Dressed So Ch. 05: Tess' Friend

I decided without checking with Gloria that we were going to follow this hunk to the end of

Island if necessary. I was so randy with anticipation; his golden hair, light beard, tight cheeks, wow. I hadn't ever seen such a beauty, and I stopped thinking.

Anyway, the short story is we hooked up once at his party; turns out it was his old man's party. The cutie pulled me into a room and we sucked and fucked each other, then all hell broke lose. His sugar daddy burst into the bedroom and pulled us apart, beating first Clarence then me with a belt. I lost my falsies and bra but was somehow able to escape further wrath by simply running, heels in hand, down the beach. I'd forgotten about Gloria. Her abuse was worse than mine; four guys had fucked her repeatedly and left her in the basement soiled and beaten. She awoke the next morning alone and crawled back to our small rented room. We never spoke about that night again and stopped seeing each other shortly thereafter.

So on Saturday I allowed hours to prepare for Charles. I'd placed a good deal of hope that this may lead to something special and possibly sexual. I needed a real cock in me, soon, but I recognized my anxiousness could spell doom and I re-focused on selecting my outfit. The weather would be mild for early May and therefore I could wear a dress and have a sweater along if it became too cool. That would provide me a bit of freedom; the red dress would say too strongly I was his, the lbd too sexy due to its length. Shoot I had four black dresses, all a bit too much for a first meeting. I was eyeing the black skirt and a soft cotton blouse. The skirt would look good if I worn sheer nude stockings but Pantyhose would more conservative. I found my newest set and considered the heels. I had recently bought a nice camel colored pair but were they too tall at 4 ¼" inches. Charles was tall, 6'-3" or so his profile said. I went to the Mac to confirm, so these heels would say I was confident and sexy. But what ivory or white lingerie set? I opened the drawer and reviewed the nine different sets. The blouse had a modest plunge so the lacy ivory bra seemed just right. I reached to my breasts to remind myself of how I'd changed since the Princeton fiasco. I had to pray Charles wasn't that type. It was several weeks after that attack before I'd been able to take a thin dildo into my pussy. But maybe I should be a bit more discreet; the soft cup Victoria's Secret set would be better. I would need a simple short slip and I grabbed the first ivory one atop the collection in the lower drawer.

My outfit was arranged and ready, now I need to bathe and pamper my body. I decided to relieve some stress before hand and after my ablutions I went to the club chair with my vibrator. Positioning my legs over the sides of the chair I moistened the head of the toy. My bottom easily allowed penetration. My favorite toy had the look and feel of a real cock. I lubed the shaft and held the bulging end while slowly running the tip along my perineum. As I slip the toy inside my boi pussy I gasped, enjoying the fullness. Imagining a new lover my mind brought my body along and within a few moments I was peaking. I cupped my hand and caught my juice. Now relieved I now focused on dressing just so.

So Charles agreed to a simple date, I think to confirm his impressions. I was a Lady and would allow him to look as I studied his contemplation. I wondered if I was I ready for a relationship, ready to share my inner self as well as all of my secrets? Was he the right kind of man, could he keep me sated? My sexuality was paramount; I needed to be fucked many times a week. My toys were used daily and on weekends multiple times a night. I'd sleep with a cock inside my pussy at least once a week, so I knew I needed a lot of sex or I wouldn't be happy. How does one confirm this scale of sexuality without testing the waters? I found myself dreaming of his cock and his body atop me. I smiled coyly, and figured that was a good sign.

While stepping from the shower I looked to the left and saw my image in the door mounted mirror, the towel concealing my shrunken clitty. I looked carefully at the very womanly form that was me. My friends had always been clear, 'you're a beautiful crossdresser Patrick'. And now I was a woman, not a part-time girl, with full high breasts and a narrow waist. I was transfixed for a moment realizing where I been just 24 months ago.

