tagTransgender & CrossdressersDressed So Ch. 05: Tess' Friend

Dressed So Ch. 05: Tess' Friend


The following is the Fifth chapter. This is the continuing story about Tess and her friends. Please consider reading the earlier submissions to understand the development of these special Ladies.


What was I doing! I had selected the file including my image and pressed send. I hadn't considered the possibility that Charles would react negatively to my looks. Well, maybe I was a bit anxious. I had been living as a woman for nearly seven months when I ventured out as Louisa. I had made the images almost a week ago, after having spent two and a half hours preparing myself; I wanted just the right outfit, my long blonde hair styled and my face on. I liked to wear my hair up during the Spring. The affect showed my long neck with a simple pearl pendant.

Nothing of consequence developed from my sending the image file. Charles and I had been connected on a dating and chat service. After both having completed the usual profile the service's computer had matched us. Actually it had produced over 80 matches for me and I'd selected Charles as the best after studying the numerous candidates. I hadn't misled anyone but in the profile the question and boxes for gender offered a chance to be less specific and I checked "not saying". Together with my image I felt it was clear I was a transwoman. My other attempt at the on-line matching, before I'd completed my transition, had produce a lot of attention but from clearly a group of men interested in a one night sexual relationship with a tranny.

I had decided that I would only continue using a dating service if I could attract normal guys, and I wouldn't conceal my personal situation. The profile questions didn't require a declaration of my sexual history hence I didn't volunteer I was born a good-looking boy of 69" height and near a 160 pounds. The "not saying" selection in a profile was just for someone like me. A guy interested in gender girls wouldn't cruise the "not saying" selections, or might he?

After a strict exercise and diet regiment over nine months I now fit a size six, though my hips were naturally wide at just less than 38 inches. Having lost those 28 pounds had been a lot easier than I'd thought possible when I'd started. My body had acclimated to the workout and eating healthy foods and salads turned out to be delightful. I just wish my hormones hadn't produced my bosom. I was now a pert and full 35 C cup; I wanted more of an athletic chest, say a B instead of the attention grabbing points I developed. I was getting too much attention around town, even waiting at Starbucks, mostly from married caffeine addicted businessmen.

At the start the job search had proven to be a challenge as well. I was trained as a Graphic Illustrator having completed my Masters at Pratt ten months ago. After many employment rejections I simply found a physician in a small eastern state with a less aggressive policy towards gender changes. The doctor had to certify my new sex and my attorney prepared the documents. I easily changed my license and it was a lot easier to describe myself as female rather than explain away my genitals during an interview. But to protect myself from discovery I decided not to entertain the numerous dating requests from colleagues. After three months of working in the Ad Design office I spoke with the Managing Partner about the behavior I described as 'near harassment' I was encountering. I'd taken to wearing a ring on my left hand but the comments regarding my 'coldness' and social exclusion were troublesome. Fortunately my skill level had developed quickly and it allowed the firm to grant my request to work from my home office two or three days a week.

But back to Charles's respond; he was so taken with my standing shot! I had worn a knee length dress of a simple design and a tall pair of heels, but the dress hugged my slim frame and wide hips and he wants to meet this coming Saturday. My cautious approach made me set the date for 4:30pm at a nearby wine bar. We'd try a short date with the agreement to not lead into dinner. I thought that provided a sufficient amount of time to discover something about each other. A second date might be arranged but I didn't have to promise. I was in charge of the conditions. At least that's what I thought when we spoken by phone Monday evening.

I must share that I found getting ready for this new experience to be exciting. I'd met up with other men (and several women and 'girls') prior to my transition but each of these dates had taught me that I would never be treated as I wished. Though very passable I knew I felt I wasn't truly ready and therefore it affected my behavior and my date's attitude. The men sometimes noted something that brought a question. Never an outright question such as 'are you a guy', because I easily passed as a twenty-something girl. With each it was something different. Several were aware I might be concealing a past and found an excuse to leave quietly. Two were a bit too turned on and made salacious requests that I won't dignify be reviewing.

