Not long after I got out of the service, I met Trish at a house party. She was a hot little brunette with a great body and we hit it off right away. After a few months of dating we ended up moving in together and she was a great lover...with one little quirk. She always wanted me to wear a pair of her panties while we were having sex. I readily obliged because she was so good on her back and also gave the best blow job I've ever had.
I got used to wearing her underwear and have to admit that I looked and felt very sexy in them. She wore very feminine sheer nylon bikinis, some trimmed with lace, ruffles and bows in every color you could imagine.
It wasn't long before I would go directly to her pantie drawer when she was gone and get a throbbing hard on while exploring her silky things and deciding which of them to wear. As I pranced around the house in her panties, I found myself swinging my hips and putting a little wiggle in my walk, loving the feel of my little cheeks jiggling in the snug nylon fabric that was caressing my ass. My favorite thing was to end up in the bathroom in front of the full length mirror, turning around and jacking off while looking at my ass covered in lace. I realized that I had a very fem little fanny and would start to cum after just a few strokes while looking at it.
I started to imagine how sexy it would be to let another guy see how nice I looked in her panties and maybe even let him watch me stroke my seven inches while wearing them. I looked so much like a girl from behind and with a little practice, I knew I could wiggle my ass as well as any of them and I wanted to show it off. That's when I knew I wanted to wear more than just her panties. It got to where I could hardly wait for Trish to leave the house so I could try on some of her other things.
I found that I could fit into most of her clothes, though they were a little snug. I liked the feeling. I'm slender and pretty leggy at 5'10" and 153 pounds. I could wear most of her lingerie, bras, hot pants, skirts and even a couple of her summer dresses but unfortunately, my feet didn't fit in her heels and her pantyhose were too small. I knew I would take care of that at some point because the thought of slipping into a pair of high heels wearing sheer nylons and a short-tight skirt made me tremble with excitement.
Anyway, we were together for almost a year before we broke up for a variety of reasons. She stayed in the house we were renting and I moved out, but not without taking a few selected items from her lingerie and panty drawer. I wanted to continue cross dressing and wasn't sure how I would be able to come by sexy things on my own. However, over the next few months I did muster up the nerve to buy things I liked at stores in the mall, adult bookstores, on line and even garage sales, which to my surprise offer a lot of women's clothing.
Going out in public wearing feminine things under my 'straight' clothes was exciting for me and eventually became the 'norm. I always wore a pair of lace panties and often a bra, garter belt and nylons or sheer pantyhose.
Anyway, I hadn't seen Trish for six or seven months until one night I went out for a beer at the neighborhood tavern. I was wearing a skimpy pair of red bikini panties trimmed in white lace, the matching bra, a loose fitting button down shirt, snug white jeans and sandals.
And there she was, sitting at the bar with a guy. There were only a few patrons in the place and I thought about turning around and leaving, but I was thirsty and took a seat at the end of the bar. I had just ordered my beer when she noticed me.
"Hi Tommy, how are you?" she called out. "Why don't you come down and sit with us. Let me buy you a drink."
I just waved at them as my beer arrived and took a nice long drink of it.
"C'mon down here Tommy. There's someone I want you to meet," she insisted.
Reluctantly, I grabbed my beer and walked over to them, pushing a bar stool aside and leaning on the bar next to what I guessed was her new boyfriend.
"Tommy, this is Dan. Dan, this is Tommy, a new friend of mine," she said as she introduced us.
We exchanged an awkward handshake and I took another pull from my frosted mug. He was handsome, fit, dressed casual and smoking a cigarette.
"So, how have you been?" Trish asked with a bit of a slur.
It appeared they had been there for a while. She never did hold her booze very well.
"Doing fine," I replied. "Just stopped in for a quick cold one."
"It's nice to see you again." She leaned toward me and asked," So tell me, do you still wear panties?"
I blushed and took a swig of my beer as Dan turned to look at me.
"Well, uh. That's kind of personal Trish," I stammered.
She grabbed Dan's arm and began talking rather loudly, "He looks so hot in my panties, you wouldn't believe it! His little ass is so cute!"
I was embarrassed and getting ready to leave when Trish excused herself and headed for the bathroom.
Dan waved to her vacant stool and said, "Why don't you sit down and let me buy you another beer?"
I took the seat and after our drinks came, he scooted closer to me and rested his hand on my knee.
"So, you didn't answer Trish's question. Do you still like wearing girls panties?" he asked, inching his hand closer to my crotch.
I couldn't believe he was coming on to me right in the bar but it felt good and I was horny. I spread my legs a little, letting him know I liked it.
"And what color panties are we wearing tonight?" he asked, moving his hand up my thigh.