Back in college in Chicago several of the 'girls' pushed me to consider a sex change but I loved my small penis. One summer I'd had an internship with a Fashion House. I met several other boys who were quite beautiful when dressed as women. We spent that summer together sharing our issues and dealing with the conflicts. Two of the group had already transitioned, Tess was a local girl who had turned twenty a few months earlier and had never thought of not being passable, and Susan was from a Midwest farm. Though Susan had a very feminine face and only a tiny Adam's apple she was being torn apart by the conflict with her body and sexuality. I considered both of these 'girls' as more sexy and gorgeous than myself, especially Tess. She made several passes but I knew I didn't want that kind of relationship. I realized about this time that I could become a good-looking young woman, and possibly I could live a life as such. Maybe I could find a man to love what I was without trying to 'revise' my groin. It was more than my wide hips and thick, longish hair and soft voice that help me begin to see myself as a woman. These boys who dressed had an impact on my thinking, on how I considered my body and my sexual feelings.

When I was younger I'd had only one sexual encounter, with a girl near my age, but she'd treated me to her pussy without allowing me to enter her. Our sex play began and ended with our mouths and tongues.

"Patrick you are so soft and beautiful. I love that you take such good care of your hair and nails. No gross hairy boy will ever be allowed access to my pussy. Lick me again sweetie."

At eighteen I was still living as a boy but had allowed my hair to grow even longer, and I wore genderless outfits and even heels and make-up regularly. The girls worked for weeks over the summer to get me to consider using hormones but I'd resisted. I wanted to be a natural girl, I wanted to be liked by boys but not as a femme'. After an interlude on the Pier with an unsuspecting tall dark hunk I agreed. I wasn't prepared for a man to want me so strongly. His kisses and his hands were touching me. I took his cock in my mouth and quickly brought him off, my lips unable to contain his eruption.

The sexplay I'd had that summer was with a couple of the dressed boys, their bodies slim and smooth. But this Latin man I'd met late one June night was muscled and hairy, his phallus too large for me to consider taking into my body. I'd been penetrated many times but the mini dicks of the femme's I slept with couldn't match this man's meaty cock. Afterward I considered what lay ahead and I knew I wanted to be loved and fucked by a man, daily if possible. I settled on my plan and with the help of Tess and others made the decision that hormones would change my life.

I tried several combinations but Tess insisted; she brought me to her doctor. This MD put me on a hormone therapy and of course I never looked back. My skin started to clear and soften and my breasts started to bud and my fat redistributed. After returning from the summer away I was certain I would never be a boy again. The nagging question then was 'am I a gay male or a heterosexual transfemme?' but I knew I wasn't a boy. I felt comfortable with my gender decision. I liked men, I like their cocks, I didn't want a pussy between my legs. In fact I liked my small clitty, reduced by the therapy.

Yesterday I'd receive an E-Mail update from my friend Tess. She seems to have found a partner, but her search has been a difficult one. Tess had transitioned before the age of eighteen and had become a serious lipstick lesbian, heels, full make-up and great clothes. Finding a woman, no, not just a woman but a beautiful woman, to love her was her primary goal. So something noteworthy had to have occurred. I flashed off a quick note of my personal situation, the legal ID changes, the job, and now Charles' interest. Tess responded immediately, she was coming to the City sometime within the next three weeks.

Her note said, "Take it slow Girl, and please be careful. I love you Lu." She'd become my Big Sister from our time in Chicago but she opposed me on my methods and discretion. I made a note on my calendar and continued my preparations for the date. We hadn't seen each other in over a year.

"I'm in love and feel great. I want the best for you, but I need to see you soon Louisa." Tess was a good friend and we would settle the date next week.

She was of course worried I might be gliding on my looks, not bringing Charles to be aware of my gender history. She was a bit correct but somehow I felt he knew, and wanted me just the same. I adjusted my pantyhose and settled my breasts into the bra. The thong furthered the restriction of my clitty. I was nearly as smooth as a genetic girl. Tess's call had reminded me of the number of lesbians that were attracted to me before I had breasts and my body was altered by the hormones.

I checked my pocketbook for the usual protection and make-up items, then applied a small amount of parfum. The slip and dress were adjusted as I reviewed my outfit at the door. Some wrist bangles and a ruby necklace were the final touches. I considered the possibility that Charles was going to detect a surprise and run. Looking back to the mirror I considered the possibly. No way!

"Madeline, I need to visit a friend in Manhattan. Can you get away later next week?" Tess was anxious about her friend. Louisa was a truly stunning beauty but she was still at risk. She wanted men to be attracted to her beauty and almost never explained that she was in transition.

