The Deal Ch. 01

I would like to say my first time was beautiful and special, but while it was many things, it certainly wasn't either of those. To understand, you'd have to know how it came about.

For years, I'd been a secret crossdresser. I shaved my body, including my arms, all the time and told people I "just don't have body hair." At home, I'd pose in front of the mirror in miniskirts and heels, along with bras and makeup, and I always kept my hair long so I could style it like a woman when I "played dress up."

It took a lot of work to make myself look like a woman, aside from my shaved legs, which were long and shapely and had I been born an actual woman, I was certain they would inspire lusty feelings in men. The thought was so pervasive that, although I kept my crossdressing a secret, I started wearing shorter and shorter shorts so I could show off my legs.

Nothing gave me a thrill like when I'd notice a man checking out my legs, or when a woman told me she wished she had legs like mine. I was twenty-four, generally shy and never assertive, and I'd never had sex with anyone. Women didn't seem attracted to me. They liked me, but generally wanted to "just be friends," and when it came to giving me advice they always came back to "you need to speak up and stand up for yourself more."

The way I was seemed to contradict the fact that I was being very daring by wearing short shorts in public with shaved, tanned legs that looked like I stole them from a woman, but it was my fear of being called out or mocked that provided the biggest thrill.

I didn't walk around all day in shorts, and I didn't wear them anywhere that I would see my co-workers or anyone who knew me. I'd go out to the supermarket or the gas station and then go home. The trips were short, but as my shorts got shorter, the trips out also got more daring.

I'd moved away from where I grew up to start fresh following a number of disappointments. Maybe if I was somewhere that people didn't know me, I'd be more inclined to stand up for myself and be assertive. What happened was that I started wearing short shorts all the time, since no one knew me, and instead of being more assertive and masculine, I was nervous and scared most of the time. It wasn't just when I wore my shorts and showed off my legs, but in everything I did, because even the people I thought of as my friends were gone and I had no one backing me up at all.

Six months after my move, I had no friends. People at work seemed to be in a clique and generally gave me the cold shoulder. I did electronic receiving in a warehouse, but I told people back home that I'd found a great job and had made a lot of new friends. When I could convince them I was successful and happy, it felt like a victory over the people who thought I was too weak to make it on my own.

I started seeing this same guy around the apartment complex more and more often. It was as if we ran into each other every time I went to the mailbox or out to my car. His name was Bob and he started by giving me a standard, friendly "hello" when walking by. Eventually that turned into one-liners like, "We have to stop meeting like this," and "Good to see you again!"

One day when I was getting my mail, Bob appeared and began talking about how he was working the sound board at some local concert. It was apparently a big deal, so I went on to nervously say "that's cool" and somehow we had a conversation about music and bands that led to him offering to bring me some CDs of this band's music and of other local bands I had no knowledge of.

He brought them up to my apartment the next day. I invited him in and we sat and listened to the music and talked. It was a regular conversation any two men might have, but then, out of the blue, Bob cleared his throat loudly.

"Keith, I have to say, you have some seriously sexy legs and I think I need to leave before something happens..."

Bob began apologizing, saying what he was feeling was inappropriate and rude. I was speechless after the compliment, the first serious compliment I'd ever gotten on my legs, and I panicked, not wanting Bob to walk out of my life. On the one hand, I was starved for a friend, and on the other I was feeling all tingly and happy that he thought my legs were sexy.

I'd never given any thought to a man getting turned on by my legs. What usually happened was that a guy would notice my legs, check them out, then be surprised when he saw I wasn't a girl. When that happened, I'd act completely casual, and as if I hadn't noticed him. Inside, however, I was nervous, scared, and excited.

When Bob left I couldn't stop thinking about how he felt like he'd do something regrettable. What did he mean, really? I put on a miniskirt and heels after he left, a pink shirt with my C-cup bra with the inserts I'd ordered, posed in front of the mirror and began masturbating.

"Look at how sexy I am, how sexy my legs are," I moaned. "Bob wants my legs. Bob thinks I have sexy legs..."

