear Theresa. I’ve liked you for a very long time. I’ve liked your personality a lot. You have a very sweet smile. I love that about you. I’m not sure what to say here but some day I’d love it if we could go out on a date and have a nice time together. I’m scared at this point and time to use my name so I’m signing it by putting ‘affectionately yours.’ I’m not sure what else to say. I’ll write again.”
I wanted to write her later on that day but I waited, and I waited, two whole agonizing days. Yes, they were agonizing alright because I wanted to sit down with her, and I wanted to be with her and talk to her and I wanted to know all there was to know about Theresa. In that two whole days I found I was falling in love with her.
That day I put the second note into her mailbox was one of the most terrific days of my life. She somehow found out it was me who put the note into her mailbox and as soon as she did I got a call.
“Hi,” she said. “You wrote the note? Really you did that for me?” she said.
My answer was what I thought a soft spoken answer. “Yes. You liked it, honestly?”
“Tim, I loved how it sounded. I’d love to go out with you. I really would to be honest with you. Uhhhhhh do you want to meet somewhere or would you like to pick me up or what?” she said in a voice which for me sounded supple and almost seductive like. It was my imagination which had me thinking that way of course.
She made my day. I told her seeing as I wanted to be a gentleman that I could pick her up. The very first thing I did was to stop at the car wash and clean my car out. I cleaned it up and spent an hour doing it thank God. Then I went home and showered, twice.
I headed out. I left early and got there early. She was ready. She looked marvelous. At least in my opinion she did and I made sure she knew she looked “marvelous” too. The look on her face, once I said she did, said a million words. I felt honored to be with a girl, as pretty as Theresa was, and to be said yes to once I got a date with her.
We went to dinner. It didn’t matter where we went but I took her to a nice place. She liked it a lot, thankfully. I spent a lot but I didn’t care. Dinner with Theresa, for me, was super. We talked and we talked and we talked almost about everything. No, not everything, but in truth we talked about a lot of stuff including work of course.
Then she surprised me once we decided to leave. “Would you care to come back to the house?” she asked.
Oh my God! Come back to her house, really? Does she mean that? Really, she means it? Oh my freaking God! “Uhhhhhh, I uhhh don’t know,” I said. “I’m uh not sure,” I replied.
And then she turned and looked at me. “Tim it isn’t like I’m going to do anything if that’s what you’re thinking. I’m only asking you back to the house. That’s all.”
I was soooo relieved she said that and I said, in relief, “Ohhhhhhh oh uh good,” as I took a deep breath of air and looked at her. She had on this smile. It was a sweet smile too. I loved it and I loved the overall look on her face as she smiled into my eyes. “Uhhh good, that’s uhhh good.”
“Why’s that?” she said as we came closer to her apartment.
“Ohhhhhhh no reason,” I lied as I shook my head.
“No really,” she asked. “Why is that?”
We pulled into the parking lot. I asked her where she wanted me to park. She told me, smiling as she did, and of course I smiled back as best I could. She could tell something was going on in my thoughts, right then and there.
“Come on up?” she asked.
“Uhhhhhh sure,” I replied.
We went up to her second floor apartment. It was a nice layout, I thought. It had more then my place did. Maybe it was because she is a girl and females always have nicer stuff then guys ever have. It didn’t matter. Her personality did it for me. She was the perfect hostess, I thought, and I felt comfy right away.
We sat and talked some more and I felt I could move into her apartment right away.
About an hour later I left, telling her I had a great night, and we hugged. I didn’t want to let go of that hug she gave me. I wanted to hold on to her body all night long. Theresa felt soft and huggable and soooo loveable to me that I easily could have told her how glorious it felt to hug her like we did.
We said goodbye, smiling at one another as we did.
“Hey, I had a wonderful time last night. Did you?” Theresa asked, interrupting me.
“Ohhh hey Theresa,” I said, surprisingly. I smiled and looked right at her. My smile grew. “I did too. Really, I did too.” I didn’t know what else to say. I was at a loss for words.
“Want to come back over tonight?” she said.
I was shocked at the offer. “Really, you mean it? You want to get together again?” I said.
“Ohhhhhhh sure,” she said. “I’d love it.” Her eyes were aglow with a sparkle I’d never seen before. They appeared lit up. I loved how her face appeared in the dim features of my office. Her body of course looked soooo appealing to me that it would have been easy to stand up, strip down, and lay down naked on a bed with her right there at work. “What time?” I asked.
“I’m getting off early,” she said. “I’m getting off at 3:30. Give me an hour after that and if you can get off early come on over. How’s that sound? I’d love to have you over!”
She’d love to have me over. She’d love to have me over. Spirits filled my heart. They filled me all over. And all I wanted was to be with her forever, I told myself. I want to be with you Theresa, forever and ever and ever. Okay, I know it. I’m going too far to fast.
But I got off even earlier then she did and instead of going home to shower I went right over to her place. I got there at 3:15 and waited. She got there at 3:45.
“You got off already?” she said but with a smile. “I uhhh was going to uhhh clean up a little. You know take a shower, change my clothes, and hope that you could come over too. But seeing as your uh here already maybe we uhhh could,” but she stopped. She didn’t say what she had on her mind.