"Uh... they're red," I mumbled. Then without thinking added, "Lace bikinis."
He pulled his stool closer and rested his hand directly on my cock, then whispered in my ear, "A guy in panties makes my nine inches rock hard, and I'm getting there right now."
I reached down and brushed my hand across the big bulge in his jeans, looking around to be sure nobody was watching. "Yes, I can see that. I bet Trish has fun with this."
"Yeah, she does and you can too, baby. I know you like it. Can I call you sometime?"
He was making me so horny I was nearly breathless.
"Yes, you can call me," I murmered.
I stood and asked the bartender for a pen. While I was leaning over the bar writing my phone number on a napkin for him, he reached down and caressed one of my ass cheeks, gently kneading it with his hand.
"Oh yes, this is nice." he whispered. "You really do have a nice little ass, sweetie."
I turned to face him and looked around. The two guys at the far end of the bar were involved in their game of pool and the bartender was washing glasses with his back to us. I stuck the napkin with my phone number in the pocket of his jeans, making sure to brush my hand over his stiff cock while I did. One hand still on my ass, he pulled me closer and put his other hand on the front of my jeans and started massaging my lace covered cock, basically jacking me off with my pants on right there in the bar. I let out a whimper and he knew I loved it.
I rested a hand on his shoulder, leaned down and whispered in his ear, "Danny, you're going to make me cum right in my panties if you don't stop it."
"That's a good girl," he said, as he worked his hand faster and faster across the front of my jeans.
"Soak those pretty little red panties for me right here.
I got used to wearing her underwear and have to admit that I looked and felt very sexy in them. She wore very feminine sheer nylon bikinis, some trimmed with lace, ruffles and bows in every color you could imagine.
It wasn't long before I would go directly to her pantie drawer when she was gone and get a throbbing hard on while exploring her silky things and deciding which of them to wear. As I pranced around the house in her panties, I found myself swinging my hips and putting a little wiggle in my walk, loving the feel of my little cheeks jiggling in the snug nylon fabric that was caressing my ass. My favorite thing was to end up in the bathroom in front of the full length mirror, turning around and jacking off while looking at my ass covered in lace. I realized that I had a very fem little fanny and would start to cum after just a few strokes while looking at it.
I started to imagine how sexy it would be to let another guy see how nice I looked in her panties and maybe even let him watch me stroke my seven inches while wearing them. I looked so much like a girl from behind and with a little practice, I knew I could wiggle my ass as well as any of them and I wanted to show it off. That's when I knew I wanted to wear more than just her panties. It got to where I could hardly wait for Trish to leave the house so I could try on some of her other things.
I found that I could fit into most of her clothes, though they were a little snug. I liked the feeling. I'm slender and pretty leggy at 5'10" and 153 pounds. I could wear most of her lingerie, bras, hot pants, skirts and even a couple of her summer dresses but unfortunately, my feet didn't fit in her heels and her pantyhose were too small. I knew I would take care of that at some point because the thought of slipping into a pair of high heels wearing sheer nylons and a short-tight skirt made me tremble with excitement.
Anyway, we were together for almost a year before we broke up for a variety of reasons. She stayed in the house we were renting and I moved out, but not without taking a few selected items from her lingerie and panty drawer. I wanted to continue cross dressing and wasn't sure how I would be able to come by sexy things on my own. However, over the next few months I did muster up the nerve to buy things I liked at stores in the mall, adult bookstores, on line and even garage sales, which to my surprise offer a lot of women's clothing.
Going out in public wearing feminine things under my 'straight' clothes was exciting for me and eventually became the 'norm. I always wore a pair of lace panties and often a bra, garter belt and nylons or sheer pantyhose.
Anyway, I hadn't seen Trish for six or seven months until one night I went out for a beer at the neighborhood tavern. I was wearing a skimpy pair of red bikini panties trimmed in white lace, the matching bra, a loose fitting button down shirt, snug white jeans and sandals.
And there she was, sitting at the bar with a guy. There were only a few patrons in the place and I thought about turning around and leaving, but I was thirsty and took a seat at the end of the bar. I had just ordered my beer when she noticed me.
"Hi Tommy, how are you?" she called out. "Why don't you come down and sit with us. Let me buy you a drink."
I just waved at them as my beer arrived and took a nice long drink of it.
"C'mon down here Tommy. There's someone I want you to meet," she insisted.
Reluctantly, I grabbed my beer and walked over to them, pushing a bar stool aside and leaning on the bar next to what I guessed was her new boyfriend.
"Tommy, this is Dan. Dan, this is Tommy, a new friend of mine," she said as she introduced us.