It was all I could think of, but after that I tried to avoid Bob, which wasn't easy because his apartment overlooked the parking lot. That was how he "accidently" ran into me all the time. He was trying to meet me. After a while, he seemed to take the hint, and we stopped running into each other.

My habit of wearing short shorts didn't change. I got too much of a thrill being an exhibitionist. Being shy and introverted, showing off in this way caused my heart to race, and after what Bob said, it also gave me a constant erection.

Probably the only good thing about having a penis that, when fully erect, would be a stretch to say it was four inches, and about as thin as my pinky, was that it wasn't hard to hide in tight shorts. This had become my substitute for sex. After what Bob said, and how he left, all I could think about were men getting boners checking out my legs. It was bizarre, perhaps, but when I got home after a trip out it would take three strokes of my little dick to achieve a very satisfying orgasm.

I wanted so much to be assertive, but I always ended up going along with whatever the other people around me wanted because I craved acceptance. Shutting out Bob after his comments had been a mistake, but I still couldn't get my head around the idea of sex with men. I'd never thought about it before, and I wasn't attracted to men, but when they thought I looked sexy in the short shorts I was now buying from the juniors' department and wearing as a twenty-eight year old man, it was the biggest turn-on I'd ever experienced.

Bob had given me his phone number long before saying what he said and then leaving. There were many lonely nights where I almost called him, but always chickened out the way I had whenever I tried to call a girl from high school forward. I was always too afraid of saying something wrong or looking foolish.

The longer I spent time being lonely, at home and at work, and with no social life to speak of, the more I pushed the envelope in showing off my legs. One Saturday night, at probably two o'clock in the morning, I was in the apartment complex laundry room doing my laundry. It probably makes me look like a loser to admit it, but having no social life and being up most weekend nights playing computer games by myself, but I tended to do laundry late at night on weekends because no one else used the laundry room then.

I was wearing my most daring pair of shorts yet, a pair of black spandex shorts of the kind dancers and cheerleaders do warm-ups in, Blissfully going about my business, putting my clothes into the washer and putting in my quarters to start the load, I turned around to see two guys standing there.

When had they come in? I hadn't heard anything, but it was a fairly large laundry room and I was focused on putting in my laundry and not on anything else. They didn't appear to be doing any laundry. They just stood there and smiled.

"What's up?" one asked while chuckling.

"Just... um... doing laundry..." My voice was cracking and I was stuttering and couldn't help it. I was terrified, but at the same time my four inches rose to full attention.

"Nice shorts," the other said and they both started laughing.

I tried to deepen my voice and tell them I needed to get back to my apartment, but it came out like a whimper of, "I need... go..." and I couldn't finish the sentence because my teeth were chattering with fear.

"But you just started your clothes," the first guy said in a patronizing tone.

They were both dressed in t-shirts and sweatpants, looking like they'd been hanging out drinking and whatever, and just decided to come to the laundry room. They weren't doing laundry, and they kept stepping closer to me and cracking up with laughter as I kept nervously stepping back. I was shaking like a leaf and couldn't stop whimpering and making no effort to escape.

They had backed me against the back wall of the laundry room, out of sight of the windows and the door, so no one could see I was in distress. Were these guys going to beat me up? I put my hands up meekly in front of my face and whimpered out, "Please... don't... hurt me..."

"Aw, sweetie pie, we don't want to hurt you, but we might. You know?"

"Please... don't... I'm... sorry..."

"What are you apologizing for, hot legs? Did you do something bad?"

They were laughing at me and I didn't know what to do. I was squirming, fighting back tears, and basically being a pathetic excuse for a man, especially given that I was wearing tight black spandex short shorts.

"Nah, we were kind of hoping you'd suck our dicks," the second guy laughed as I started to lower my hands away from my face.

"Wh-wh-at?" I stuttered out in shock.

They both dropped their sweatpants as I cowered in the corner, a deer in the headlights expression on my face. I swallowed hard as they got closer, no longer wearing any pants or underwear, and very tentatively lowered my gaze down to their semi-hard cocks, swinging there just inches away from me, while the two guys just grinned and said, "Come on, sweetie, you know you want it."