I did date more than one man, several in fact, who clearly enjoyed my sexuality. Michael was one who was special and caring. We spent several nights together at a Hotel, he was a great lover and we enjoyed ourselves. He was beautiful and caring but was a bit too gay for my life. We're still friends and I can count on him in a pinch, in fact we hooked up again right after I went fulltime.

One of the women I met was just terrific. She enjoyed helping me dress so our dates started at her apartment. I had only been crossdressing when we met a little more than two years ago. I was even then very passable but my behavior and manner of moving was a dead tell. Donna enjoyed helping me but she offered instructions only by full immersion.

"I'd love to teaching you Lulu, but I'll do so only when you're fully dressed. You look like a woman dear, but you do not act like one of us. The walking, sitting, the manner of your speech and subtle movements are an important part of being a woman. Your body and face are going to shake up any boy or girl that meets you. But you need to adjust so many small actions. Now let's get you dressed and do your face. Your rats nest needs some serious care as well."

Donna loved to play with me in bed after these lessons and I loved to explore her body too. During the next few months she taught me how to buy clothes that fit properly, shoes that weren't too slutty, and how to treat my skin and cuticles properly. My near the shoulder hair was always an issue and therefore when I'd let it grow out she took me to a hair salon for an appropriate longer style. We had spent nearly three months hanging out when I asked her to fuck me. All of our previous sex hadn't included penetration. She was in charge in bed and she agreed on this occasion to insert a special toy and do me right.

"Lulu I want you on the bed, atop the pink wedge. Yes, young Lady, lie across it, bum up please dear. Lulu I can't see your tight little hole."

Donna was dressed in heels and a chemise but without a thong, "Come on, spread you legs a bit. That's better, and so cute."

She move to the edge of the bed and her fingers were playing at my rim and her tongue licking lightly, "Make it wink at me Lu."

I listened and complied, she liked my willingness to submit, and I wanted to have her thick play cock sliding deep inside me. "ohh that's delightful Donna." She teased my bum for quite a long while.

"Women love to have our bums licked though most of us don't like anal. Humm, I enjoy seeing the garters framing your bum. I hope you're wet dear, this is the big one" she approached the bed and probed my tight opening with first her long finger and then slipped her middle digit inside me.

"Remember that you wanted it this way Louisa."

She came behind me and slowly slipped the head into my bottom. Donna paused for some moments before she started to press her fake cock into me. "Does this feel good sweetie?"

"Oh yes Donna, but slow, that's better. Maybe angle downward a bit; yes, yes, Donna" I said looking over my shoulder. A moment later she was completely buried inside me. She seemed really focused and I considered whether she was enjoying the scene.

"Do you like fucking me, filling my bum mistress?" and then I saw her smile.

"Yeah Baby Lu, I do like this, and the toy is getting me off as well."

Her orgasm arrived a bit before mine, but her cock didn't stop and I exploded into my tight thong. She moved beside me on the bed and we made out until she was ready for another try.

"I'm happy you're enjoying this type of play Donna." She reached into my panty and lubed the cock with my wet seed. And than she rolled me and mounted me again, though this time I could see her smile and eyes.

"Well, I just didn't see how I might enjoy stuffing a cock into an ass. But yours is quite an ass Louisa."

The lessons continued for many months while I completed my studies. After we'd been dating for nine months she told me she wanted me to prepare for SRS. She had come to regard me as a lesbian like herself and she wanted a partner. She wanted to share everything, and I was surprised and couldn't dream of letting her know it wasn't in my plans. She was 32 and wanted a baby, ours, not an adopted child. The idea of me making this commitment, just after having completed my degree, than to move into her home and get a legal marriage?

"I love your little cock Louisa but I want you to have a true pussy. Fucking your ass is just not the same dear girl. We'll save some of your essences for the right moment ok?"

I had moved toward being a bit submissive but I knew than I needed to end our relationship. Her doctor had helped me arrange a better, focused, hormone treatment and my breasts were so perfect. Being with Donna had allowed me to evolve and my personality and manner had developed fully; I was feminine. My closets were full of everything except long gowns. We'd shopped together when we found an opportunity and her advice helped me develop a complete wardrobe. She had made me a more aware and dainty girl, and my tight bum could accept all of her various toys, but I wanted something she didn't have. I wonder about moving out and away but I knew what I had to do. I wanted a man and his warm phallus. We parted badly, and she cried so much. Eventually Donna adjusted and after a few months we are now friends, but we no longer sleep together. In fact she's found a new girlfriend whom I really like.

