More Lessons with Kelli Ch. 02

Writers Note: All I can say is that this chapter talks the start of some major changes in both of our lives. But as always, they have been good and fun. Keep the emails and comments coming.

I had thinking a lot over the past year about how much I enjoyed dressing up and going out as a woman. By this time I was spending Sundays and several nights a week at the house dressed, although those days, it was more causal than my going out clothes. I wore silicone fake breasts but I had also been thinking on how much fun it would be to have real ones. I have always been a boob, well, kinda of person. Big or small, that's what I always checked out first on a woman and would spend a lot time playing with them in bed. I hadn't said anything to Kelli about this, but once in while she would tease me about getting breasts, although she hadn't done it in a couple of months. A few weeks after my birthday party weekend, Kelli and I were in bed making love and afterwards, we were taking and playing a little. This time she playfully asked if I had thought some more about getting my own, as I played with her breasts.

I said to her, "Would it surprise you that I have been really thinking about it?

She smiled and replied, "Whatever you want is fine with me, but I think it would be nice."

"I know," I answered, "But there is the problem of what to do when I am over at the store."

Kelli asked, "How big are you thinking? Jenna's size?"

I laughed, Jenna is post-op transsexual friend of ours who has a set of double-D cups although they looked larger than that, and said, "No, not that big. But I am thinking a C or D cup would be right for my chest size," which is forty-four inches and not going to get any smaller, "But I would want to see what it would look like."

She said, "That is easy enough to do, but you should get your body hair taken care of first."

I had been shaving everything except my pubes since I had met her and I answered, "That would be okay with me."

From the look in Kelli's eyes, I could tell that she already had a plan of attack and after supper the next day, she made a front and side sketch of my chest. I haven't mentioned this before but she is a very good artist, although she says otherwise. She began taking hormones during her senior year of college and had spent a lot of time designing how she wanted her face and body to look like. I have seen those sketches and they are very close to what she looks like now. When she was done with mine, she took some measurements, looked up the sizes on a bra size chart, and then used some tracing paper to work up what I would look like with both sizes of implants.

She showed me both of them and for my chest, a C looked okay but I liked the D size better and I said, "But there still is the issue of me going out as a man."

Kelli replied, "A larger shirt with a sports bra would work the best, maybe with some extra padding underneath" and she added with that smile of hers, "But then you could start living as a woman full time."

I looked at her and answered, "I have been thinking about that also, but that will mean closing the store and finding something else to do with my life and I'm not sure that I'm ready for it."

With a smile she said, "I know, but it is something to think about, and it will be a lot of fun," and to be honest I knew that it was going happen at some point, especially with having to wear a bra every day.

She also took a couple of photos that evening and sent them to the surgeon that had done her work. A few days later he sent back the images that he had worked up and they matched what she had drawn. As I was thinking about this, I got my body and facial hair permanently removed. We both did some shopping and picked up some more women's casual clothes, blouses, slacks and skirts, for me and I changed into them as soon as I home from the store. I have to say, it is one thing to go to a restaurant or bar dressed as a woman, where the lighting isn't all that bright, but it's another thing entirely going to a grocery store or shopping mall. But I decided that I was going to do it and I had to get comfortable with being a woman full time.

All this happened over a month and one night as we were lying in bed I said to Kelli, "I have decided to get it done."

With a smile she asked, "What size did you pick?"

I answered, "The D-cup, seeing as how I already have a drawer full of bras in that size and I like how they look."

She kissed me and softly replied, "I will be with you every second."

"I know you will, " I said, "And besides, its not like this is something that can't be undone if it doesn't work out."

Kelli replied, "True. It will be a little rough at first, but once everything heals, you will really like it."

I laughed and said, "Well I'm leaving it up to you to make sure that they don't get carried away in there and give me the whole works!"

