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Playing together in underwear

Posted by: Age: 50 Posted on: 6 comments
13 likes 287 views Category: Sex Stories Fetish Tags: Underwear, tighty whities, mutual masturbation, frotting, fetish, gay

Hot hotel encounter with another guy, exploring our mutual underwear fetish, with erotic underwear play, frotting, oral, and mutual masturbation 


This is a true story from some years ago. I have had an underwear fetish since I was a boy, and I love to masturbate in my underpants, rubbing my penis through the soft cotton and watching myself in a mirror, posing, looking at my bulging pouch, and slowly pulling the waistband down in the front and then in the back to reveal my erect penis and my bare bottom. I get aroused just looking at men's underwear, and even more turned on seeing other guys in their underwear. I  especially like traditional tighty whities. I have stolen other guys briefs several times, and like to parade around my bedroom and pose in front of my mirror wearing them. I fantasized a lot about playing with another guy in briefs but I had not yet done so.

I was away on a business trip, staying in a hotel for a week and I decided to try to find someone who shared my underwear fetish, and set up an encounter in my hotel room. I put an ad in Craigslist, with a picture of me in my underwear, and got several responses. The best was from a guy called Dave, who lived locally. He sent me a picture of him in his white briefs, he was about my age, and looked really hot in a pair of Fruit of The Looms. We arranged for him to come up to my hotel room the next evening.

I was nervous before he arrived. I showered and put on a pair of my favorite white Jockey briefs, then dressed casually in jeans and a T-shirt. I spread half a dozen different pairs of my underpants over the desk and put a rotating slide show of hot guys in white briefs on my laptop. Then I paced the room, waiting for him to arrive. I had a semi erection in anticipation, but I had butterflies in my stomach too.

Dave was late. He sent me a last minute message saying that he was held up at work, and was it OK if he came straight from there? He would have no time to go home and change first. Of course I said OK.  When he finally arrived I was surprised and delighted to find that he was wearing a UPS driver's uniform! He looked so hot in his dark brown uniform with a big leather belt and big work boots. He removed his boots and went straight over to examine my underwear collection on the desk.  It was hot watching him handle my underpants, examining them carefully. He had a bulge in the front of his brown uniform pants already, My penis was getting hard too. He rubbed some of my underpants on his face, and told me which ones he liked best. Next we watched my slide show together, commenting on the pictures we liked most. He reached out and fondled me through the front of my jeans while we watched the slide show and I groped him through his uniform, feeling his boner in his pants. He wrapped his arms around me and kissed me. I could feel his hard dick rub against mine through his uniform. Our hands were all over each other, touching, feeling and fondling each other through our clothes. Slowly I unbuttoned his brown uniform shirt and pulled it off and he removed my t-shirt. I kissed and licked and sucked his nipples and we rubbed our bare chests together. He reached down and unzipped my fly and slipped his fingers inside, caressing my erect penis lightly through my underpants.

His tongue slipped into my mouth and I felt his fingers explore the waistband of my jeans. He slipped his fingertips under the waistband and played with the top of my briefs. I ran my hand down to the bulging package in his crotch and I caressed his swollen manhood through the thick cotton of his work pants. I fondled and caressed him through his pants as we kissed passionately. I felt his fingers probe a little deeper inside my pants, sliding between my jeans and my underpants, exploring in that tight space as our tongues pushed deep into each others mouth. 

After a few minutes he stepped back and said, "I can't wait any longer to see your underwear!" He undid the waistband of my jeans. It was very arousing having him undress me, and slowly expose my underpants to his view. He slid my jeans right down and I kicked them off. I stood before him, stripped to my bulging tighty whities. He stared at the tent in my undies and moaned softly. Then he reached out and ran his fingers over the pouch in my briefs, tracing the outline of my rock-hard penis through the cotton, feeling the head of my knob, running his fingertips up and down my shaft and then gently cradling and squeezing my balls. I felt a little pre-cum ooze from my dick, and a small, sticky damp spot appeared on the front of my bulging briefs.

