Let me set the stage! I am a former offensive lineman, quite a jock, strong, bulky and blockheaded. To look at me you would think I was all man, the epitome of a macho man. I also always thought of myself that way. I could rip the head off any one my size. I dated cheerleaders, the girl next door who was enamored with my football prowess and the groupies. I had it made for the most part, the kind of life most men would kill for.
I was in downtown Miami one night while I was attending UM on a full boat scholarship. I was drinking and bar hopping and very high. I came stumbling out onto the street and nearly knocked over a woman as I tumbled out of the bar. It wasn't until later the incident changed my life. I was very embarrassed, for being so drunk and clumsy and I helped her up, all apologies. She said in a husky voice, "You're a macho asshole!" I gave her the once over and realized she was a man dressed as a woman. I was appalled but at the same time deep inside I was turned on. I found her/him very attractive.
Not five weeks later I was hit by a high low in a game against Alabama and my knee crumbled like a twig. MY scholarship was over and I was a partial invalid with no hope of playing Pro ball which was my plan all along. I went into rehab, doing all I could to resume a normal life but the drugs and depression got to me. I was spiraling in, giving up on myself. I was so depressed because my life plan was over.
I would buy a six pack and a bottle of Canadian Whisky and hole up in my room after therapy. I would shoot the pain pills with a boilermaker and drift off into a surreal world with no pain and lots of wild dreams. I passed a lot of my lucid time surfing the web. At first looking for porn and beating off then passing out from the pain pills.
In my dreams I found myself conjuring up the man in the women's clothing. She seemed to re occur and reoccur. When I was lucid I started looking for web sites about men dressing as women. I found out they were called cross dressers or transsexuals. I then looked up some x rated sites and found myself very turned on. I whacked off many times to the she he's there and then passed out afterwards, knocked out by the booze and drugs.
I found myself when drunk imagining my self dressed as a woman, smelling like a woman, wearing sexy cloths and having men fawn over me. I tried to drink it away but the dreams and fantasies persisted. I went into Walgreens one day and bought some muscle cream and found myself buying some plum nail polish on the way out. I blushed at the checkout counter but the clerk just rang it up and made my change.
I had a full raging hard on as I applied the nail polish to my toes that night. I had never felt so sexy or so shameful. It wasn't until the next day when I had therapy scheduled that I realized I need to get this off. I panicked for awhile until I realized I could wear socks and shoes and no one would be the wiser. The whole thought of that made me a little ramie.
At therapy, I worked hard and my knee killed me, I still tried to push through it. Brigitte my PT kept pushing me, so I kept trying. When we finished she complimented me on my hard work and said we need to strip you down and soak the knee or else it will swell. I was mortified. I tried to cogole her into letting me take a hot tub at home but she would have no part of it. Strip down young man and get in the tub" That was her last commandment as she turned her attention to another patient.
I went into the locker room, a place I was normally at ease with and debated what to do. I put on my street cloths and high tailed it. I went straight back to Walgreens and bough nail polish remover and some cotton balls. I also bought another two colors of polish, since I was there and had the remover anyway! I picked up some snacks and razor blades and male deodorant and stuff to make it look like I was buying stuff for the whole family.
I got home and removed the plum nail polish. I was very relieved, but twenty minutes later I was applying silver nail polish to the same nails, and when I finished, I applied it to my fingernails. The whole time I was drinking and of course taking my prescribed meds.
I had a day off the following day and woke up with a killer hangover and was shocked to see my nails. I was sick to my stomach but so turned on I had to jerk off. I opened the fridge and popped a beer had a few sips and filled it back up with whisky. I spilled out some pain pills and muscle relaxers onto the counter and took a couple of each.
At the computer, I got on line and started to punch up a T.G. web site when I wondered if I could find women's clothing in my size. So I punched in xxxl women's clothing. I looked at the results and it asked if I meant plus sized clothing? I checked the box and found whole 70 pages of sites that sold large women's cloths. I opened a couple then found one that offered measurements and found out I would be a 3x or a 32. I began searching for cloths in my size.
