Lessons with Kelli Ch. 02

Writers Note: This is the second chapter in the story of how I met and came to love a very special lady. There is one more installment after this one.

*

I usually shower at night and before I got in on Monday, I decided to shave off my body hair. I had never done this when I had been crossdressing before, but I figured why not give it a try. The hair on my arms and legs is pretty sparse but I have a decent patch on my chest. I have a beard trimmer for when I let that grow, so I used it to get the bulk of the hair off of my chest and under my arms, then I trimmed up around my pubes as well but didn't shave them completely off. I got into the shower for a lot of razor work on those areas and my legs. Tuesday night I didn't shower, instead I took one on Wednesday morning so I could touch things up with the razor. After I got to Kelli's house and had gotten changed into my lingerie, I called to her to come upstairs.

My back was to her when Kelli walked in and I said, "I have something to show you."

I turned to face her, and at first she looked like she didn't notice anything, but then she walked over and put her hand on my chest above the bra and said, "This is nice."

I lifted my arms to show her my bare armpits and said, "Legs too."

"Pubes?" she asked with a smile.

I replied, "Just a trim there."

She kissed me and said, "You look very lovely."

I put on the dress and Kelli did her thing with my hair and makeup. I guess you can tell that I was really getting into this and during supper she coached me on how to act more feminine.

Later as we were out sitting on the couch, Kelli turned to me and said, "I have something to ask you."

I replied, "Sure."

She drew in a breath and said, "I would like you to make love to me tonight."

It took me a few seconds to realize what she was asking. We had never discussed the subject of anal nor had we done any sort of ass play at all. I had thought that it would come up sooner or later but this caught me by surprise.

I answered, "I would enjoy that very much, but it will probably hurt the first time."

With a little laugh she replied, "I talked to an online friend about it and she suggested that I get a set of butt plugs and get myself ready for the main event," which I smiled at, "But if I am going to lose my cherry, I might as well do it the right way."

I said, "I will try to be gentle."

Kelli kissed me again and lay her cheek next to mine as she softly said, "I know you will.

We kissed again for a long while then we went to her bedroom. When we got there, she got a tube of lubricant out of the drawer on the nightstand, which also had a box of tissues on it. I got completely undressed, put on my nightgown, then I pulled down the covers and got in the bed. Kelli came back into the bedroom and she had on a very sheer white nightie. I could clearly see her breasts and cock and she also wasn't wearing panties. The other thing I noticed, which I verified with my hand after she lay down next to me, was that she had shaved her pubes off.

"You weren't the only one who decided to shave this week," she said, "I hope you don't mind."

I answered, "No, not at all."

After rolling on my side, we kissed and started the dance of love. We were no hurry as we lightly stroked each others cocks and once in a while we would suck each others breasts, then lean down for a few gentle sucks on the other person's cock. Then after one long kiss, I reached over, got the lube and a handful of tissues. I moved between her legs and I sucked on her some more as I applied some lube to my finger and gently pushed it into her ass. I repeated this a few times and then I covered my cock with the lube. I wiped my hand on a tissue, then moved forward, put my arms under her knees and lifted them up. She was looking at me the whole time as I got into position and made sure my cock was right on her asshole.

I asked her, "Are you ready?" and she nodded her head to say yes.

I slowly pushed in until the head of my cock was inside of her. From the look in her eyes I could see that it was hurting but she didn't say anything, so I kept slowly pushing until I was completely in. After waiting a bit, I started screwing her very slowly at first. She pulled my head down so we could kiss, and after a while, I started moving my cock with longer but still slow strokes. Kelli was breathing hard and I could tell that she was enjoying this.

We kissed some more and I quietly asked her, "Feel like a woman now?"

"Almost," she answered between breaths, "Almost."

I was close to cumming but I managed to hold it off. But after a little while longer, I started going faster, and as my climax hit, I pushed in hard and stayed tight.

"Oh my god," she said, "I feel you going. Oh that feels so good."