I slipped my hand down inside the waistband of his pants as he caressed me, and we kissed again. I pushed my hand deep inside his pants and fondled him through his underpants. I could feel that his erection was as strong as mine was, and his penis felt long and hard through the cotton. He stopped kissing me and stepped back again. Smiling, he took my hand in his and led me over to the bed. He lay on his back on the bed in his brown work pants and pulled me towards him. "Climb on top of me," he suggested. "I want to feel your body laying on me and rubbing against me."

I climbed onto the bed and lay full length on top of him in my underpants, my bare right thigh between his thighs, my bare skin against the coarse cotton of his uniform pants, my crotch against his crotch. I kissed him hard and he reached round and grabbed my bottom, pulling me tight against him. Our penises rubbed together through his pants and my underpants. I moved my hips up and down, rubbing my crotch against his, then I started to rock slowly and rhythmically on top of him, pushing against him, humping him through his uniform, He slipped his hand inside the back of my underpants and ran his hand over my bare bottom, exploring the cheeks of my bottom inside my underpants. We were both moaning and groaning as we rocked together harder and faster, grinding our crotches together. Finally I sat up, panting. "I don't want to cum yet buddy," I said. "I want to see you in your underpants first!" He grinned as I rolled off him.

He stood up and I knelt in front of him, I undid his belt, unzipped his fly and slid his pants down, revealing his bulging white FTL briefs. I gazed at his underwear for a few minutes. "you look so hot in your underpants" I muttered hoarsly.  I reached out and gently squeezed his penis through his briefs, feeling his swollen shaft through the material, manipulating and stroking him. Then he reached down and pulled me to my feet. We stood in front of a big mirror on the wall with the bulging pouches of our underpants nestled together, our hands all over each other. We watched ourselves in the mirror as we rubbed our erect penises together through our underpants and rubbed and stroked and fondled each other. He put his hand down the back of my underpants and fondled my bare bottom again and I did the same to him. We spent some time standing together like that in our underpants in front of the mirror, kissing and fondling each other, we were both leaking a lot of pre-cum by now.

He led me back over to the bed and told me to sit down, then told me to lie back on the bed with my feet on the floor. I did as he asked and he knelt on the floor between my legs. He leant forward and very gently brushed his lips over the bulging outline of my throbbing dick. He kissed my dick-head through the cotton, and then ran his tongue along the length of my shaft. Next he licked my balls through the cotton. I was moaning and squirming in ecstasy. Finally he sucked my balls right into his mouth, sucking them together through the pouch of my briefs, then sucking them individually, pulling them deep into his hot mouth and rolling them around with his tongue. It felt absolutely fantastic. I was moaning and panting and groaning louder and louder. Suddenly he stopped and sat up and said, "I know you don't want to cum yet so I'd better give you a break."  

He sat on the bed next to me and I sat up and kissed his chest. I pushed my thigh between his thigh and grabbed his ass. I ran my tongue over his chest and kissed and licked his nipples as I fondled his ass and he rubbed his crotch against mine. Then he gently but firmly pushed me back down on the bed. He wrapped his arms around me and we lay with our bodies tangled together, kissing. I loved the feeling of our bare skin rubbing together, and the feel of our underpants pressed against each other. Our hands quickly drifted to each others penis. We groped and rubbed each other. I took his erect penis firmly in my hand and stroked it through the cotton. I said, "Dave, I love the feel of your big dick through your briefs." He murmured, "Fuck yeah Alex, masturbate me in my underpants, that feels so good" He rubbed my throbbing penis firmly with his hand.  We lay together on the hotel bed, masturbating each other in our tighty whities.

After a while Dave stopped masturbating me and put his hand on my chest. Very slowly he moved his hand down my chest, down over my belly, down inside my underpants. He reached right down into my underpants and fondled my penis and my balls inside there. He rubbed his thumb over my piss slit and around the head of my knob, then down my shaft to my balls. He played with my nutsack and squeezed my balls deep inside my briefs as I groped him through his. "Fuck man, your penis feels so good," he muttered. "I love groping you inside your underpants and playing with your balls". 