However, that’s when it came to me. Was she going to invite me to take a shower with her? Was that what she was thinking? Ohhhhhhh my God, I thought. Oh my God. I’d love to see Theresa naked in the shower. I’d love to see all her soft, round, curvaceous nakedness in that shower I told myself.
“We can umm still do whatever it was you were thinking about doing,” I told her. “I mean if its on the up and up of course,” I added, trying to be honest, and clean as well.
Then she did it again. She smiled right at me and said “We can. You’re right. We could.”
And to clarify whatever it was she was getting at I asked “Uhhhhhh what do you mean?”
“I get the feeling that maybe you’re a little uhhh green at all this. By ‘green’ I mean you have never been naked with another woman before? Not that I’m real experienced but I have been,” and she paused a moment before going on to say “with a couple men before but I don’t get the impression that you’ve been with a woman. Have you?” she asked.
The moment of truth hit me.
She was smiling. I wasn’t. I had this blank, stupid look on my face. She was comfortable with it all. She knew she didn’t want me to be in a position which showed my lack of experience but she seemed comfortable with it all and eased me into doing what she was getting at.
“Would you care to join me in the shower, Tim?”
“I uh…I uh don’t know,” I told her. “In all honesty, I haven’t ever been with a woman before.” I was shaking my head and looking at her. She was smiling a soft smile. “I’d like to be but uhhh I’m not sure I’m uhhh ready to be.”
Then she said it. “Let’s do this. Let me turn it on. I can get undressed and you can watch me and as I do you can decide whether or not you’d like to join me in the shower. How’s that sound? I’m just going to let the water run down over me. That’s all.” But then she stared right into my eyes and her eyes said it all.
“Please join me,” her eyes said to me, I thought.
But as she got naked, all by herself, I stood there frozen, and I didn’t do a darn thing. I watched her unfold. I felt my body as it began to feel weirder and weirder as this young woman, my age, undressed a luscious, spectacular, and most energizing figure of all figures undress herself openly right in front of me.
She started to get in the shower. My eyes said it all. They were huge like my mouth was as I watched her get into that shower. I could not believe it. I think I already had a boner going at the moment but she, at that moment, did not close the curtain to the shower. She smiled as I watched her stand naked in the spraying water and allowed me to watch it all go on.
“Come on Tim,” she said, sounding sweet as hell as the water hit her luscious body. “Take off your clothes and come on in and join me, please?”
I was horny as hell but still unsure of myself. “Uhhh I don’t know,” I said.
“Please,” she said.
“Alright,” I said.
And her smile grew as she watched me unbutton my shirt, undo my pants, and finally take off my pants and rest of my clothes. Yeah, I had a hard on and yeah, my cock tingled crazily, but oh my freaking God did I want it to be “handled” in ways a woman loves to do a man’s cock only it wasn’t.
I stepped into her shower and she smiled more then she already was smiling. Both of us were naked. The water, hot as it was, felt good on us, and then she said out of nowhere “I’m going to tell you something nobody knows about me. I haven’t been with a man in over 4 years now. You’re the first guy I’ve been with. You know why?” I said no. “Because you’re sweet, you’re a really, really nice guy, and well I love really nice guys I guess. I’m lucky and that’s why. So I hope this doesn’t make me look like I’m a slut. I really don’t hope it does.”
By this point our bodies, and my cock, were straddled up against one another. I really didn’t know what to tell her. “It doesn’t. Trust me it doesn’t,” I said.
“You are a nice guy but that doesn’t mean were going to have sex or anything like that.”
“Uhhh were not?” I replied by mistake.
“Oh uhhh you wanted too?” she came back.
“Uh no not if you didn’t want to,” she said.
“Listen,” I said. “Personally, I’m uhhhhhh a virgin if you want to know the truth. I’ve never been with a girl in my life. And I don’t know why I’m telling you either,” I went on to say. “I’m just being me. I can’t tell you how much I like you. I love being with you no matter what. I love you, personally speaking, but I love your figure more then you would ever know, Theresa. I do. I really do. I love everything about you to be honest.”
She turned around and looked me in the eyes and as she did I saw them coming at me. Her lips hit mine and she kissed me but then all of a sudden I felt something else. As she kissed me I felt her tongue slide out of her mouth and into mine.
It was soooo explosive to feel that I could feel it all over my cock. My stomach burned. My fingers tingled. My body felt it all over the place. And as a result my cock got harder then ever. And she felt it too because it stuck out and poked her in the belly.
“I haven’t even had sex with a man in years either,” she said. “But a girl knows how to take care of that, sometimes. Not me mind you but some girls do. Maybe I’ll try tonight.”
That only made me hornier but it didn’t matter. I was there in that shower of hers with her and we were naked, together. I loved it. She seemed to too. Life was good. We’d made a connection that made me feel as if I was in another world. And she “loved” me.
We went and dried off and laid down together. I wanted her and the longer I laid with her the more I wanted her. Still nothing happened between us that night. Later that next morning I got up and kissed her on her lips and we hugged and I told her how good a time I had being with her.
The following Monday she came to my office and shut the door. She had that smile I adored on her cheeks. “Do you know what I finally did on Saturday?” she said. “I masturbated. I wish you were there with me but I masturbated and finally I orgasmed but Tim it was still a lot of fun even though you weren’t there.” And then she said “I do love being with you. Can we get together again? And soon?” she asked.
I said yes.
Lauryn
- 07.12.2022
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