I gave a few more stokes to help empty my cock out and stopped as my cock started to deflate. After I slid it out and wiped it off with a tissue, I moved back so that her cock was right at my face and it didn't take long for her sperm to fill my mouth.

After moving back on top of her and a long kiss, I said, "I am going to wash up a little."

Kelli said, "Okay, hurry back."

I smiled and after a trip to the bathroom, was soon back in the bed lying next to her and once again we fell into a long kiss.

I said, "I hope it didn't hurt too bad."

She smiled and replied, "When you first went in it hurt a little, but afterwards, I am so surprised at how good it felt, especially when you came."

I answered, "A couple more times and it won't hurt at all."

"I can't wait," was her comment as we settled in for another long session of kissing and playing.

At some point we wound up in a side by side sixty-nine position. Both of us had climaxed so hard that it took a while of soft sucking before we got erect again but that was nice also and we lay like that for a while. After my cock was good and hard, I got her up on her knees. I moved behind her, lubed my cock again, got her ass at the right angle, and gently entered her.

She said, "That was a little easier this time."

I made slow and sweet love to her for a long time. Kelli leaned back a little and I cupped her breasts and kissed her neck as my cock traveled in and out. Finally I bent her back down and picked up the pace until my cum flooded into her ass.

She said, "That felt so great that I almost came myself that time."

I pulled out, flipped her over, and once more, took her cock into my waiting mouth, until her cum was flowing hard and fast. I washed up again and she was lying on her side with a big smile when I came back to the bed.

"Must feel good," I remarked as got in next to her.

Kelli smiled and said, "I never thought that it would feel like this. I am glad that I waited for the right guy to teach me." She stretched out and after rolling towards me, we kissed, then Kelli went into the bathroom. She was in there for a while and said when she got back to bed, "My tummy is a little funny after all of that."

I replied, "Yes, that does happen. The porn stars usually clean out with an enema first."

"I read that someplace," she answered, "and I am sure that you know how to give them."

I said, "Of course," and we both laughed.

The next morning I awoke to the delicious feeling of having my cock sucked. I moved around, and after getting close to her cock, joined in a nice sixty-nine until both of us came. She had gotten me a robe similar to the one that she wore and I put that on for breakfast. Afterwards we showered together and I headed off for another week. Despite the fact that she didn't have to work, Kelli did have a job at an accounting firm.

I had asked her about it and she said, "While I was in Chicago, for the first five months I didn't have a job while my surgeries healed and I was bored out of my mind. I spent a lot of time practicing being a woman, things like walking and talking, but still there is only so much of that that I could do in a day."

I asked, "Does anyone at the office know about you?"

Kelli replied, "Yes, I didn't lie on my application. The personnel manager, who is a very nice older lady, and the guy in charge, both know. I haven't had any trouble or comments, and the bathrooms are for both sexes, so that isn't a problem."

She had told me before that she was from New York originally and I asked her what brought her here.

With a laugh, she answered, "Because I knew that you were here, silly," and we both laughed. Kelli went on, "I knew someone back in college that was from this area and they had told me how nice it was. I got tired of Chicago after a year, I really didn't like living in the city, and decided to see what things were like here for a while. I lived in an apartment for six months before finding this house."

I answered, "Well I am glad that you did!"

During that next week, I did some thinking and decided that I wanted her to do me as well. I thought about it over the years, I've had a few small dildos and vibrators in there, but I was always afraid that I would run into someone with a huge cock. Call me a chicken or whatever you want, but with her cock being small, I figured for a first time that it would be okay.

So as we were sitting on the couch, I kissed her and said, "Tonight, I want you to make love to me."

Kelli's eyes opened wide and after a moment of silence asked, "Really?"

I answered, "Yes."

She replied, "I can't say that I haven't thought about it since last week, but I never imagined that you would ask."

"First time for everything," I said as we kissed.

I let her take the lead that night. Not that we usually didn't go to bed as equals, but she usually let me set the pace for our play. But this night I wanted her to take charge and told her so. Everything went fine, right up to the point when she got in between my legs and started pushing her cock at my asshole. She was too far back, so I told her to get very close. Kelli moved up so that her legs were touching my ass cheeks, she pressed her cock again at my asshole but as she leaned over, she went down too fast and before I knew it, her cock was buried completely in me.

