tagTranssexuals & CrossdressersLessons with Kelli Ch. 01

Lessons with Kelli Ch. 01


Writer note: This is the first of three chapters to this story and it really happened.

Sometimes you are the teacher and sometimes you are the student, but that is what makes life worth living.

Running a small junk and antiques store in a small town isn't the best way to get rich but I get by. I'm in my fifties, been living on my own for a while, and am a bit on the chubby side with long gray hair that is usually pulled back in a ponytail. I also offer guitar lessons and I first met Kelli when she came in to ask about them. She was a pretty girl of average height, with a slender build, shoulder length brown hair, and nicely dressed in a blouse, sweater and slacks. I guessed that she was in her twenties. We talked for a while about what she knew and what she expected from the lessons and I felt that I could help her. The only thing that she asked was that I do the lessons at her house, which wasn't what most people wanted, but she offered to pay me extra for the time to get there so I agreed. Wednesday evening was good for both of us, so it was set.

Kelli lived ten miles from me and while I drove through that area a lot, I was surprised to see that her house was one of the nicer ones in that town. She greeted me at the door dressed in a similar fashion as when we first met. I followed her into the living room and the lesson went well. Afterwards, she asked if I wanted a drink, so I said yes and we sat and talked for a while. She was very pleasant, although something about her did seem a little different to me. I didn't see anyone else in the house and commented to that effect. She said that she had just purchased it and was living alone. I thought that she must be doing well financially but I didn't pursue that any more.

We continued the lessons for a couple of weeks and always had a drink afterwards. Our conversations were always fun and I liked being around her. By then I was sure I had figured out what she was, but I hadn't said anything. During our talk after the third lesson I asked her if she had anyone special in her life.

Kelli answered, "No, not right now."

I said, "That's a shame seeing how attractive you are."

She blushed a little and replied, "Why thank you. But there are some things that you do not know about me."

I smiled and said, "I am guessing that you are a transsexual, pre-op or post-op."

Her eyes got real wide and her jaw dropped a little, then she answered, "Pre-op, but how did you know?"

With a laugh I said, "Don't get me wrong, other than a few little things, I really wouldn't have known. The only real clue is the shape of your hands, they don't taper like a woman's hand does."

She looked at them, rolled her eyes, and also with a laugh replied, "Well that's something that can't be fixed. Don't you feel uncomfortable around me now? A lot of guys are."

I answered, "Not at all. A few years ago, I got into cross-dressing. I never went anywhere, but I had lingerie, stockings and a few skirts and blouses. I lost interest in it and got rid of all that stuff last year."

Kelli asked, "Are you bisexual?"

"Bi-curious," I said, "I've never been with another guy. I have looked around over the years but never met anyone that I felt comfortable enough. At the time I was crossdressing I was hoping to meet someone similar but never did."

She replied, "This will come as a surprise to you, but I have never been with a man. Everyone assumes that I am bisexual, but honestly I have never really thought of myself that way. I have wondered what it will be like once I get the last operation, to be with a man, but most of the guys I meet know now, even though they don't know what I really am, are so pushy and they scare me."

I answered, "That is what I ran into. The few that I talked with that sounded like bisexual virgins, never got past the first couple of emails, and the others I could tell that they were just looking for a fresh ass to use as a target. If it ever happens, I don't want to get into that right away. I want something with some real passion and I do want to try oral, and if I start it, I will finish it. And hopefully whoever I am with will feel the same."

Kelli looked away from me for a few seconds, I could tell she was thinking deeply, then she turned back facing me and said, "Tell me honestly, if I asked you to kiss me, would you?"

It was my turn to pause, but then I replied, "Yes I would."

She set her glass on the coffee table and got up from the chair that she was sitting on. I stood up as well. Kelli walked over to me, got real close, put her arms around my neck, closed her eyes and slightly opened her lips. I wrapped my arms around her back and my lips met her lips. The kiss was soft and slow at first but soon I felt her tongue gently probing and I extended mine to meet it. The kiss got very passionate and I thought, here I am, locking lips and tongue with another man, but it didn't really feel like that. My cock was hard, I couldn't really tell if her cock was but she was so close to me that I was sure that she could feel mine through my pants. We were both breathing heavy and the kiss went on for at least five minutes. After it ended, she looked me right in the eyes for a few seconds before pulling me into a cheek by cheek hug.