The options were on the left and I of course went to lingerie first. I looked at teddies, slips, night gowns and bras and panties. I was blushing just looking, and yet at the same time so turned on I couldn't stand it. I got up and made another r boilermaker, when I returned, I got serious, and I compared sites and prices and quality. I found a site that specialized in gowns, sexy dresses in huge sizes. I finally decided a black dress with a medium length skirt and pleats would look good on a big man like me. I double checked the size and went ahead and put it in my shopping cart. I felt so powerful when I made the decision. Then I went back and found a site that offered undergarments, I bought seven pairs of assorted panties in my size, a dozen bras, hoping thy would fit. And last but not least a few slips, half slips, and full slips in several colors.
I was so hoping all the cloths would fit, and I was so turned on to know all my feminine cloths were on the way. I had another boilermaker and did something stupid. I took a couple pills and got into the car and drove to the mall.
Before I left, I had the wits to remove my fingernail polish. I went straight to the department store that offered makeup and perfume. I was needless to say, three sheets to the wind, but that worked in my favor. I was UN flappable. I went to the makeup counter and said, my daughter is turning 16, she has the same skin tone as me and I want to surprise her with a whole makeup kit. I want the best quality I can get. I now had her full attention. She sampled many items on my hand and I was an easy sell. I walked away with over $300.oo of makeup. I then went to the perfume counter and gave her a similar rap. She demoed a few perfumes before I found one that gave me an erection. I took a box with perfume, cologne and body wash.
I was pulling out of the parking lot and smiling when I suddenly thought about body hair. I crossed the street to target and went into the women's section. I bought fancy shampoos, women's deodorant, and I looked at razor blades and while I was deciding I saw depilatory. I read the box and bought several boxes.
When I got home I was dying to dress up and clean the hair from my body, but suddenly remembered my therapy sessions.
I had to wait, damn I was frustrated. I did my meds followed by a boilermaker. I was too turned on to crash so I tried TV. After a few moments I realized I would not be able to wait. I went in the shower and spread the depilatory all over my body. I go the shampoo out and the other girly stuff and set it up for after shower. After the time expired on my depilatory, I got in the shower. As I washed, my hair fell off as if I had cancer. I was not so impressed until I took the towel off the shelf and felt how sexy it felt against my bare skin. I applied the skin lotion all over and put on some body lotion and perfume.
As I exited the bathroom I was boasting a full hard on. I went straight to bed and jacked off a full load...
In the morning I had therapy, I was mortified by what I had done to myself the night before. I took a shower erasing the feminine smell and took off my nail polish on my toes but I knew I would soon be exposed at the therapist.
Brigitte greeted me and we got right into our session. She came back after a few moments check on me and said" You seem different, more relaxed!"
I just smiled a lopsided smile
My knee hurt like a bugger but I was getting away with my new lifestyle.
Brigitte came back and made me work harder and then leaned in close and said. "You are very sexy, what is different about you?"
I smiled lopsidedly and told her I am discovering myself.
She gave me a wide smile and said "we need to have lunch after the session. Would that be ok?"
I just tried to smile and went on with my session.
We met later for lunch and Brigitte acted a little antimated. She ordered quickly and ordered for me as well, you need more vegetables she said.
We settled in and after an uncomfortable silence she said," I hope I am not out of line But I noticed traces of silver nail polish on your fingers today. Please don't be embarrassed."
I blushed none the less and scoped out y nails.
She took charge and said," I think it is great that a perceived macho man can explore his feminine side." I think men can be as feminine as women. I just want you to know I will never tell on you and I actually admire a man your size exploring his sexuality.
With a full flush on my face I relied, "Thanks"
The thought of all the sexy cloths coming in the mail, just popped into my head and I blushed even more.
Brigitte said, "I have a brother whom is a transsexual and I have a lot of sympathy for him. Being a cross dresser or a transsexual is very tough and I want you to know that it does not bother me or freak me out, I will be as supportive as I can, so please relax around me and be yourself."
I was stunned, I couldn't believe my ears. I just smiled and nodded. She dropped the subject all together and we ate and paid our bill with out any further mention of the new me.