She said, "Oh my god, I am so sorry, I didn't want to do that. Are you okay?"

My ass burned and stretched a little, but it wasn't too bad, so I said, "I am fine. Just go slow," which she did.

It started feeling good and I told her go faster, then after a few minutes she asked, "Do you want me to cum?"

I kissed her and replied, "You are in charge. You cum when you want to."

A few more minutes went by, then she picked up the pace and pushed in as far as she could go. I felt her cock throb, I knew that she was cumming deep inside of me, and that felt so nice.

"Wow," she said, "I didn't think I was going to stop cumming."

"It felt fantastic," I answered. She started to move back but I said, "Stay inside me for a while," which she did.

This was one of those moments to savor, strange as it may sound.

After a couple of minutes of passionate kissing, she moved back, and after wiping herself off, got on her back and said with a smile, "My turn!"

I made love to her for a while before leaving my load deep inside of her.

Afterwards as we were laying there, Kelli said, "I am so sorry about what happened. I can be such a klutz at times."

I replied, "That was okay. It really wasn't bad. Now if you were as thick as I am, I would have been screaming my head off," and we both laughed.

She got a very serious look on her face and said, "I just really hope that I didn't get you pregnant," and we both laughed again.

We made love to each other again that night, starting off doggie style and finishing on our backs. My ass was a little sore but not too bad. We snuggled up close and I woke up first that morning. I reached over and started stroking her cock, then as Kelli woke up, she reached back and started stroking mine.

After playing like that for bit, Kelli asked, "So what is your pleasure this morning?"

I answered, "I would love to have you cum in my mouth, but if you want to go someplace else, that is fine with me."

She laughed and answered, "Pittsburgh!" and I laughed as well. She rolled over to face me and softly said, "Whatever you want."

I pulled off her nightgown and she did the same with mine. Then after spending some time with those beautiful breasts, I moved down and took my time sucking her off. We changed positions and she gave me the same pleasure, then after breakfast and a shower, we said our good-byes. When we talked on the telephone on Friday, she asked if I wanted to come over Saturday night and stay until Sunday. I didn't have anything else to do, and well to be honest I really wanted to start spending more time with her so I said yes.

Kelli said, "That is great. I have something very special in mind."

I was curious but she didn't give me any clues. But I didn't have any reason not to trust her and I figured that it was going to be fun. She had gotten me a nice looking woman's suit, dark blue skirt and matching jacket, along with a semi-sheer off-white blouse and black stockings. My panties were light blue, the bra and slip were white. She fixed my hair up in a French braid with a clip to hold in place, and along with the earrings and necklace, she added a couple of gold bracelets to my wrist. I really looked good and she was dressed in a similar fashion.

She said after everything was done, "We, are going out for supper tonight."

A look of panic crossed my face as I said, "I am not real sure about that. What if I run into someone I know?"

Kelli said, 'Don't worry, this place is far enough away and it is a very private restaurant. You will have a lot of fun."

I wasn't really convinced, but I didn't want to disappoint her either so I agreed. She gave me a purse to carry, not that I had anything to put in there, but she had put some makeup, tissues, and a comb inside.

I said, "You forgot the Tampax."

"Silly me," she said with a smile.

The restaurant was a good hour away from where she lived. I had never heard of this place, but then I wasn't much for fancy dining either. The place had several rooms and they were fairly dark with a lamp at each table. The waitress, who was a tall girl with big boobs, knew Kelli, so I assumed that she had been there before. I was her aunt for the evening. I can't say that I wasn't self-conscious about doing this at the start, but the meal was good and after a while I was feeling pretty comfortable. That was, until it was time to leave and I had to make a bathroom visit. But Kelli went with me into the ladies room and fortunately there was no one else there at the time.

As we were driving back to the house, Kelli asked, "Now tell me honestly, was that so bad?"