In a very soft voice, she asked, "Would you like to come up to my bedroom?"

"I would like that very much," I replied.

Kelli answered, "Okay, but I have to warn you about a couple of things. I have been on the hormones a while and well some times my erections aren't the best. Also, I'm not very big."

I moved my head back to look at her and said, "This is one of those times in life where size really doesn't matter," and we both laughed. "As for the other thing, I guess there is only one way to find out."

She looked deeply into my eyes again before pressing her lips against mine to start another long kiss. Then she went and locked the front door, after which she came back, took my hand and led me up the stairs to her bedroom. Like the rest of the house, it was nicely done in a feminine style with a queen sized bed in the center.

We kissed again, then Kelli said, "Why don't you get undressed while I get changed."

"Okay," I answered as she walked over to one of the dressers, opened one of the drawers and pulled something pink out. There were candles on the nightstands and dresser, and as she headed to the bathroom I asked, "Should I light the candles?"

"That would be lovely," she answered as she closed the door.

I went around, lit the candles and turned out the room lights. I got undressed and after pulling down the bedcover and top sheet, I lay down on the bed.

She called out from the bathroom, "Are you ready?"

I answered, "Yes I am."

Kelli said, "Close your eyes and don't open them until I tell you to."

"Okay," I replied as I closed my eyes.

A few seconds passed, then I felt the bed move a little as she got on and moved next to me.

She kissed me on the lips and said, "Open your eyes."

The first thing I saw was her face of course, but then I looked down at the short and sheer, pink nightgown she had on. I could clearly see her breasts and areola. She also had one a matching pair of panties but the fabric was still sheer enough to make out the line of her pubic hair.

I said, "You are very beautiful."

"Thank you," she said as our lips met again.

During the kiss I started moving my hand up and down her back, pausing it to gently rub her ass cheek before moving it back up again. She started doing the same with her hand. After a little I moved my hand under the nightie and after a few minutes, gently started playing with her breast. I had never been with a woman that had implants but this felt very soft, almost like she didn't have any.

We broke the kiss and I said, "This feels very real."

She laughed and replied, "They grew to a B size on just with the hormones. I didn't want a huge set of boobs so I only had them make me one size larger."

I lifted up the nightgown for a better view. Her nipples were small but still larger than mine and her areola were puffy and stood out from her breast. I leaned down and after a few licks, I started sucking on her nipple. I heard her moan a little from passion as I licked and sucked. My hand went back to her ass cheek, which I rubbed and squeezed. She was doing the same to my ass and when I was done sucking, we kissed for a while. Kelli did the same thing to my breasts. I'm not very sensitive there but it still felt nice. We kissed again and this time I started slowing moving my hand down her stomach. I slid it under the waistband of her panties, which weren't real tight, and pushed in until I got to her pubic hair. Her hand moved down to mine and we played with each other pubes for a little while, then I slid my hand down to her cock. It wasn't big just as she had said and was semi-soft, but as I started to play with it, she got hard. She was as thick as my thumb and five inches in length, but it felt nice to touch. Her hand was around mine and she played very softly with it.

"That is nice," she said, in between kisses.

"You feel nice as well," I replied.

I'm six inches long, which is average, but I am thick, and her hand felt so good as she explored me. I was being gentle with her as well, but I could tell that she was getting very worked up.

At one point she said, "Slow down a little, it's been a very long time for me."

I thought for a second and replied, "I guess then it is time to fix that problem."

We kissed for a little, then I slowly kissed and licked my way down her chest and stomach. I moved between her legs which she parted and rested her feet on the bed. I stroked her cock and balls through the soft fabric of her panties, then I pulled the leg elastic up and over them. I moved in close and took a good look at the first cock that I was going to suck.

