Old Friend, New Relationship-Part 1

I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We both attended regularly for almost a year, in which time several of us formed a sort of loose union. Among those in our circle of friends was Jane, another gal about our age who was trying to overcome abuse at the hands of her ex-husband. She was pretty strong, though, and in short order was back in control so it seemed to me.

But one by one, members dropped away as new people joined the group and created their own synergy. I never lost track of Karen, though. We would get together for dinner occasionally, exchange greeting cards, and just talk on the phone every once in a while. I never asked her about her love life and she never inquired about mine. She knew that I moved from one relationship to another while I never detected that she even dated.

The whole time, unbeknownst to a girlfriend I had at the time, I was dabbling in my hobby. I was a closet crossdresser, and without someone living with me fulltime, I had ample closet space. But I always yearned for that relationship in which I could be open about my desires and even indulge in my deepest fantasies of feminization. I was willing to settle for just a taste of things, but I never thought that I could trust any of my girlfriends.

I’m not sure when my desire to share my secret with someone started, but it never went away. Over the years, it would come and go, always coming back stronger than before. And increasingly, I thought that Karen was probably just the right person. She didn’t know anyone that I knew and her integrity was beyond reproach. Every time I called her and hung up without telling her, I felt like I’d let an opportunity slip by. I rationalized my silence by convincing myself that the topic was something best discussed in person. I needed to make another date with her, and I did.

I can’t remember ever being so nervous as I was that day. As soon as the date was made, in honor of what I hoped to share, I decided I’d be all dressed up—at least underneath. If I didn’t get up the nerve to tell her (a very distinct possibility), I would at least have the pleasure of going out feeling all feminine underneath my male clothes. I shaved. I lotioned. I painted my toenails. I selected a black, heavy garter belt, black panties and a pair of stockings that I’d been saving for Lord knows what. Before I set off, I opened a bottle of wine and had a large glass of the liquid courage.

After a pleasant dinner at a local Italian restaurant (and some more wine), we went back to her house for a little more conversation and, of course, some more wine. You might think that this is where the story takes a decidedly more interesting turn (as I’d hoped), but I was made to wait. When things were just right, I dropped the bomb. Not surprisingly, she handled the news well, saying basically that she respected whatever people did in the privacy of their own homes and that she would expect anyone to do the same for her. It was that latter comment that should have been a signal. Instead, I said my goodbyes and drove home, wondering about what might have been.

A couple days later, she called me back and told me that she had been thinking a lot about what I’d told her and that, the more she thought about it, the more it intrigued her. She said that if I was interested, she would like to see me fully dressed sometime. When she asked about what kind of outerwear I had, I told her that all I owned was a black leather skirt and a black blouse. I was more than a little surprised when she specified that my outfit had to be some combination of pink and white: shoes, hose, skirt, blouse and underthings. I thought that this was a rather odd request from someone new to my scene and secret, but I also felt like it was kind of an order that I was more than happy to try to comply with. We made a date for the following Saturday and I wasted no time in making an appointment with a local gal who specializes in makeovers for guys like me and then set about accumulating the new things that I would need. The short time frame meant that I couldn’t shop while hiding behind the anonymity of the internet. I had to go out and find my outfit. With some considerable discomfort, I ended up with a sheer white blouse, a pink miniskirt, and some pink, patent pumps with five inch heels, naturally. And of course I had the foundation garments. I opted for a very strict white corset with garters, white panties and white back-seemed stockings.

That Saturday I could barely contain my nerves as I set about preparing. After another close shave and application of false toenails (French tips), I set off to Judy’s place toting my outfit, false eyelashes & nails, brunette wig, jewelry, and purse along with anything that I thought I might need. At Karen’s request, I threw in a nightie. I hardly remember Judy’s makeover, but by the time I left trailing a lovely feminine scent courtesy of my makeup artist, I felt truly transformed for the first time.

I arrived at Karen’s exactly when she told me to and rang her doorbell. I guess I thought I’d be invited in and we would sit and sip wine while I told her about my history with women’s clothing. The best I could hope for was to show a curious Karen how I was dressed at which point she might be turned on and end up playing with me like a new toy. So I was surprised when she answered the door almost immediately. I couldn’t tell what she was wearing underneath her long leather coat, but there was something subtly different about her. She had a more imperial demeanor and, unless I missed my guess, she was more heavily made up than for our recent dinner. She brushed past me and indicated that I should join her in her car. When I asked where we were going, expressing that I didn’t think I was ready for a public appearance, she dismissed my objections with a wave of her hand toward the passenger’s side of the car. I obediently and nervously climbed in beside her. Once we got going, she said that she thought it was time I took my hobby to the next level and then she remained silent for the rest of the half hour trip.

Our first stop was a small jewelry store in a strip mall near her house. Against her objections, I dutifully followed her into the store. When the young man working the counter asked how he might help us, she told him that we were there for an ear-piercing. He invited her to sit at a counter towards the back of the store set up for just such a procedure, and she, of course, indicated to him that I was the one who'd be getting his ears pierced. Once atop the stool, the now nervous young man (since he'd discerned my rue gender) brought out a series of stud-style earrings that would be my first. "Those just won't do", said Karen. "We'd like some large hoops for our girl here". He tried to explain that saftey policy dictates use of studs for a "break-in" period, but the wave of a $20 bill by Karen made him forget all about "procedure".

In no time, and with scant little pain, I was walking out of the store sporting a large set of hoops above which there was an additional set of studs "just for good measure" according to Karen.