I replied, "No, it wasn't. But I never thought that I would have the balls to go out to a place like that dressed like a woman."

She laughed and answered, "I really don't think anyone was worried about your balls, well maybe me, but," and we both laughed

I said, "I'm pretty sure the waitress could tell, but she was being discrete."

Kelli said, "She is a post-op transsexual."

I looked at her and replied, "Really? I never would have guessed."

She answered, "I met her on one of the transgendered boards on the Internet. She had her surgery done three years ago and says that she loves it. She hasn't had any problems at all."

"Wow," I said.

Kelli replied, "She is the one who told me about the place. I have been down there a few times before. She did ask me out on a date but I told her that I had a very mature and special lady friend."

I laughed and said, "Oh boy!"

We headed upstairs as soon as we got back to her house and spent a lot of time slowly undressing each other down to our slips and stockings. We were both very horny, but we still took our time. She made love to me first and it was fantastic. Ten minutes of pure pleasure as her cock moved in and out, her breasts cupped in my hands and our lips locked tightly. Then it was my turn and I returned the pleasure back to her. We spent the next hour or so in quiet but passionate love play before once again, joining our bodies in our slow and long dance of love. It was after midnight before we called it a night and we slept in late the next morning. That Sunday morning it was raining and well that is just perfect for spending the day in bed. She started off by sucking my cock, but after a few minutes, she wiped it down with lube and carefully lowered herself onto it. I have been ridden by plenty of women but this had to rank with the best of them. I am too heavy and my knees aren't the best, so I couldn't return the pleasure to her that way, so I just bent over and let her take me from behind. We showered, then after putting on nightgowns and panties, headed downstairs for some much needed coffee and food. She used a blow dryer on my hair and fixed up again since it had gotten messed up during the night.

Kelli said, "Next weekend, I am going to try and get some curl in your hair."

I replied, "Whatever you want is fine with me."

After breakfast, we spent a couple of lazy hours in bed before making love one final time to each other.

Wednesday night was fun as always. Being with her and especially in bed with her was great, no matter what we were doing.

That Saturday, I got there a little earlier so Kelli had time to work on my hair. She put some stuff on it and rolled it up in hot curlers. It wasn't what I considered fun but the results were worth it. When she handed me my purse before we left for the restaurant, I opened it and don't you know, there were a couple of Tampax in there. She did have a sense of humor that girl. Supper was nice and I felt comfortable enough to talk with our waitress, whose name was Jenna, a little more. I still had a hard time believing that she was once a man, there was nothing at all that could have given it away.

She asked, "I hope that you are taking good care of this girl," as she pointed to Kelli.

I answered, "I take very good care of her and she takes very good care of me."

Jenna smiled and replied, "So I have heard."

I looked over at Kelli, she just shrugged her shoulders and looked away with this funny little smile. I also decided to try a trip to the ladies room by myself. There was someone in one of the other stalls, but I waited until I was sure that she was gone before I got out. That night in bed, Kelli was in a really silly kind of mood.

While she was making love to me the first time, she would put her dick all the way in and say "In," then when she pulled almost all the way out, she would say "Out." This went on for a few minutes before she started giggling. Then at the end, as she went faster, I heard her say, "Oh, oh, oh," with each stroke, and a long ,"Yeah," as I felt her cum. The silliness continued while I was making love to her when she started singing, "Gonna make a baby, gonna make a baby, gonna make a baby, tonight, tonight."

I started laughing hard and so did she, and after I was done, I asked her what got her in such a goofy mood.

She said, "I had a great phone call with my younger sister today and I finally told her that I was seeing someone. She asked if it was guy or a gal, and I said, well she likes to wear bras and panties but she also has a beautiful cock. She asked how getting fucked for the first time was and I said I didn't get fucked, that I had the sweetest love made to me and it was wonderful. She said that the first time she took it in the butt, it hurt so bad that she was walking funny the next day."

I laughed and replied, "I have heard that before."

Kelli also laughed and said, "She told me that if it looks like eight inches, it is going to feel like ten once it is in there!"

"No argument with that here," I answered with another laugh.