I Used to be Pathetic

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Keith's first time scares him a little bit.
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KaseyLegs
KaseyLegs
358 Followers

I remember it well, some 25 years ago, when a woman who had been a friend of mine for many years, who knew I lusted after her but had always rebuffed my advances, found out that I shaved my legs, painted my toenails, and pranced around in miniskirts and heels.

She'd stayed at my apartment the night before, sleeping in my bed while I crashed on the couch. In the morning I saw her in my closet, looking in the back where I hid my "girl clothes" and saying, "I was wondering about the ladies' razor in the bathroom. Keith, do you shave your legs? Let me see."

I was excited when I relented and she gushed about how I had legs like a girl and any woman would "kill to have legs like that." I blushed, repeatedly asked her if she was serious, and she complimented me more.

On my birthday, about two months later, she told me she had a surprise and invited me to her house. She had two of her friends with her, Chris and Rachel. I had met Chris before, she was always nice to me, but had never met Rachel. Marci told me Rachel was going to do a makeover for me and that they'd bought me a new outfit.

It was the first time I'd ever gotten completely dressed up, with breast forms and makeup, and my hair done in a feminine style, and showing off in front of Marci, Rachel, and Chris was a huge turn on. For the first time ever, I was glad I didn't have a big cock because I had such an erection strutting around in front of them like that.

Gary had just walked into the house. I'd never met him before, but at that point I'd had quite a few drinks and had smoked a joint with Chris, and I was joyfully prancing around in a miniskirt and heels, all made up like a woman. When I turned around and saw him standing there, leaning against the wall, his arms crossed, smiling at me, I froze in panic.

I'd never anticipated a man showing up to the party, although Marci hadn't said anything about anyone else coming, but I hadn't asked. When I found out the surprise was a makeover, I couldn't resist going for it, especially with three attractive women urging me on.

"You are one sexy faggot," he said with a laugh as I stood there with a deer in the headlight look on my face.

"I'm not..." I said, in the meekest and most pathetic voice imaginable. I could barely eek out the words.

"Oh, I don't know, guy with legs like that belongs on his knees. Don't you think, Keithy?"

"No... I just... like to... dress up..." I stammered.

Gary stepped towards me. As I stood there, shaking nervously in my high heels, he stroked my face and said, "You know, they say guys who like to dress up give the best head."

"I've heard that," chimed in Rachel, who was giggling while Marci and Chris just grinned from ear to ear.

Gary brought my face, with my jaw trembling and my body shaking, up to look at him before he said, "Kneel for me, sweetie. I've already got a boner just looking at you."

Tears were forming in the corners of my eyes and I couldn't stop shaking. I tried to again insist this was all wrong, but instead I stammered out, "Okay," and as Gary held my arm so I didn't fall as I went to kneel down in front of him while wearing heels and shaking as much as I was.

"See, I knew he wanted it," giggled Rachel. "This is hot as fuck!"

"I'll make popcorn," Chris told the others before getting up and going to the kitchen.

Tears flowed down my face as I knelt there, looking up each time Gary barked at me to keep looking up at him as he kicked off his shoes, unbuckled his pants, unzipped his pants, and pulled them slowly down and off.

"Show us what a good cocksucker you are," Gary told me sharply. "Don't be afraid, put your hand around it, faggot."

"Yes, sir," I said as my trembling hand moved towards his rock hard, nine inch cock, and my tears were joined by drool that came out of the corner of my mouth. I was overcome and cried out as I coiled my fingers around his cock, "Oh god, I want it so much."

Maybe it should have always been obvious to me. Not only did I have a girl's legs and build, I'd lived my life with a dick for which it would be generous to say it was four inches when rock hard, and thin as a lady's pinky finger. I'd slept with two women at that point, and I was 28, and with one of them only once and the other three times. With my timidity combined with that and what one of those women called "baby balls," it wasn't like anyone was lining up for that action.

I remember taking Gary's cock in my hand and how good it felt, so warm and hard, such a beautiful piece of meat, but I don't remember putting it in my mouth the first time. All I remember was feeling it sliding between my lips and how incredibly satisfying that was. When he hit the back of my throat and I gagged, with the girls laughing, my little boner popped free of my panties and out from under my miniskirt with copious amounts of precum dripping from it.