Donna's new lover is Sarah and she has been advising me since she and I met about a month ago. She told Donna when we met that I could become a very special transfemme if properly nurtured. Sarah had worked as a catalog model and knew several transgender people in the City. She introduced me to a dear older transfemme who offered guidance on the legal and emotion issues I was addressing. There were of course obstacles, my genital package should be addressed. Her friend recommended I have my testes removed as soon as possible. I struggled with the suggested but had the procedure done later that week at a clinic specializing in gender cases.

I was ready to be treated as a woman, albeit without a vagina, and now I hoped this possible new friend Charles would do so. He seemed to be interested in me as such. I'm unconvinced he knew then how my world had been changed. We met in a chatroom for singles, without any pretensions. He was a handsome guy and I was, a girl, just looking for someone to care for and be cared for, maybe to be loved? He didn't act like the others, and I think I was somehow different as well. I didn't go on line unless I was completely prepared; I didn't chat in a robe and slippers. Maybe because I was dressed, my hair and face done it affected my demeanor, and my personality. I guess its because now looking back, I was a woman. I was no longer a boy who wore a dress.

That night we started our chat I wasn't dressed to go to a club, sexy hose and sky-high heels, a short skirt, but in a simple yet beautiful print dress and pantyhose, and black heels about 3" in height, with a shell necklace and earrings. I'd touched up my makeup for the evening, having shower when I returned from the office. My dinner was a small salad and fruit, to help keep my skin clear, and my waist slim. I was surprise when he came on line, a bit forward yet his icon included a small image of him smiling. He made an introduction, I guessed by our very near addresses; we were in the same city. He seemed to treat me with respect and I wonder whether we'd met. On further thought I realized that wasn't possible. After we'd stopped chatting I still wondered about his kindness and almost an awareness of my recent past. He was sensitive without prying.

Three months earlier I used another dating service based from Philly hoping to have some anonymity. I'd met someone, a tall blonde haired man about 31 years old from that City, and we were clearly attracted to each other. After two weeks of chatting we arranged to meet in Princeton. I'd gotten a room at an in town Hotel to prevent a difficult Saturday night drive back to New York. The drinks at 6pm lead to dinner, and then a long walk in the moonlight on the old Campus. He seemed to understand my sexuality, though I'd been a bit bonny, enjoying his nearness. We paused and he hugged me close and his hand moved to my near flat mound, as if assuring his decision to bed a transfemme. He kissed me,

"Don't run away Louisa, I want you just as you are."

I returned his kiss, deeply frenching his tongue, "You don't have to ask twice." I said.

We walked back to his large suite overlooking the Square. I wasn't drunk nor was I looking for a longtime lover. I just wanted to suck his cock and have it deep inside me. I slipped my black A-line off of my shoulders and approached him in my chemise still wearing my heels. I pulled away his trousers and pants to find a thick and semi-hard cock. My tongue ran down his length before I settled my mouth on his helmet. This man was getting hard while I was getting excited.

"I love your cock, especially because I'm making you hard with my mouth."

He smiled at my comment "Suck me Louisa, I'll get bigger still dear girl. Ahh, watch the teeth honey, ohh, wow, you've got me deep baby, into your throat?"

I couldn't though I tried; he was huge now. I stopped for a moment, stood and pulled him holding his cock toward the bed. "I'll get a bit more comfortable" as I removed the chemise and my bra.

"That looks so sexy Louisa, I like the thong too, and wow to your stockings."

I had prepared to attract him and it was having an affect. I bent to release the clasp at the left hose. "Please leave them on honey."

"I'll bet you want to fuck me with my heels on too big boy?" I said smiling lewdly, and rolling my hip.

"Come and sit on my nice cock dear girl. I want to fuck you." I moved slowly toward him, dancing while I watched his dick quiver. I felt so beautiful, but my small clitty was concealed and hidden with the thong panel. I didn't intend to remove it; I liked keeping my clitty out of sight, therefore out of mind. I was a sexy woman and he wanted some pussy.