We exchanged an awkward handshake and I took another pull from my frosted mug. He was handsome, fit, dressed casual and smoking a cigarette.
"So, how have you been?" Trish asked with a bit of a slur.
It appeared they had been there for a while. She never did hold her booze very well.
"Doing fine," I replied. "Just stopped in for a quick cold one."
"It's nice to see you again." She leaned toward me and asked," So tell me, do you still wear panties?"
I blushed and took a swig of my beer as Dan turned to look at me.
"Well, uh. That's kind of personal Trish," I stammered.
She grabbed Dan's arm and began talking rather loudly, "He looks so hot in my panties, you wouldn't believe it! His little ass is so cute!"
I was embarrassed and getting ready to leave when Trish excused herself and headed for the bathroom.
Dan waved to her vacant stool and said, "Why don't you sit down and let me buy you another beer?"
I took the seat and after our drinks came, he scooted closer to me and rested his hand on my knee.
"So, you didn't answer Trish's question. Do you still like wearing girls panties?" he asked, inching his hand closer to my crotch.
I couldn't believe he was coming on to me right in the bar but it felt good and I was horny. I spread my legs a little, letting him know I liked it.
"And what color panties are we wearing tonight?" he asked, moving his hand up my thigh.
"Uh... they're red," I mumbled. Then without thinking added, "Lace bikinis."
He pulled his stool closer and rested his hand directly on my cock, then whispered in my ear, "A guy in panties makes my nine inches rock hard, and I'm getting there right now."
I reached down and brushed my hand across the big bulge in his jeans, looking around to be sure nobody was watching. "Yes, I can see that. I bet Trish has fun with this."
"Yeah, she does and you can too, baby. I know you like it. Can I call you sometime?"
He was making me so horny I was nearly breathless.
"Yes, you can call me," I murmered.
I stood and asked the bartender for a pen. While I was leaning over the bar writing my phone number on a napkin for him, he reached down and caressed one of my ass cheeks, gently kneading it with his hand.
"Oh yes, this is nice." he whispered. "You really do have a nice little ass, sweetie."
I turned to face him and looked around. The two guys at the far end of the bar were involved in their game of pool and the bartender was washing glasses with his back to us. I stuck the napkin with my phone number in the pocket of his jeans, making sure to brush my hand over his stiff cock while I did. One hand still on my ass, he pulled me closer and put his other hand on the front of my jeans and started massaging my lace covered cock, basically jacking me off with my pants on right there in the bar. I let out a whimper and he knew I loved it.
I rested a hand on his shoulder, leaned down and whispered in his ear, "Danny, you're going to make me cum right in my panties if you don't stop it."
"That's a good girl," he said, as he worked his hand faster and faster across the front of my jeans.
"Soak those pretty little red panties for me right here.
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Hurry, before Trish gets back."
It was all I could do to keep from shouting out loud as I started to cum. I had never gushed in my panties before and it felt wonderful as he continued to rub me while I creamed in them.
I was out of breath as I looked over my shoulder. Trish still hadn't come out of the bathroom, the two guys were still playing pool and the bartender was stocking the cooler. Nobody had any idea that Danny had just made me fill my little red panties full of cum.
I was still trying to catch my breath as I thanked him and made my way to the men's room to clean up.
By the time I got out of the bathroom Danny and Trish were gone. I had a couple more beers and by then it was around midnight. The bartender said he was going to close early because it was so dead, so I drank up and left.
As I walked out to the parking lot I noticed another car parked right next to mine. It was Danny. I walked over and stood beside his open window.
"What happened to Trish?' I asked.
"I took her home. She was falling asleep," he said, a little disgusted. "I was hoping she would take care of this for me, but she was too drunk."
That's when I noticed his hard cock sticking up out of his unzipped jeans like a monument.
"I thought maybe you could help me out. Besides I never did get to see the pretty underwear you're wearing."
I walked around to the passenger side of his car, got in and slid across the seat next to him, wrapping my hand around his stiff cock.
"Danny, you are so nice and hard! You can't drive around with this big hard on. It would be dangerous," I said as I began working my hand up and down on his shaft. I stroked his big cock for a minute or so then took his hand and put it on his cock, letting him jack off while I eased back and started to undress for him.
I slowly unbuttoned my shirt and slipped it off my shoulders, letting him see my hard nipples sticking out of the lacy material of my little bra.
"Oh yeah, baby, That's what I want to see!" he said as he began stroking his cock faster.
I kicked my sandals off, undid the snaps of my jeans and wiggled out of them, letting him see me in just my bra and panties as I moved closer.
He slid one of my bra straps off my shoulder, leaned down and started sucking my hard nipple as his hand found its way to my lace covered cock.