"Oh... god..." I cried out hoarsely as tears began streaming down my face and I very willingly knelt down in front of the two men, my knees on the hard concrete floor. The tears flowed as I look up meekly and said, "I... I... never... done... before..." and slowly reached for their cocks, which were now stiffening up impressively.

"Well, sweetie pie, if you're gonna keep walking around in shorts like those with legs like you got, you're bound to end up sucking cock sooner or later."

"Have to start somewhere," laughed the second guy as he grabbed his cock at the base and smacked me in the face with it. "Come on, pretty legs, you have to start sometime."

It was like I'd suddenly discovered my place in the world. After all my struggles to be assertive and speak up for myself, my inability to get a girlfriend, being a virgin well into my twenties, and having no real friends, it was strangely comforting to be on my knees in front of other, stronger men, doing as I was told.

When I had my first taste of cock, tentatively kissing along the shaft of the first guy's now completely erect nine inches of serious man meat, I gasped and sighed, and was then helpless to keep myself from engulfing the entire mushroom head with my lips while letting out a moan.

It may not have been how I wanted my first time to go, but it was how I needed it to go. After all, I was the shy, solitary kid who was afraid to speak up in class and would have been invisible if it weren't for the fact that I shaved my legs. I paraded my shaved legs in front of men, dying for their attention, craving compliments, and I did all this while barely able to speak above a soft mutter and almost always stuttering when I tried to talk to someone who I saw checking out my legs. I needed someone to take charge and put my down on my knees. Bob wasn't going to take the initiative and I was much too scared to assert myself when I didn't know what I was doing. If I couldn't be assertive enough to speak up for myself when I was getting bullied and teased, how could I assert myself even a fraction of what it would take to put a cock in my mouth for the first time without being made to.

At first, I trembled and sobbing, having my head moved back and forth between the two cocks, having my mouth jammed up against their balls and being told, "Like and suck, faggot," and I did as I was told. I cried mostly because I didn't have the balls to stand up to these men or even resist them in the slightest way. I was too afraid to upset them and then have them hurt me as I cowered and whimpered the way I always did throughout school when I was the favorite target of so many bullies.

At some point, something in me snapped and I stopped caring that I was being made to do this and that I just gave in. I realized I was loving the way these big, juicy cocks felt against my lips and filling my mouth. They tasted and felt so good to me as they slid back and forth in my mouth and against my tongue. My eyes were rolling back into my head because I'd never felt ecstasy like this before. How had I gotten to the age of 24 before even realizing I not only liked sucking cock, I loved sucking cock.

With these guys, it really didn't matter how scared, inexperienced, or passive I was. They would just grab my head and put it where they wanted it. They laughed at me, ridiculed me, and called me every name you can imagine. It was humiliating, but I was realizing that I loved being humiliated, degraded, and exposed for what I really was. I loved that sucking cock made me cry while at the same time making my little penis rock hard.

They were working me so hard, and I was crying so much, that after only a couple of minutes of their relentless fucking of my incredibly willing mouth, all I could see was stars, and then the only thing I could feel or think about was how good those cocks felt, pushing into my mouth as I drooled and slobbered. It felt so good and so right.

When they came, I could feel them tense up, and while the first surprised me by ramming his cock down my throat and forcing me to swallow as I struggled to breathe through my nose, I was eager to do better when the second man tensed up and pulled my head down forcefully.

By the time I could see the room around me again instead of the blur of my tears and the stars of my moment of total ecstasy, I was curled up on the floor, my body shaking, as the full realization of what I'd done hit me. I felt like I couldn't move, I was terrified and weeping at the thought of finishing my laundry and going back to my apartment. It had to be at least an hour that I lie there, curled up like a baby, a pathetic excuse for a man, with shaved legs in spandex shorts, drool and cum still dripping from my mouth.