Kelli asked, "Is there something wrong with me?"

I laughed and answered, "No, not at all. I'm just savoring the moment a little. Don't tell me when you are going to cum, just let it happen."

"Okay," she said as I stretched out so that her cock was right at my lips.

I kissed it a few times, and then licked up and down the shaft. She started moaning a little, which increased as I opened my mouth and took her inside. It felt great, I had imagined this many times but this was far better than I could have ever fantasized about. Pressing my tongue up against her cock I very slowly slid my head up and down. I could tell she was trying to hold back and I could taste the little shots of precum with each stroke. I picked up the pace and pressed my tongue even tighter and with a groan from her, the first long and hard shot of her cum flew into my mouth. This was followed by three equally hard spurts that I had to swallow a couple of times to get it all down. I know I shoot a big load but it was nothing compared to the volume that she let loose with. I had tasted my own sperm before but her cum tasted very nice. She started getting soft almost right away, but I kept sucking for a while, then finished off by licking her balls. I moved back up the bed along side of her and she turned to face me.

I said, "That was great."

She said with a smile, "You should have been on my end of it," and laughed.

I moved in to kiss her but she seemed a little hesitant and I said, "Don't worry, you won't get pregnant."

Kelli laughed and replied, "I guess I am being silly aren't I," and kissed me long and deep.

My cock had softened a little but she reached down, and after a few seconds it got hard again.

She said, "I guess it's my turn. Let me know if I am doing this wrong."

I smiled and answered, "Well I am sure you will know if you do it right," and she laughed.

She moved down between my legs and resumed stroking my cock with her hand. I always leak a lot of pre-cum and she leaned down and licked at it to get taste. Then she took the head in her mouth and licked around that for a while.

Kelli stopped for a second and said, "Here goes nothing," as she took about half of my cock in her mouth.

At first she was going slow, moving her head up and down, but she started going faster and I felt her tongue moving against it. This felt really great and it had been a while for me as well, other than the occasional whack off session, but that's a poor substitute for the real thing. Her one hand was cupping my balls and her other was around my cock which she started moving up to meet her lips. I got very close and held back as long as I could but she moved faster and that was all it took. I came hard and I could hear her breathing heavy as I did.

She kept going for while after I finished, then she looked up at me and said, "Wow."

With a laugh I replied, "I agree."

After she got back alongside of me and we kissed, she asked, "Tell me honestly, what did you like best about this?"

I answered, "Well I don't think I will be giving up eating pussy anytime soon," which got a laugh out of her, "But I am really looking forward to the next time you cum in my mouth and I really like kissing you. I don't know why, but I do."

Kelli asked, "Really?" and then with a smile added, "I really liked when you came as well. This wasn't at all what I had expected, well the cumming part was, but I didn't think that I would like it this much and well, this really felt like making love and you are a great kisser."

I replied, "Yes, it really special. This was what I was hoping for, doing it the first time, but I never thought it happen."

She said, "Yes, me too."

We kissed again and lay there for about thirty minutes just talking and kissing. Somewhere during that, our hands went back to each others cock and we lightly stroked and played.

At one point she said, "I guess I really didn't need the panties."

I replied, "They are not in the way and they feel really sexy next to you."

We were both semi-hard by then and I leaned down and started sucking her again. We maneuvered into a side by side sixty-nine position and lay there lightly sucking and kissing and playing with each others balls for a long time.

Kelli said, "I don't know if I can go again."

I could have cum again with a little persuasion, but I wasn't in a big hurry, so I switched around so that I was between her legs again. I took her in my mouth and started sucking. She got fully erect and I sucked faster and eventually she let fly with another big load of her sperm. I swallowed most of it but kept the last bit in my mouth for a while as I gently finished my sucking. It tasted really good, at least I thought so.

We changed positions and kissed. Her eyes got big when she realized what I had done but she just smiled. She took her time with me but when I came and she sucked until every drop of my seed had flowed into her mouth. When we kissed afterwards, I discovered that she had done the same thing with my sperm, but that was okay. We lay there kissing for a while and then it was time for me to leave. She went to her closet and put on long ivory colored silk robe. After I was dressed, we headed back downstairs, where I got my guitar.