I slid across the bed to his member and went down on his cock again, well some of it was in my mouth. Pausing and adjusting my position I continued and his cock slipped deeper, deeper into my throat and I allowed it to rest there while I adjusted to the girth. Slowly I moved a bit, than slowly removed most of it from my mouth, but I wanted it deep inside my throat again. This continued and he seemed to understand that I was worshiping his phallus. My mouth was atop, than my tongue along this length, my left hand holding his balls, my tongue licking around and than sucking it into my mouth again. Thom tasted so good. I continued to suckle him, in and out of my mouth, the motion stimulating my body, in than I'd slip it out, back into my throat. I felt his hand move to the base of his cock, to get my attention.

"I need your tight butt atop my cock now girl. Come here." He moved to sit at the corner of the bed. I dropped to my knees and returned my focus to his cock and licked the helmet slowly and looked into his eyes, and than I moved up toward him, straddling his thighs and we kissed as I felt him center the helmet at my opening. He was so gentle as he slowly entered me. I could have been in heaven as each inch slipped deeper into my bum. For several minutes he continued his penetration, then he paused and we kissed, our tongues racing about each other.

"Louisa I'm about to fuck your tight pussy now, are you ready?"

I decided to take control and moved my hips off his truck and his cock slipped out as I reached the top of his helmet again. "Oh no you don't" I cooed, "get back in my pussy" as I positioned him and moved downward. I fucked him like this for some moments, than he flipped to a reverse position, his cock now sliding deep into me. Thom had his hands on my small tits, yet I was into this, his mauling my breasts. After I adjusted his pace he came quickly, filling my bum with seed.

"Don't go anywhere my tight little girl, I'll rise again in twenty minutes."

I oozed a little as I laid across the bed and casually played with his soften shaft, and sure enough he was mine again. I enjoyed sucking his cock for awhile, as he seemed to be napping.

His cock was solid though and I wanted it, "Hey big boy I'm going to fuck you." This time I was atop and controlled the session. I liked this position and he awoke, as I bounced on his thighs. He slipped from my opening shooting my ass and hose with his release.

We fucked again sometime late in the darkness of night, and I was oozing his juice as I fell asleep.

In the morning I was sore. I awoke before him and was still marveling at his size, but three intercourse sessions were all my tight rose could handle. He awoke and showered while I began to re-dress in my outfit from last evening. He opened the bath door sporting a huge erection.

"I'm too sore to take that monster again."

"Ohh no you're not sweetie. You're going to get fucked again," he said as he walked quickly to me, grabbing my arm.

"No please, but I'll give you a blowjob ok?"

With that I went down on my knees, in just my bra, my soiled stockings and thong. He was so large, and he seemed bigger than the evening before, but I managed to wet his length and was enjoying his cock, again, when he lifted me up, swung me around and licked my hole.

"I told you were mine to fuck again" and he set me down on my tummy at the edge of the bed and forced that sword into my boi pussy. It wasn't loving or gentle. He was hurting me as I tried to stop his thrusts. He held my shoulders tight to the bed, my head nearly covered by a pillow. With his left hand he pulled my one arm back around to restrain me. He fucked me so hard I started to cry, unable to stop him.

"I love your fagity tight little cunny and you look so beautiful when you sucked me off. Now I'm going to fill you with my juice you little boy whore." He came into me and then pushed me to the carpet.

"Now get out of my room you disgusting Fairy." I was bleeding from his penetration, but somehow gathered my things and limped out.

That wasn't my first error in judgment, oh no, I'd really made a bad call the year before out on Fire Island. I met another transitioning friend and we were on the Ferry over to the Island enjoying a bottle of wine. Gloria hadn't been as fortunate as me. She could get close to a drag look but didn't pass. She was ok with that, she was so sure of her femininity that she just dealt with the abuse directed at her. But we're on the queer boat together and a beautiful Adonis approaches us.

Speaking to me with a pair of bright blue eyes this hunk clearly wanted me. "Can you and your 'friend' join me tonight at a party? They'll be many other 'girls' and boys, maybe some whom you'll know, and we've got a DJ, plenty of booze and even a barbecued pig going."

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