Saturday my first package arrived. A plain brown package with a simple black pleated dress. I opened it and smelled the fabric. I held it up and then got up the nerve to try it on. I was happy with the fit, because I was so big, the high waistline fell above my ample waist or hips and I was surprised how nice it fit. The size chart was right.
I at once got on the internet and searched wigs. I knew a short style would suit my big body best, so I found a cute blonde wig that cut right under my ears and had a lot of sass.
I ordered that one and three more just in case. I had to go into the bedroom and jack off again.
Monday the other packages arrived. I had been up for two rounds of drinks and meds. I immediately opened the boxes and with a massive hard on, tried on all the clothes I had ordered. The panties and bras were an exception turn on. I realized I needed breast forms to fill out the bras, so I goggled them and placed an order. That night I dressed as a woman for the first time, I shaved my body and perfumed myself and started from panties and bra up. I put on a ¾ length slip and slipped my black dress over. I had such a hard on you couldn't believe!
I looked in the mirror and was shocked how good I looked. I was a plus size woman alright but if I had nice hair I would pass for a sexy big woman. This was unbelievable; I had to take advantage of myself.
On Tuesday the wigs arrived and I dressed again. Again I was so turned on and made love to the new me. Wednesday I had a physical appointment and Brigitte, out of character kissed me on the cheek as I came in and gave me my work out. She paid special attention to me all morning and when I went to leave she asked if I would like to go out on the town tonight?
I assumed she was hot for me until she said, "come over and I'll do your makeup if you like.
MY hard on nearly answered. I stood with my mouth open for a few seconds and realized what a gift this was. "Please I managed.
Brigitte had me confused; I never expected to have such an ally especially in the female camp. I had assumed that men, gay men at least would be supportive. I was fascinated by the idea but still very uncomfortable. I did a round of pills and opened a bottle of red wine and had about half as I gathered my stuff and packed a bag. I finally decided that if she was game, I could use all the help I could get. I showed up at her apartment and she kissed my check and let me in.
"Did you bring your make up and cloths? I blushed and nodded yes.
She grabbed my hand and took me straight to the bedroom where she had a bright makeup light and dressing table. I opened the top of the bag and handed her a bottle of wine and she said, get comfortable hon. I will open this and be right back."
I felt awkward but very excited and decided I was in a dream so why not roll with it. I opened my bag and took out the makeup box and went to the bathroom to shave closely my face. I came back and Brigitte was back with the wine and we sat down and clinked glasses. She felt my face and smiled approvingly.
Like we had been brother and sister or sister and sister her whole life she inspected what I had brought and went to work. She applied foundation, and then made up my face. When she was finished, she asked to see my wig. I took out all three and she had me try them all on. I suddenly realized what she had said at work and I panicked. "You're not expecting me to go out in public dressed are you?
She just smiled. Let me see your cloths. I opened the bag and laid all I had on the bed. She frowned and perused what was there and then handed me some black panties and a bra. Put these on, she held up the dress and smiled, "Nice choice, every girl need a basic black dress." I blushed.
When I returned from the bath room in panties and bra, she took a sip of wine, stood up and looked me over with a critical eye. I have a couple breast forms; we need to fill you out a little. She fitted them in my bra and then said go ahead and put on the slip. I slipped it over my head and the satin feel made me aroused as it came down around my bare skin and hairless body.
Brigitte looked me over again and asked about shoes. I told her I had yet to receive the oversized shoes from the catalog company. "Mmmn she moaned, and then she said you can wear panty hose and everyone will focus on your body anyway, and will think you kicked your shoes off to dance.
Now I really panicked, she was planning on dancing, that was too much. I was about to object until she said "Go ahead and put your dress on.
With a critical eye she looked me over and said turn, more to the right, there, mmmn yes very nice. Do you have a scent? I gave her a blank look. "Perfume?" I relaxed and smiled, oh yeah, here. She checked out the label and said wow this should do, very pricy. I guess nothing is too good for a real girl.