"Put that away," Gary snapped as I recoiled and he redirected my face up at him. "No one wants to see that shit."

"Seriously, what IS that," laughed Rachel McGiggles.

I felt so humiliated and degraded, but that only intensified how much I enjoyed sucking Gary's gorgeous cock while dressed like that. I said all kinds of things whenever I took a breath from sucking. "So good, so good," was the most frequent. When he came on my face at the end, I moaned out so loud they could have heard me in the next apartment.

"Damn, you really needed that, didn't you, Keith," Marci laughed at the end.

"That was some good live action porno," Rachel added as I remained on my knees, looking sheepishly away from the audience, feeling ashamed of what I'd done and how I'd so easily lost control.

I struggled to get up, well beyond embarrassed, and stumbled out of the room in my heels, one of the straps getting tangled and me slipping and falling on the way out.

"Don't trip, sweetie," Rachel said with a catcall whistle.

I ran into the bathroom and locked the door. I quickly tried to wash my face and clean off all the cum and makeup, and then change back into my regular clothes so I could get it my car and get out of there.

I was sobbing out loud and falling apart as I tried to find the clothes I had left in the bathroom when I started the makeover. I was in a panic when Marci knocked on the door and said, "I have your clothes."

I tried to brush away my tears and open the door as Marci held out clothes that weren't mine. It was my sneakers, socks, and blue t-shirt, but instead of my long pants, there was a pair of Daisy Dukes.

"Remember when you used to try to get me to wear short shorts all the time after you saw me in shorts like these at the lake a few years ago? Well, now I want you to wear them and you can drive home like that, can't you, cocksucker Keith? I mean, you are a cocksucker who gets off on showing off his legs in heels, so you might as well stop hiding the fact."

Marci was openly mocking me and I stood there and took it, trembling and just wanting to run away. I grabbed the clothes and put them on, feeling ridiculous in such short shorts, with my ass cheeks peeking out, but I was just going to run out to the parking lot, get in my car, and go back to my apartment and try to get across the parking lot there without being seen.

I had hoped that maybe I had a pair of sweatpants or a spare pair of pants of some kind in my car, but then I figured I would do just do it. I wanted to get out of there and away from the humiliation, but then my car broke down halfway home, on a road without a lot of traffic, without any stores or businesses nearby.

My choices were to walk several miles in search of a phone, as we did not enjoy the luxury of cell phones back then, or to wait in hopes that someone would stop by. I decided to wait, mostly because I did not want to walk for miles dressed like I was, unable to get the imagine out of my head of me sucking Gary's cock.

I would wait in the car with my flashers on until someone came by. When I heard them coming down the road, I would step out and try to flag them down. It was five cars before someone stopped, and that was two guys who thought I was a woman because of my long hair and how I was dressed, and when they pulled over to help and saw me, with evidence of makeup still on my face, looked harried and weepy.

"What the fuck?" one of the guys said. "You aren't abroad."

"Fucking hell," said the other as the both stopped and stared at me as I just froze with images in my mind of having sucked Gary's cock flashing through my mind.

"Eh, we'll give him a ride, eh Jimmy?" said the first guy after a moment of seeing me standing there shuddering. "What d'ya think?"

"What the hell, why not," snickered Jimmy. "Come on pretty legs, we'll give you a ride to the gas station."

I'd already endured so much humiliation and my own loss of control that evening, so everything felt like it was heaping on more of the same. I tried to tell myself they might be laughing at me, but they would just drop me off, and then I'd have to deal with standing in a gas station talking to a mechanic the way I was dressed.

Then, Tony, the second guy, got in the back seat with me as Jimmy got behind the wheel. I went to go around, saying, "I'll get in the front," weakly, but Tony grabbed my arm and said, "No, no, this is perfect," and began unbuttoning his pants. "You suck a good cock, pretty legs?"

My head descended with remarkable ease. It always has when I've had a hard cock put in front of it, but I was only beginning to accept this. They pulled over and took turns in the back seat with me, took my wallet and keys, and pushed me back out onto the road and drove off.