"Oh honey, your panties are still wet. That was so sexy that you came for me in your panties standing right at the bar!"
"I loved it Danny. You're the only guy that's ever made me do that and I want to show my thanks for it." With that, I pulled him up off my chest, wrapped my hand around his big dick and started slowly jacking him off as I whispered in his ear, "If you promise not to tell Trish, I'd love to give you a blow job, Danny. You have such a beautiful cock. I really want to suck it for you."
"Yes, yes... I mean, no, I won't tell her, I promise! Just suck it for me sweetie, right now, please!"
I slid back a little on the seat, leaned down and held his big cock up straight with one hand and rested my other hand on his thigh. I flicked my tongue around the head, tasting his precum, then opened wide and went down on him. He stiffened and moaned in delight as I took him into my warm mouth.
"Oh honey, that feels so good! You are such a sexy little cock sucking girl!"
My little panties couldn't contain my hard cock and I reached down to stroke it while I was sucking him off. That was when he turned the dome light on in his car, flooding it like daylight. I got off his cock and looked up at him in question.
"You look so hot in your bra and panties with your mouth full of my cock. I want to look at your cute little ass while you suck me baby doll. Get up on your hands and knees and show it off for me."
I was a little leery of having the light on, but did as he said. Up on all fours, I was just getting into a nice rhythm of sucking his big cock again when I heard a noise. I came off his cock, jacking him off with one hand and resting my other on his shoulder.
"What was that?"
"Don't worry about it sweetheart, just keep sucking. I'm really close to giving you what you want." With that, he put his hand on the back of my head and pushed me back down to his waiting cock.
As I took him back in my mouth I could tell his shaft was getting thicker and the head of it was swelling. I knew I was going to make him cum soon and it was turning me on. I was just starting to bob up and down on it faster and faster when all of a sudden the driver's side door of Danny's car opened! I was fully exposed, up on all fours with just my bra and panties on and sucking Danny's big cock with a passion.
It was the bartender and he was unzipping his pants.
"I could use some of that," he said.
Danny put his hands on my hips and pushed me toward the open door.
"Suck it for him, sweetie. Show him how good you are."
The bartender took a step closer. With one hand on the steering wheel and the other on Danny's cock, I leaned in and opened wide. His cock wasn't nearly as long as Danny's but it was very thick and caused slurping noises as he moved his hips back and forth and basically fucked my mouth.
It was less than a minute when I felt him tense and he started to cum. I gagged a little, but stayed on it while Danny was cheering me on.
"That's a good girl. Take that nice warm load, baby. Yes, let him pump your mouth until he's all done."
I did just that, swallowing as much as I could.
Then, the bartender just zipped up, closed the door, got in his car and left.
Danny was edging and I knew he was about to explode. I never took my hand off his cock while I let him watch the bartender cum in my mouth. I re-positioned myself on the seat and decided to tease him a little. I slipped my bra straps down off my shoulders then reached down in the front of my panties and started jacking off for him.
"Okay, are you ready to take me home now?" I asked with a smile.
Without a word, he put his hands on my shoulders and pushed me down to his cock. I barely got my lips around the swollen head of it when he started to shoot. The first shot of his cum was so intense, it made me gag. I gulped as much of it as I could, then backed away and jacked him off with my mouth open letting him spray while I swallowed over and over. I started cumming while he was giving me his load and between us, we made somewhat of a mess on the front seat of his car but nobody was complaining!
I didn't bother putting my clothes on and sat next to him in just my bra and panties while he drove me home. When we pulled in my driveway, I rested my hand on his cock and asked if he'd like to come in. He was spent and declined, but he has my number and knows where I live.
There's another chapter in this story...
It was all I could do to keep from shouting out loud as I started to cum. I had never gushed in my panties before and it felt wonderful as he continued to rub me while I creamed in them.
I was out of breath as I looked over my shoulder. Trish still hadn't come out of the bathroom, the two guys were still playing pool and the bartender was stocking the cooler. Nobody had any idea that Danny had just made me fill my little red panties full of cum.
I was still trying to catch my breath as I thanked him and made my way to the men's room to clean up.
By the time I got out of the bathroom Danny and Trish were gone. I had a couple more beers and by then it was around midnight. The bartender said he was going to close early because it was so dead, so I drank up and left.
As I walked out to the parking lot I noticed another car parked right next to mine. It was Danny. I walked over and stood beside his open window.
"What happened to Trish?' I asked.
"I took her home. She was falling asleep," he said, a little disgusted. "I was hoping she would take care of this for me, but she was too drunk."