She laughed and we made our love for the evening. Kelli called her surgeon the next day and he had just had a cancellation and was able to do me in three weeks. She arranged for some vacation time at her office, while me being self-employed, all I had to do was turn out the lights and lock the door of the store. Soon we were on a plane out to the city where I was getting this done and the next day I was wheeled into the operating room. My surgery was on a Friday, I spent the night at the center, and then we headed to the hotel that we were staying at for the next week. I won't get too much into the details but I was in pretty sorry shape for the first couple of days. I have a high tolerance to pain, and don't like taking pain pills but this time, I needed them. The first time that I saw my new breasts without the bandages and support bra I thought, ugh, what a mess. I had looked all this up online ahead of time and Kelli had said the same about how I was going to look at the beginning, but it is different when you are the one standing in front of a mirror. We came home on Friday after a final checkup with the doctor. Kelli took two weeks off to care for me. She had done this, along with all of her other surgeries all by herself and after going through just this procedure, I marveled at how strong a person she really was and I loved her all the more for it.

The second week went by and I was starting to feel better but she insisted that I take another week off. I hadn't been inactive for three weeks like this since my late teens when I was in a motorcycle accident and I was seriously bored but orders were orders. The post surgery instructions had said no sex for a month, but at the end of the second week, Kelli very carefully got on top and slowly rode my cock until we both climaxed. In a way I was a little frustrated since I couldn't do all my usual lovemaking with her but at least it was something and she made love to me like that every other day until I was healed. I also had to sleep on my back so our side by side snuggling had to wait as well. That weekend was also supposed to be our monthly date night with Ann and Jenna, but Kelli called them and said that we were both sick with the flu. Ann wanted to come down the next weekend but Jenna worked weekends and only had one Saturday night off a month.

The next week I got back to my regular schedule at the store. Since it was late in the fall, I could get away with wearing heavy sweaters and had a few of them from when I weighed a lot more than I did now. I knew this was a temporary solution and I'm sure I got a few looks but nobody said anything. My lease on the store was up for renewal at the end of February and Kelli and I had already talked about my opening a new store in another town as a woman. As the weeks went on, my breasts started to assume a more natural shape and our lovemaking got back to normal. I was still a little tender but that was getting less and less as time went by. Our next date weekend with the girls went well. When Kelli talked to them about joining us in bed for my birthday weekend, she had said that it was only going to be a once a year thing. But that didn't stop her sister from trying to talk her into doing it again and neither of us had said anything to them about my getting breasts. Jenna came back to the house with us to have fun with Ann. We were in our bedroom with the door shut and I had just taken off my bra, but was still in my stockings and panties, when the door flew open and Ann walked in naked.

She asked, "Kelli, do you have an extra tube of lube? I forgot mine." and she stopped and looked at me. Her eyes opened wide and after a few seconds went by she yelled, "Holy shit! Jenna get in here quick!"

Kelli walked out of the bathroom still in her lingerie, holding a tube of lubricant, and Jenna came into our room also naked, and after seeing my new breasts said "Damn girl, you are looking good."

Ann added, "Flu my ass. You could have told me!"

Kelli replied, "Well we wanted to save it for the right time," as she tossed the lube to Ann and said, "Now back to your room you two and close the door."

Her sister being the brat that she was, stuck her tongue out at she left the room, and said, "Nice boobs! Before you know it, you will have a pussy and be getting screwed like the rest of us!"

We both laughed and finished getting out of our clothes and into our nightgowns. I turned on some soft and slow music, which we danced to before we got into the bed and we were only there a few minutes when there was a knock on our door.

Kelli did one of her eye rolls and asked, "Now what?"

The door opened and both of them walked in wearing strap-on dildo's that had to be twelve inches long.

Ann asked, "Are you sure you don't want to play with us? I have a really good hard-on tonight," and she wiggled her hips to shake the thing.

I said, "Back to your room ladies," and they walked out laughing and closed the door.

We laughed again for a while and Kelli said, "One of these days."

I replied, "And I am thinking sooner than later."