I'm not pathetic any longer, but I was for a few years because I was unable to accept that what Gary said was true. I do belong on my knees in front of men, and I had to admit that and admit that nothing felt better than feeling that cock slide into my mouth the first time, except maybe when I took it up the ass the first time.

Bob was probably the only man I've ever been with who had respect for me, both before and after I sucked him off. He treated me with kindness, and he begged to let him fuck me, even as I insisted I'd never done it and had no interest in it.

One night, he convinced me to try, and while I expected it to be painful and difficult, my asshole was remarkably prepared to take cock with ease and as often as I've been fucked over the past 25 years, it has remained amazingly tight. Every man who fucks me loves the way that hole feels. It was more eager for cock than my mouth was.

But, as I said, I'm not pathetic any longer. I do my duty, I suck men who get hard looking at my legs, and at 53 I still have gorgeous gams and I still love showing them off. I can tell now when I'm turning a man on when I see him checking me out in my beloved Daisy Dukes at the supermarket. They know there is only one reason why a guy in his 50s is walking around in short shorts with his legs shaved, he's real desperate for dick. I think we all know that.

And I now admit it, I prance around like that looking for attention from men in the hopes of finding a fan I can give a nice long, hot blowjob to, so I'm not pathetic any longer...

KaseyLegs
KaseyLegs
358 Followers
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AnonymousAnonymous12 months ago

I have sucked a few cocks in my day but never had the guts to go out into public dressed like a slut or sissy even though I have always wanted to. I have come to terms that I am a cock sucker for Men. Now I have to get my small balls up to go out and get more cocks to suck. I love dressing like a slut. BIP

AnonymousAnonymousover 4 years ago
Hi Kasey

It’s me Barbara - my old email is defunct and my new one is fairyboy65@gmail.com

Hope you get this and reply soon xxx

AnonymousAnonymousalmost 5 years ago
Much Younger

I was younger when my Sissy personality emerged. I was 18. It started when I began taking my sister who was 12 years younger (my slutty mom got knocked up by her boss when she thought she was too old to get pregnant at age 40) to dance lessons twice a week. The woman who was the owner of the dance school (Phyllis) noticed my legs. One day she took me aside and said, "follow me." She took me into her office and said,"You have really great legs and there is someone I want you to meet next class." The next trip to the dance class, Phyllis took me to the office immediately and introduced me to "Harriet" who was one of the stars of the female impersonator review on the strip. Harriet and Phyllis had me undress and took measurements of my body. Harriet was thrilled I had such a small waist. I came to the studio Sunday and they shaved and made me up. I was shocked when I looked in the mirror, I was beautiful. Harriet then took me to the club and I watched the review. Then I was told to go sit at the bar and mingle with the customers. A middle aged man with all gray hair came up to me and said, "I just paid for a trip to the VIP room with you." He took my arm and escorted me to the door marked VIP and we went in. It was maybe 6 by 8 and had a couch. The guy quickly dropped his jeans and shorts and in his best ex Marine voice barked, "Kneel". I did and just seconds after my knees hit the carpet, his cock was at my lips and he said, "Suck me." I opened my mouth and his cock was shoved all the way in and I gagged but closed my lips around his cock and began sucking and he began shoving his cock in and out. He lasted about three or four minutes and when he was ready to cum he grabbed my head and said,"You better not lose a drop, swallow it all." I swallowed all his cum. I have been dressing as a woman and swallowing cum for 40 years!

AnonymousAnonymousalmost 5 years ago
CD Turn ons

Acceptance, ah yes the eventual acceptance of my place in life is much like yours! I didn't have GFs or even BFs that helped me discover how much I enjoyed kneeling for men or, like you, spreading my legs later! I admit that the first few times I ran and cried and berated myself for ever doing such things yet always wanted more.

Now I have come to accept my lot in life as a Sissy it does not mean that I have lost the shame of being out shopping, or even just walking around in hopes of being used, while dressed like a slut in short skirts or dresses that display my nylons' and the garter straps holding them up! It doesn't remove the stigma of what I feel when I bend down to display my panty clad buns to everyone close enough to see me.

It is not that I am any less pathetic, just that I am more accepting of openly displaying my need and desires to be used by other men for their pleasure!

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