That's when I noticed his hard cock sticking up out of his unzipped jeans like a monument.
"I thought maybe you could help me out. Besides I never did get to see the pretty underwear you're wearing."
I walked around to the passenger side of his car, got in and slid across the seat next to him, wrapping my hand around his stiff cock.
"Danny, you are so nice and hard! You can't drive around with this big hard on. It would be dangerous," I said as I began working my hand up and down on his shaft. I stroked his big cock for a minute or so then took his hand and put it on his cock, letting him jack off while I eased back and started to undress for him.
I slowly unbuttoned my shirt and slipped it off my shoulders, letting him see my hard nipples sticking out of the lacy material of my little bra.
"Oh yeah, baby, That's what I want to see!" he said as he began stroking his cock faster.
I kicked my sandals off, undid the snaps of my jeans and wiggled out of them, letting him see me in just my bra and panties as I moved closer.
He slid one of my bra straps off my shoulder, leaned down and started sucking my hard nipple as his hand found its way to my lace covered cock.
"Oh honey, your panties are still wet. That was so sexy that you came for me in your panties standing right at the bar!"
"I loved it Danny. You're the only guy that's ever made me do that and I want to show my thanks for it." With that, I pulled him up off my chest, wrapped my hand around his big dick and started slowly jacking him off as I whispered in his ear, "If you promise not to tell Trish, I'd love to give you a blow job, Danny. You have such a beautiful cock. I really want to suck it for you."
"Yes, yes... I mean, no, I won't tell her, I promise! Just suck it for me sweetie, right now, please!"
I slid back a little on the seat, leaned down and held his big cock up straight with one hand and rested my other hand on his thigh. I flicked my tongue around the head, tasting his precum, then opened wide and went down on him. He stiffened and moaned in delight as I took him into my warm mouth.
"Oh honey, that feels so good! You are such a sexy little cock sucking girl!"
My little panties couldn't contain my hard cock and I reached down to stroke it while I was sucking him off. That was when he turned the dome light on in his car, flooding it like daylight. I got off his cock and looked up at him in question.
"You look so hot in your bra and panties with your mouth full of my cock. I want to look at your cute little ass while you suck me baby doll. Get up on your hands and knees and show it off for me."
I was a little leery of having the light on, but did as he said. Up on all fours, I was just getting into a nice rhythm of sucking his big cock again when I heard a noise. I came off his cock, jacking him off with one hand and resting my other on his shoulder.
"What was that?"
"Don't worry about it sweetheart, just keep sucking. I'm really close to giving you what you want." With that, he put his hand on the back of my head and pushed me back down to his waiting cock.
As I took him back in my mouth I could tell his shaft was getting thicker and the head of it was swelling. I knew I was going to make him cum soon and it was turning me on. I was just starting to bob up and down on it faster and faster when all of a sudden the driver's side door of Danny's car opened! I was fully exposed, up on all fours with just my bra and panties on and sucking Danny's big cock with a passion.
It was the bartender and he was unzipping his pants.
"I could use some of that," he said.
Danny put his hands on my hips and pushed me toward the open door.
"Suck it for him, sweetie. Show him how good you are."
The bartender took a step closer. With one hand on the steering wheel and the other on Danny's cock, I leaned in and opened wide. His cock wasn't nearly as long as Danny's but it was very thick and caused slurping noises as he moved his hips back and forth and basically fucked my mouth.
It was less than a minute when I felt him tense and he started to cum. I gagged a little, but stayed on it while Danny was cheering me on.
"That's a good girl. Take that nice warm load, baby. Yes, let him pump your mouth until he's all done."
I did just that, swallowing as much as I could.
Then, the bartender just zipped up, closed the door, got in his car and left.
Danny was edging and I knew he was about to explode. I never took my hand off his cock while I let him watch the bartender cum in my mouth. I re-positioned myself on the seat and decided to tease him a little. I slipped my bra straps down off my shoulders then reached down in the front of my panties and started jacking off for him.
"Okay, are you ready to take me home now?" I asked with a smile.
Without a word, he put his hands on my shoulders and pushed me down to his cock. I barely got my lips around the swollen head of it when he started to shoot. The first shot of his cum was so intense, it made me gag. I gulped as much of it as I could, then backed away and jacked him off with my mouth open letting him spray while I swallowed over and over. I started cumming while he was giving me his load and between us, we made somewhat of a mess on the front seat of his car but nobody was complaining!
I didn't bother putting my clothes on and sat next to him in just my bra and panties while he drove me home. When we pulled in my driveway, I rested my hand on his cock and asked if he'd like to come in. He was spent and declined, but he has my number and knows where I live.
There's another chapter in this story...