We resumed our drive and soon pulled up in front of a modest house in a nearby town. As we walked up the front sidewalk, the front door opened even before we reached the door. Clearly we were expected. We were greeted by a tall, broad-shouldered, heavily made-up woman wearing a skimpy maids’ outfit comprised of a pink satin dress, pink seemed stockings, white high heeled pumps, and topped by a frilly lace cap perched atop long, cascading red hair. Despite the fact that her breasts were undoubtedly hers, it seemed apparent that she had not been born with them. I knew at once that my hostess had spent at least part of her life as a man. I was instantly excited.

We were shown into the back of the house where I was surprised to be reunited with Jane, she of the old divorce support group days. Her face was about all that I recognized. The rest was made more difficult by the fact that her now more statuesque figure had been poured into a red latex dress that ended far enough above her knees to show off the lace tops of her black stockings. Normally I would have remarked on how much taller she was than I remember but five inch heels will do that for a woman—or a man for that matter. She greeted me with a European kiss-kiss and said that I looked great. I thanked her for the compliment at about the same time that the maid returned with three cosmopolitans which she deftly served in spite of her own towering heels.

Jane asked, more like demanded, that I sit oppositee her on the couch and catch her up on how I came to be sitting in her living room so dressed. Over the next two hours I gave her the unabridged version starting with my compulsion to set my hair in my mother’s rollers when I was home alone in high school and proceeding up through my decision to come clean with Karen who sat transfixed throughout the story. At the completion, Jane said that she understood my desires perhaps better than I did myself and that I’d finally found a home. If I was interested, she believed that, with the help of Karen and Ricki their maid, I might find fulfillment. I was encouraged to consider it and, if I was game, we could start that night. Without thinking too much, I managed to squeak out that I was very interested. With that, Jane got up and said that I needed to see more of the house.

With some difficulty, I made it down the stairs to the basement behind Jane and Karen, with Ricki dutifully bringing up the rear. We went down a short hallway that led to a door that necessitated two keys to unlock. Prior to entering, Jane explained that there were certain rules that applied to this room, the first being that anyone who owned or had ever owned a penis was required to wear a posture collar. The second, and most imporatnt rule according to Jane, was that everything that happened inside the room was of a voluntary nature--nothing would be forced upon anyone. It was made clear to me that my participation in whatever happened in this room would be within my personal bounds. I quickly agreed to the terms, the excitment mounting in my stomach and my little pussy. After having established a safe word that would put an immediate stop to any of the proceedings that I deemed too much, Ricki reappeared at once with a rather severe pink leather posture collar. Karen held up my hair all around as Jane fitted the collar around my neck and buckled it into place.

I smoothed my skirt to dissipate my nervous energy, an act that elicited chuckles from the other three. "I think he's going to be right at home here, Karen", mused Jane as I was led into a virtual feminization playground. The first thing I noticed was a gynecological exam table. Surrounding equipment made me think that real live gynecology had been performed there and later that year, I would find out how true that supposition was. All sorts of equipment that I’d previously only seen in trade publications soon came into view. But the thing that got my fullest attention was a beauty salon station complete with a make-up counter, shampoo bowl and hood dryer, and manicure and pedicure stations all arrayed around a majestic fuchsia-colored chair. Beyond that, mostly out of my comprehending, the walls were covered with a variety of feminine accroutrement including high heels, wigs, dresses, purses, hats and even a small collection of wedding dresses. It was a massive room tastefullt decorated yet crammed full of the essence of feminity. Of all of it, that beauty salon chair held my gaze the most. As it turned out, ever since that first glimce, I have spent many wonderful hours in that chair under the ministrations of Jane, its owner and very skilled operator.

At Jane’s suggestions, I removed my skirt and top, leaving me rather fully exposed to my hostess and her party. Jane recognized my discomfort and suggested that I have a seat at the vanity. In short order, I was seated at the delicate swivel chair. Considering my definite lack of need for a makeover at present, Jane and Karen thought it best to go right to Step 2 in my journey into feminization. I wasn't exactly sure what Step 2 was, but I didn't have to wait long. Given the choice, I opted to be blindfolded. After securing said blindfold, someone swiveled me around so that I was facing out away from the vanity table. It was time, they said, for me to get my first taste of a man's penis. I was told not to worry—that they would start me off with a realistic dildo.

Tentatively at first, I opened my mouth. It's true that I'd sucked on realistic dildos during my closet sessions in my house, this was a completely different story. Soon, I felt the tip of a VERY realsitic penis eased into my awaiting mouth. Whomever was manipulating it worked with me, never giving me more of the thing than I could handle. It had become clear by now that this was no dildo--it must have been something that Ricki had been hiding in her panties. She gently palced her hands on the top and back of my head and skillfully guided me through my first (the first of many) blowjob. It was an exquisite experience, notable for several details that I hadn't anticipated. The texture of Ricki's penis was almost indescribably smooth. The smell that was a combination of her perfume and precum made my head spin. The gentle bumping on my neck of the hoop earrings resulting from the back-and-forth motion of my head during the blowjob was a wonderful reminder of how much further down the road toward feminization I'd come in just the time since I'd pulled into Karen's driveway. I loved how Ricki's penis seemd to engorge an extra measure, further tightening the skin on his penis, making it larger and smoother as he neared climax. And of course, the taste of Ricki's juice, when it finally exploded into my mouth was wonderful. It all was unforgettable.

That night was the start of a whole new life for me--one that I had long dreamed about.