Kelli agreed and we went back to our lovemaking and in the morning we went down to the kitchen still in our nightgowns. She was making breakfast and I was sitting at the breakfast bar sipping my coffee.

I thought I heard someone behind me but before I could turn around, a pair of hands reached around, grabbed my breasts, pinched my nipples, and Ann said, "Nice boobies."

Kelli growled at her as I pulled her hands off of me and asked Ann, "How would you like somebody doing that to you?"

Ann was wearing one of her slinky short robes and she shook her breasts right in my face and replied, "Hell, if I had a dollar bill for every hand that has been my girls, I would need three dump trucks to haul them around."

Jenna was still there, as she didn't have to go to work until that evening. Since it was getting close to the holidays, the subject came up of how I was going to hide them when we went to visit Kelli's family. I told her about my heavy sweaters and sports bras but Ann wasn't so sure how that was going to work.

I said to Ann, "Well the worst that can happen is that your father will freak out on me."

Kelli replied, "I am sure that it be just fine," and the first night up at her parents went okay with no problems, I just didn't get into any close hugs.

The next morning Kelli's father had gone off someplace and we had breakfast with her mother like last year, but she did ask me about the sweater, seeing as how warm the house was.

I looked at Kelli and then said, "It's because I had a boob job," and I pulled the sweater tight against my chest.

She looked at me, then at Kelli who was smiling and replied, "I will never understand all of this, but if that is what makes you happy. Are you going to get the rest chopped off?"

I answered with a smile, "No, this is it."

Her mom who is a big lady, reached under her breasts, lifted them up and said, "I don't know for the life of me why you would want to drag a pair of these around," then she laughed and added, "Maybe I should talk to the doctor about getting a pecker!"

We laughed as well and Kelli said, "You know mom, they can do that."

Her mother laughed again and answered, "Your father would shit a turkey!" and the laughter continued for several minutes.

The rest of the visit was fun and I stayed in my man clothes, other than my bra and panties, the whole time. I gave her mother a big hug before we left and she smiled as our breasts touched. We took a couple of extra days off to stay at a big hotel on the way back and I walked in with a different suitcase than the one that I had used at her parent's house. I'm sure the desk clerk noticed that the older man who had checked in with his young wife had somehow been replaced by a classy looking older lady but I didn't stop to ask. The dress that I was wearing is pretty tight and I had on pantyhose instead of my usual stockings. My bra cups were thin and by this time, my breasts had some bounce to them. After supper at the hotel restaurant, we went to the club that was there and had a great time dancing the night away. We girl danced with each other, but there were plenty of guys both younger and older who wanted to work the floor with us and I had no problem getting up close during the slow dances. Of course we got hit on, Kelli's excuse was that she had her period and mine was that I just had surgery down there and it was no sex for a month. But that didn't stop the one jerk from offering me fifty dollars to give him a blowjob.

I looked at him and said, "I wouldn't give you a hand job for anything less than a grand," after which he called me a bitch and moved on to someone else.

But overall the night was fun and in the morning we went for a swim in the hotel's indoor pool, which I was doing for the first time as a woman. Kelli always wore modest one-piece suits and she had gotten one for me. The bottom part went down along my legs a little so that nothing would slip out and there was a short skirt on it as well. The top was open in the center a bit and showed off the sides of my breasts. But there weren't too many people in the pool at that time and we were able to pull it off. Of course we had a good laugh in the elevator on the way back to the room. We went sightseeing that afternoon, and after another great night of dancing, we headed home and got on with life.

A few weeks later and it was time again for our date night with Ann and Jenna, but the weather was going to be bad and we canceled it. Ann said that she would drive down before the storm hit, but being snowed in with her for a weekend just didn't seem like it was going to be a whole lot of fun. But the next month passed quickly and during this time, Jenna started dating a guy, whose name is Tim, and while she had told Kelli a little about him, she talked about him for a while when we were all at the club.