"I can't stay away from Louisa. She could be hurt, but maybe not. Can you travel with me sweetie? I'd love her to meet you as well."

Dressed just so Louisa moved along the sidewalk. She was comfortable with herself, sharing a flirty moment with a gray haired gentleman as she stepped along on Sixty-fifth Street. The bar that Charles selected was a mere two blocks from her apartment. As she walked she considered the coincidence. Could he have found her on-line, her address? The thought vanished for she had arrived, pulling open the door and found him seated at the Bar. He stood as Louisa approached, his large hand extended, a soft smile greeting her. She was vulnerable and knew it. She quickly ran her eyes over Charles, missing his doing the same to her slim tall figure. He was a real hunk and his crotch seemed to portent a fun sexuality. Louisa resisted a too familiar hug and grasped his hand, while he helped her to a seat. Charles observed her choice of hose when her skirt rode up a bit. The toned material running deep passed the hem of her dress.

Their evening went very well; sharing an hour and a half, a delicious wine and they were both very happy to have met. Charles didn't want the date to end but he realized that Louisa might not feel the same. He smiled and saw when Louisa moved slightly her pert breasts encased by the simple bra.

"Can we get together again soon, maybe Wednesday after work?"

Louisa wanted to but remembered her rule. She was very excited being near this man. He was special and he wasn't making her feel anything other than beautiful.

"Can we talk after the weekend is settled? Charles, I don't want to rush anything. I do like you but I want to go slow ok?"

She paused and continued, "You're wonderful and this was a great evening and I'm excited for our next meeting."

He smiled and grasped her right hand softly "I agree this was nice and I understand Louisa."

He suggested that he might walk her to her corner. Along the way he paused under a street lamp to look at Louisa.

"I enjoyed this small date Louisa, but I'd love to take you to dinner sometime soon?"

"I had a lovely evening Charles. Thank you."

Louisa smiled and took his hand and kissed his cheek, "Actually, I'd love that Charles. Here's my cell number." She turned and walked a few steps. "Please call me soon." She walked north a few blocks and turned west.

Walking away from her new friend she reviewed the subtle signs of his awareness. She was all but certain that he knew she was a 'new' girl. She paused to consider why she'd not just come out and said so. It worried her that her confidence was a bit shaky. But she had an agenda; her mind was filled with his scent, his body and she had to dream about these details, had to plunge her pussy as soon as possible.

Tess called Louisa mid afternoon Sunday. "Can we stay with you or should I book a room?"

Louisa was excited to see her, meet this new special lady and spent some time together.

"I haven't an extra room dear, this is Manhattan Tess."

"Ok we'll stay at the Four Seasons. Can you meet us there two weeks from Friday, late afternoon?"

"I generally have an meeting Friday until almost 6pm, so maybe dinner at the Hotel?"

"Sure, that can work. So tell me about him. Have you revealed any special news?"

Louisa instead distracted her with news of her job, her new breasts and anything other than responding to her question. Tess could see this trip was important. She needed to help Louisa and would be happy to help soften the news to this new man. But she considered the situation; three beauties in tow, and he's told two are tranfemmes? It would be too much for any man. She needed a plan to advance Louisa's relationship, young as it may be.

"Can we meet Charles, maybe that Saturday for lunch?"

Louisa considered the question. "We've only just started to date Tess. Let's see how things proceed during the coming weeks ok?"

"Oh, sure, I guess I misunderstood. I thought you'd been seeing him for more than a month."

Louisa gave Tess the particulars of the on-line relationship and the last date. "I'll see him on Wednesday." She'd decided to pursue the date for lunch. She was beside herself with lust for Charles, though they'd only barely kissed. Tess talked a bit of her new girlfriend but was reserved pending the trip.

"So we'll see you in a few weeks, be as good as reasonable Lulu."

The rest of Sunday was quiet and she decided to retire with her toys. Sometimes Louisa would just make love simply and quickly but she had all day. She drew a bathe with oils and while it filled she selected some lingerie and accessories. The dark waist clincher without garters wasn't a necessity but it slimmed her profile. The suspender was a beautiful dark grey with a wisp of lace and six clasps. The thong was nearly a string but she didn't need to hold a big clitty. She recalled a mid length chemise that would go nicely with the set, but no bra this afternoon. The hose were seamed; getting them straight would take a few moments, but the welt was divine lace almost 4" along the top of the sheerest black silk.

