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“You stiffen up at the thought of being Sarah, don’t you?” he said, tossing the black padded bra on my cock. At that point, I realized there is no turning back, I finally worked up the courage and I’m ready to please my first man as Sarah. And for the record, I never pleased a man before. It only excites me to do so when wearing female clothes.
Let me introduce myself. I am not the flamboyant guy next door, or the one who’s always at the cool parties in town. I am a very ordinary guy, works in IT, and that’s it. I must say I am good looking, slim shaved body, and nice thick cock. At 27, I get quite a lot of action with girls of all ages. Since my teenage years, the best part about exploring a girl was her panties. Plain and simple. The cuter, the better. Forget all the slutty thongs, or crotchless panties. Cotton bikinis and girlboxers are my kind of underwear, especially patterned or printed ones. Rubbing a girl through her panties, licking her through the soft material, biting on her shaved pussy lightly always got me hard in an instant. On buses, at school, in clubs, I used to wonder what panties the girls had on, trying to link panties to a particular girl according to her looks and manners.
The first girl I fucked had a yellow thong on, a frilly see thru one. She was a foreigner, we were both drunk after a party. I was excited about my first fuck just like all the other guys, but I remember gripping on her tights, satisfied that I managed to make her keep her undies on. Since then, fucking a girl in panties has been my major turn on, even if the panties are destroyed in the process.
One of my earliest fetishes was that of asking a girlfriend to give me her panties after we finish, but always ended shying out. Daniela was extremely open, loved sex, bisexual and hated sucking cock. Fine by me, our fucking was to die for. She only wore girlboxers, bright, colourful stretchy ones. After much planning, followed by a good drilling, I asked her to go home without her panties. I am sure she was wet of the train, feeling all exposed. Her white boxers, with red waistband and strawberries printed casino şirketleri all over were hugging my cute perky ass before she was at the train station. Stiffing up immediately, I put on some porn, and it hit me. Usually, the partner in cute panties is the one to be penetrated. The bigger the cock, the better. I remember gulping at the sight of a cute blonde taking it up her ass as I cummed in Daniela’s panties. And believe me, that wasn’t the last time that happened.
Time passed, girls came and went, leaving the occasional panties at my place, sometimes even more. The more porn I saw, the more I was eying the cock and wanting to be the girl. The search bar history mostly read “older and younger” “older and teen” “teen in panties” and the like. I developed a crush on older guys. 60 and over, skinny ones with a huge, thick cock, who loved slightly fem guys in cute panties. Older daddies giving a spanking on some pantied ass. As I said, I am quite shy, but as soon as I slide panties on, I just felt so girly and willing to please. I started going into chatrooms behind my girlfriend’s back, toying around with various girly names. Samantha. Cassie. Nicole. I realized that men only wanted one thing. To fuck me.
The internet also provided another option to fuel my ever growing fetish. Online shopping. Not just panties. Bras, AA padded ones. Skirts, short and, again, patterned. Tights, black opaque ones. Crop tops. I always went for an average, next door girl look. I started to dress up every day, the desire of meeting an older man for the first time growing stronger. I tested my luck via Tinder. It worked within hours.
John lived 15minutes away by walk. 53, divorced, blonde and smooth. So my type. We were both at work when we matched, and things escalated really quickly. He had a way with chatting. He was saying how he would treat me, first gently, cuddling, kissing, the peeking under the skirt, and the rough stuff. I felt ready to be pushed on all fours, skirt hiked up, tights down, panties just below my hole, and banged like a slut in heat. Even without a condom. But before that, casino firmaları I would drop on my knees, taking in my first cock, as I rub my nipples through the bra. I am flat chested, and if I were to have boobs, I want them small, so some good padding would do the trick. I was ready. Being at work, in a suit, I felt girlier, and hornier than ever thanks to John.
We agreed on meeting in a couple of hours. I rushed home, shaved completely, but didn’t shower. John said he love the musky smell of a young man as much as he loves gender bending. I started picking out the clothes and yes, that was hard. Which panties am I gonna suck my first cock in? Which bra makes me look cute and slutty for the first time? I asked John for advice, and he asked for a full nude selfie. I obliged. Naked, looking down on my slim pale body, I waited for an answer. The message contained one word. Black. I decided on a plain black bra, black miniskirt which enhanced my cute perky ass, a purple crop top, black opaque tights..and colourful girlboxers. I couldn’t wear plain black ones. Not for the first time. Either shocking pink ones with S-L-U-T in black on the back, or a zebra print one with pink lace trimmings. I opted for the latter, fearing the first one was too much. I packed it all in a bag, and headed out.
Door 7A. I ring the bell. No answer. I ring it again. John opens, adjusting his glasses. He is bare chested, wearing only a pair of shorts.
“Do come in. Remind me, Sarah?”
He grabbed my ass hard when I walked in. Hard.
The smell of aftershave hit my nostrils. Manly aftershave. Yes, Sarah. That was the name I felt like being called that day. I followed him, he leading me into a well kept apartment and into a huge bedroom. Double bed in the middle. I gulped, looking for the ensuite bathroom so that I can go in and change.
John took my hand and made me sit next to him. We cuddled. He went in for a kiss, I turned my head. Second time, our lips met and my jeans went down. John’s hand was rushing over my body, I could sense his emergency. He gasped for breath, urging me to strip. I started güvenilir casino doing so, trying to be provocative, hoping all those porn movies stuck in my mind and I’m showing off. Teasing an older cock. As I wiggled my ass for him, in the mirror we make eye contact. One hand was in his shorts, the other fiddling round in the bag I left at his feet. Once I undressed completely, he eyed me. I felt ashamed, blushing slightly.
“Come next to John, Sarah”
He pulled out the bra, putting it on my chest. He tossed it on my cock and said my girly name in the sexiest manner possible. Seconds later, he pushed me on the bed, straddling me, his sharp teeth on my left small nipple. He bit me hard, I felt like crying. Same sharp teeth goes on the right one. Purple marks left all over, as John exposed himself. Fuck, it’s much bigger than it looked in the picture. John’s tone is getting more aggressive, more agitated. He urges me to put the black bra on. I get up, put it on, hook it up expertly.
“Ok, that’s enough Sarah. Please this cock”
I dropped on my knees, horny as fuck. Before I had a chance to go for my panties, since of course my fetish included me being in them, John forced himself in my mouth. I took it in, using my tongue to please the head. Soon my mouth was filled with cock and John’s strong thrushes was making my head bob like never before. I rubbed his balls and legs as I sucked the best I could, hearing him moan loud. Pulling me out from my short hair, he grumbled about me not having longer hair or a wig on, and cummed on my cheek. A huge, thick load of cum. Some dripped on my lips and mouth, and I licked it, tasting another man’s cum for the first time. It was so salty. Smiling, John handed me some tissues, which I used to wipe all that sticky cum off my cheek.
“Ok Sarah, that was good. Out now, I want to watch football. Don’t forget your clothes”
At home, in bed, the feelings were extremely mixed. Two things kept resurfacing. One, John should have had that attitude while splitting me in half with his cock, only me being fully dressed. Secondly, as I was walking out, I saw a photo of John hugging a girl my age.
The sharpie marker and the new lacey girlboxers made up for the disappointment that night, but secretly I wished that John would get in touch again, ideally when the football season is over.
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