It was my fear of being discovered like that which finally caused me to shakily get up on my feet, finish my laundry, and attempt to go back to my apartment without being seen. When I got home, I just threw my laundry basket on the floor and collapsed on my bed in tears. I had no one to call, no one to talk to, no friends or family, and I was feeling so alone as I struggled with the realization that I loved sucking cock. I wanted to be a regular guy. I wanted to learn to stand up for myself and to speak up when I needed to. The last thing I wanted to be was a cocksucker, but that was exactly who I am.

My knees were rubbed raw from being on the concrete floor while I sucked off the two strangers. I put Band-Aids on them and wore pants for a week while they healed, but then I couldn't escape the temptation to put on my short shorts and show off again. I looked for Bob, but didn't see him anywhere, and then, in my most pathetic act yet, I started hanging around the laundry room late at night hoping to run into them again and to suck their cocks again.

As much as I didn't want to admit that I was, at heart, a cocksucker, as defined by someone who loves to suck cock, I was walking around in short shorts late at night hoping to be forced to suck again. It was all I could think about, at work, at home, and especially when I was flaunting my smooth, feminine legs, so long and shapely, out in public. We won't even get into how furiously I masturbated at home while wearing a miniskirt and high heels. I'd started collecting sexy women's clothes, especially those that would make my legs look even more feminine if I managed to have a man over to see me dress up for him.

I was both frustrated and confused. There I was, pretending to have a reason for going down to the laundry room, pretending to check dryers for something I'd lost, wearing tight short shorts and hoping to be noticed. At the same time, I was terrified that someone would see me, and I kept wishing that showing off my legs wasn't something that thrilled me. I kept wishing I hadn't enjoyed going down on those two strangers, and I kept wishing I could stop thinking about how much I wanted more.

One night, I was walking back from the laundry room when a truck began driving very slowly behind me, and then alongside me. I looked up sheepishly to see a strong looking man, with his bicep up against the truck door as he leaned over and said with a smile, "Nice legs."

I'd never been so terrified in my entire life. Whenever a man said something to me about my legs in short shorts, my first thought was that he thought I was a woman. My second thought was always that he'd kick my ass, either because he realized I wasn't a woman or because that was his intention from the start. Growing up constantly bullied, that was just was I always expected from any encounter with a man.

My mind locked on trying to decide whether to run to my apartment or to freeze in terror, so I ended up staring blankly at Mike as he idled his truck alongside me not knowing how to react, and so I barely reacted at all.

It wasn't just terror that froze me, it was that my mind remained mired in conflict. All I could think about was how much I'd enjoyed being made to go down on those two men in the laundry room, except I wanted so much to live a regular life like everyone else with a girlfriend and eventually a family. How was I going to do that if I went around showing off my legs, dressing up for men in miniskirts and high heels, and giving them blowjobs?

What one wants is often difficult to accept, especially when the one thing you want more than anything else would make it impossible to have the other things you want. For me, if I gave into my desire and accepted it as something I needed, I'd never meet a girl and fall in love or any of that.

"I'm Mike," the man in the truck told me, then adding with a tone of concern, "Are you okay?"

"Huh? What? Oh... yeah... I was just... I don't..."

"Let me park the car and we can talk," Mike said with a smile before pulling his truck into an open parking space. I just stood there in disbelief, unsure of what was happening, but it didn't seem like he meant to hurt me. His voice was too calm and reassuring.

When he got out of the truck and walked over to me, I was still standing still, staring into space.

"What's your name?" Mike asked me as he stepped onto the sidewalk next to me.

My teeth were chattering and my lips visibly quivering as I stuttered out, "I'm... uh... Keith... no... sorry... I just..."

"Nice to meet you Keith," Mike said with a calm smile, acting like I'd answered normally instead of in a nervous stammer.

"I... need... get... home..." I was straining to talk in a strong, confident voice, but it completely eluded me and now my knees wee shaking.

"Which way? I'll walk with you."

"You... I mean... you... don't... have... to..."

"No, it's fine. Lead the way." After I did and he started walking behind me, Mike added, "Look at that cute little butt you have."