Her toys were stored in a Kitchen drawer of all places. The longest was over a foot but slim. The shiny pink double-ended dildo was selected and set on the bedside table. Now to the bathe, oh, she wanted some soft background sound. She decided to run a DVD movie of a group of wild women doing sexy play, but which one? She selected a title "Mary's First Anal" and opened the machine.

Slipping into the water with her long hair up she relaxed and considered the decisions and possible outcomes. The soothing water caused her mind to pause and just enjoy. The small clitty was now tiny and she arose to her knees and cleansed her bottom. Stepping out to the mat and drying she saw the movie's character inserting a long dildo into her bum. She noted her heart rate and moved nearer to the screen as she began to dress. The girl in the movie slowly continued to slide the toy in, a bit deeper, then nearly remove it, only to re-insert it even deeper. Lulu wasn't certain of the girl's toys length but it nearly disappeared into her bum.

Padding her skin dry she turned to put the clincher on her torso. The last time she'd checked her waist was at 27". Lulu walked to collect her fabric tape. Before placing the tight garment about her waist was now at 26". Not too proud, she smiled and looked at herself in the mirror. The clincher now settled on her hips she gathered the drawstrings bring her waist to almost 24". Gathering the suspender belt about her narrowed waist she settled the garment and reached for the first piece of silk. Once the right three hooks were attached to the long hose she slipped into the 5" black stiletto. With the left hose and heel on she returned to the DVD and watched the long thin object disappeared into the girl's back passage.

"Oh my God, she's taken that whole toy inside herself!"

She considered her toy and returned to do her face and brush out her hair. Stopping to notice the finish on her toes needed attention. She grabbed the soft pink colored bottle and completed the digits. Reviewing her hands she decided they were acceptable. Out of the corner of her eye she noted that the girl had removed the phallus and was sucking on it greedily with a second beauty on the bed with her. Lulu smiled realizing she was going to attempt this wick act, burying her dildo within her ass.

Louisa was a bit excited but she moved about the apartment enjoying the luxurious lack of purpose. The whole of her person needed to be fucked, and she would play for whatever time. Just taking her time. She went to the window and opened the shades, though she wasn't fully dressed. The light cast across her upper thighs and the sun caused glare to her eyes. For several minutes she simply stood watching her neighbor windows, unconcerned about who may be observing her poise and dress.

Charles wasn't paying attention to the game; the Colts were controlling the Giants. His attention was on a note he was composing, to his new friend Louisa. A beautiful girl, in his thoughts the most beautiful he'd ever met. His terraced glass wall faced north and therefore was always in shadow. Hence he tended to look about at the activities across the inner block. He wasn't curious enough to have a pair of spyglasses but he did find the world on the northern block interesting. Some of the neighbors didn't close their blinds even while naked. Others were like clockwork, open during the evening but shut for bedtime. He hadn't been able to deduce any special individuals until now. Just beyond the edge of the flatcreen there was a beauty clad only in lingerie standing in front of the partially open drapery. She was beautiful but too faraway to clearly see.

Just as he stood to get a closer look the woman turned and move off, then the drapery closed. He noted her blonde hair was atop her head and saw she had a long neck and lovely sexy legs. Returning to the sofa he considered his new friend and hoped she had assets as nice.

Louisa moved to her bedroom and caught sight of the two girls using a very long black fake cock in their asses. She settled atop the bed and considered how best to use her toy. Reaching for it she smiled and considered the realistic head. Slipping it into her mouth she licked about the long shaft. The length was possibly 14" or four of her hands. Slipping her thong panel aside she moistened her rosebud. Though she had already lubed, her saliva was nearly perfect and she tasted her moisture from the bum scent on her fingers. Maybe try this on her side? She rolled to her left hip and using her right hand rested the phallus at her opening. A small gasp still escaped her throat as the head moved passed her first muscle. Pausing she checked to the video. The one girl was stuffing the other girl's bum with the black toy. She followed suit and the dildo entered into her valley to about 4", she rolled to her tummy enjoying the fullness. She contemplated the toy and her cavity. How did that long cock get so deep within the girl?