At the door we kissed, and then she asked, "Same time next week?"

I smiled and replied, "I wouldn't miss it for the world," and after one more kiss I left.

The next week was pretty much a repeat of the first one. I never would have thought that I would be so looking forward to sucking a cock, but I really was and spending time with her was great also. It is strange how these things happen but I was already getting some strong some feelings for her.

On the way up the stairs she said, "I picked up something for you, I don't know if you want to wear it or not but either way is fine with me."

As we walked into the room, laid out on the bed, was a lavender colored woman's nightgown trimmed in off white lace and a matching pair of panties.

I replied, "These are very lovely and yes, I will wear them."

After another kiss, Kelli headed into the bathroom and I got undressed. The panties were a little loose but they felt so nice on my cock and balls. The nightgown came down to my knees. I felt kind of sexy in that strange way that men do when wearing women's clothing. The sex was more passionate than the first time and it was a lot of fun. I did notice that her erection was better than the week before and she stayed hard for a while after cumming.

I said something about it and she said with a smile, "I had a doctor's appointment last Friday and I asked him to give me a little something to help with it. I'm sure that you don't mind."

With a laugh I replied, "Not at all."

We talked as we lay there in bed and she told me about why she decided to change her sex.

Kelli said, "I never was much of a guy growing up. I sucked at sports and was more interested in art and the theater, even from an early age. I even got teased because my voice sounded like a girl's voice, even after puberty. I have two sisters, one three years older than me, and one who is a year younger. I always envied their clothes and then as they got older, their lingerie and makeup. And yes, I used to sneak in their room and try some of their clothes on when they weren't around."

We both laughed and I asked, "Did you ever get caught?"

With a roll of her eyes she answered, "Almost a few times," and she went on, "I tried to pretend I was normal, I dated girls in high school and college, even had sex with a few of them but it just never seemed right to me. I decided during my junior year of college that I wanted to become a woman. I did my research and started on the hormones my senior year. My family has a lot of money and I have a trust fund that was left to me by my grandmother. After I graduated, I moved to Chicago and started changing my life. I went on a diet, exercised to slim down, found a plastic surgeon, and started having the work done. When I showed up at home for Christmas that year, it was as a woman."

I said, "And how did that go over?"

Her face got serious, "My father went ballistic and he still barely talks to me. My mother was upset but she has accepted it and I talk to her a few times a week. My older sister, well she took my father's view for a while but she's been talking to me lately. My younger sister thought it was neat. We went clothes and lingerie shopping together and she even offered to get me a date."

I laughed and replied, "Well I guess all in all it wasn't too bad."

Kelli said, "The hardest part was getting them to understand that I wasn't doing this because I was queer. It was just who I felt I should be."

I asked, "And do you feel queer now?" as I reached down and stroked her cock.

She replied, "Do you?" as she reached down to mine.

I answered, "No. I guess I should, but this just feels so right."

She kissed me and said, "Yes, so very, very, right."

We started talking on the phone every day and Kelli had asked if I would come early on Wednesday for supper. When I got there, she told me to go up to the bedroom right away and get changed. On the bed was a complete set of woman's clothes. Bra, panties, garter belt and stockings, a full slip, dress, and shoes, which were all in my size.

She called up, "Do you like them?"

I answered, "Very nice, thank you."

She replied, "Let me when you are dressed."

Which I did and she came upstairs. She painted my nails and after fixing my hair into a bun, she applied makeup to my face. The finishing touches were a necklace and a pair of screw post earrings that were long and matched the necklace. I looked at myself in a full-length mirror and had to admit, I did look like a well-dressed older woman.

Supper was nice and later when we went upstairs, I changed into another nightgown that she had gotten for me. We had a lot of fun that night and we both took our time as we sucked and played, but there was some more that just the sex. Deep down inside I feelings for her, that should have seemed strange considering what she was, but they didn't.

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