Jenna said, "This is the first guy that I have gone out with that actually wanted to date me before we got into bed. Tim is a really nice guy. He didn't even ask about sex until the third date, and if he hadn't, I was going to drag him back to the apartment and rape him!" which got a laugh from all of us. She went on, "When he did ask me, I did something that I have never done before and told him about me. I thought that I would scare him off but he was cool with it. He told me that when he was in college that there was a bunch of guys and girls that always partied together and he had sex with guys as well as girls, but after college he went back to just dating girls."

Of course Ann just had to ask, "How big is his cock?"

Jenna replied, "He is seven inches long, kind of skinny except for the head which is big, but the great thing is that he can get hard and cum three times a night and sometimes four without a lot of time in between. But he is very passionate and while we do get hot and heavy, most of the time it is slow and easy and really beautiful."

I asked her, "Does he know what you are up tonight?"

She answered, "Yes and he is okay with it. I told him that once a month I get together with some girlfriends to blow off some steam and afterwards I wind up in bed with one of them. I am thinking of asking if he wants to move in with me. I really like this guy."

The rest of the night was a lot of fun and the girls stayed over in their room. That week Jenna asked Tim to move in with her, which he did soon after and a couple of weeks later, she and Kelli were talking on the phone and I heard a lot more laughing and carrying on than usual.

Afterwards Kelli sat down next to me on the couch and said with a big smile, "Wait till you hear this."

I replied, "From that look, it must be something pretty good."

She laughed and answered, "Jenna said that last week she had done a bunch of laundry and Tim asked if he could help her fold it. So she gave him all of her lingerie, figuring that he would get a kick out of it. She said that he took a long time folding it very carefully and that she could see that he was really getting turned on. So just for fun, she got him a pair of panties, an A cup bra that matched and some stockings. Then one night she handed him the bag and told him that since he liked her underwear so much that he should have some of his own. He opened the bag, got this really weird look on his face, and she thought that he was going be mad at her, but he smiled and said it was neat. So he went and got changed into it and they had a great time and she's gotten him some more. She has been doing his hair and putting makeup on him as well."

"Must be something that they are putting in the water," I said with a laugh.

Ann wasn't coming to visit that month. She had gotten the weekends mixed up and had made plans to go away with one of the guys she dated, if you want to call it that. She had at least six or eight, I was always losing track of the exact number, and she loving referred to them as her stud farm.

But we were still going out with Jenna and I knew that something was up just from the way that Kelli was smiling as she replied, "I told her that it was okay to bring Tim along when we go out next weekend and to make sure that he was wearing a bra and panties."

I looked at her and asked, "So is he coming to play afterwards?"

Kelli asked me back, "She hasn't said anything to him and I wanted to ask you first, but would you be okay with that if it happened?"

I smiled and replied, "Might be fun."

She kissed me and said, "It could be a lot of fun but there is something that we want you to do," and she told me the plan.

I laughed and answered, "This is going to be wild. I just hope that Tim is as cool as Jenna says that he is."

"I think so," she replied, "And just think, maybe you will get to be a woman in bed."

I said with a smile, "And you get to have sex with another guy."

She looked at me, "But he never will be as good as you," and we kissed.

The next week I went over in my head what I was going to say to him. Kelli told me that it was okay to tell Tim about her and of course I was going to tell him about me. Saturday night we met up with them at the club and I had on a dress that was sexy, but not trashy. Neither Kelli nor I went for that kind of look. Tim was skinny, about my height and had light red hair that was parted in the center and long enough that he could have had it in a ponytail. He also had a diamond stud earring in his left ear. The night was fun, we did our usual dancing together and with other people at the club and I had one fast dance with Tim early on. Later the girls headed out together to dance and I noticed that he was pulling at something under the back of his shirt.

I asked, "First time out wearing a bra?"

His eyes got big and he replied, "Yes, I guess that Jenna told you."

I laughed and said, "You get used to it and in a place like this, nobody will notice unless it's a slow dance and she is rubbing your back."