She showed me how to put on perfume and we drank another glass of wine and discussed her brother some. I took another pill out of my pants pocket on the bed and slipped into my mouth when she wasn't looking. I chased it with wine. We moved to the kitchen and she looked me over. "Oh my God you don't have a purse, you have to have a purse, and she hustled off to find one for me. When she returned, she had filled it with lipstick, powder and perfume. A couple Kleenex and a cotton ball or two filled out the little that was in there. You need to take your wallet too, they might card you.
I was feeling the last pill and decided to roll with the punches. I shoved my wallet into the purse. Brigitte laughed and grabbed it from me. She removed the wallet and took out my id and some cash and placed those in the purse. Most the drinks will be bought for you, but a girl should have cab money."
We walked out hand in hand and she took her car. We went to Miami Beach and as we crossed the causeway I began to get paranoid again. "Brigitte? Do you think I will really pass? She reached over and squeezed my knee and smiled.
We arrived at a club called The Leo, with a neon sign that boasted a lion in orange colors. The car hop helped her out and a man opened my door and gave me his hand to help me out as well.
She shot me a smile and tipped the guy and gave him the keys.
We waltzed right past the doorman and were inside before I could even scope the place out. I have to admit I was in a hurry to get off the street in case someone recognized me.
Inside it turned out to be a gay bar, maybe a drag bar, I don't know but there were many kindred spirits here as well as a lot of limp wristed men. I suddenly realized I was in my element and relaxed slightly. Brigitte smiled and made sure we got a table. I was still pretty stiff but I have to say the crowd had me very titillated.
Brigitte took charge and ordered us umbrella drinks and grabbed my arm and asked me how I liked her club. I smiled and said well I am not petrified, I thought we were going out to a regular club or restaurant and I was terrified.
She smiled and brushed d my cheek with a kiss and our tall drinks arrived.
We toasted over the noise by holding the glasses in the air and smiling.
We looked around and took in the ambience. The place was hoping, Men were kissing, transvestites were kissing men, each other and women were kissing each other as well. I had never dreamed there was a world like this. Between the drinks and the pills and the new me, I was so relaxed and horny. I for the first time in my life felt like I was as close to heaven as it gets on earth. Brigitte must have sensed it and tipped her glass toward me again and we drank again.
Just then I set down my glass and a nice looking well groomed man with a mustache leaned down and asked me in my ear if I wanted to dance. Brigitte sent me a smile and a look of encouragement.
I felt trapped between panic and ecstasy, I took his hand and stood, I towered over him and he smiled at me, taking my hand and leading me toward the dance floor. The current salsa hit was blaring and he placed his arm around my waist and led us through some very graceful Latin steps. Just as I was getting used to following him, the song ended and a ballad came on. His eyes besieged me to stay and slow dance with him I Had no choice; I was too embarrassed to head back to the table.
He pulled me to him and our bodies met as the beat ticked on. His hips moved in Latin style, his body rubbing on mine. He looked me in the eyes as if to say "are you enjoying our dance?"
Right then as I smiled back, I felt his hard on. He was definitely holding it to me. I looked and he smiled and pulled me tighter. I didn't know if I was excited or appalled. I was too embarrassed to leave, so I decided to go with it, I found myself a little hard as well. His errection got firmer and he kept me tight to his body. I felt very good, so I leaned my head down and laid it on his shoulder.
We swayed for a few more seconds and I felt his lips kiss my neck, his hand lower on my back, almost on my butt. Surprising myself, I found I was very erect, afraid he might feel it and go further. He just smiled and kept me against him. When the song ended I gave him that's enough dancing look and he walked me back to the table, holding my hand the whole way. I
"I am Jorge he whispered, I would like to have another dance when you like. I smiled, and glanced at Brigitte. She gave him a smile and dismissed him with her eyes.
Our bar boy showed up with two fresh drinks and whispered into Brigitte's ear. She smiled and leaned in to tell me the drinks were from a table of handsome men three or four tables toward the stage. I followed suit as she raised her glass in a chin chin to them. They all tipped their glasses and smiled.
After the next sip of my drink I felt the room spin, the booze and pills were taking an effect on me. Brigitte noticed and asked if I needed to go home. I thought for a second and said yes. We cashed out and she walked me by the arm to the door.
I was heartbroken, I wanted to stay but I was way too loaded to stay.