He climbed over the top of me and knelt straddling me, I felt like he was in command now, doing whatever he wanted to me. My tumescent cock was standing straight up, making a big tent in my white briefs. He shuffled forward on his knees, bringing his crotch up to my face. I opened my mouth and he pressed his balls against my face. Hungrily I sucked his balls through his briefs; first both of them together, then individually, just as he had sucked mine. He groaned as I sucked hard on each of his testicles, and he ground his crotch against my face. I just gazed up at him and sucked his big balls. He eventually rolled off me and sat on the bed. I immediately bent over his lap and kissed and licked his hard cock through his underpants. I licked and nibbled on the tip of his big knob through his bulging briefs, then ran my tongue down his long shaft. He put his hand on my head and ran his fingers through my hair as I sucked him off through his underpants, sucking his big cock deep into my hot mouth through the wet cotton. My head bobbed up and down in his lap as I moved my mouth up and down the whole length of his shaft, sucking hard and flicking the head of his dick with my tongue.  Finally he yelled "Stop! Stop Alex or I'm gonna cum! I don't want to cum yet. Wow, you are a great fucking cocksucker!" I took his dick out of my mouth and grinned at him. "Ok buddy, I'll let your cock calm down a bit!"

I decided to take charge for a while. I rolled him over on to his stomach, and played with his cute little bottom for a while, caressing his cheeks through his underpants and reaching inside to play with his bare bottom. I spanked his bottom lightly a few times, slapping it through his underpants, and also pulled the back of his underpants down just under his cheeks to fully expose his cute bottom and give him some bare bottom spanking. Then I rubbed and massaged his bottom for a while.  When I thought he had calmed down enough I pulled the back of his briefs back up and told him to roll back over onto his back.  I pushed his legs way back so that his ankles were either side of his head and his bottom was in the air. I positioned my knees either side of his bottom and leant forward, with my hands on the pillows. I lowered my crotch down against his waiting bottom and pushed my boner against his crack. Slowly I started to thrust my hips, fucking his crack through our underpants. I ground against him, gradually increasing the intensity and pace, pushing my penis deeper and deeper between the cotton covered cheeks of his bottom. Still not time to cum yet! I stopped and pulled away from him, my body heaving and my cock throbbing.

He took the lead again now. He asked me to kneel in front of him. Then pulled the waistband of my underpants outwards and gently lowered it over the head of my erect penis, fully exposing my erection to his view for the first time. Then he pulled the front of my briefs down to the base of my penis, and tucked the waistband under my balls.  He pushed me down on the bed and lay on top of me, my bare dick trapped between our bodies. He gently rocked his hips, rubbing my cock between us.

I hooked my thumbs around the waistband of his briefs and pulled them down at the front. He sat up a little and I pulled his waistband down under his balls, like he had done to mine. I stared at his big erection, poking straight out at me.  He slapped it down against my belly and kissed me on the lips again. He lay on top of me, our underwear pulled tight under our balls, our bare penises rubbing together between our bellies. He pushed against me and I arched my back and pushed back against him. We rubbed our bodies together in a sweaty tangle, grinding our erections together. Our pre-cum oozed between us and mingled together, lubricating our cocks as they slid against each other. Our balls slapped together too, held tightly in place by the stretched elastic of our waistbands. We were like animals now, humping together wildly, sweating and groaning and grunting, tongues pushed deeply down each others throat, arms wrapped tight around each other.

He stopped humping and knelt up between my legs and pulled the waistband of my briefs out from under my balls. Then he released his own balls from the tight waistband of his own briefs and lay on top of me. We humped together again face to face, grinding our bulges together and kissing.  He pulled his cock out of the fly of his underpants and stuck it inside the fly of my underpants, so that our two cocks were nestled together inside one pair of underpants as we humped together, harder and faster. I wrapped my arms around him and kissed him hard as he ground his cock hard against mine, his body sliding against mine, my hands on his bottom, pulling him tighter against me. I wrapped my legs around his. We humped together faster and faster, harder and harder, both grunting and moaning loudly, panting and sweating, cock fucking each other wildly in our underpants, our cocks grinding together hard as we thrust our hips together, pumping against each other, bucking and rolling around on the bed, our bodies locked together, frotting each other wildly as we both got closer and closer to climax, moaning, "Ohhhh ooooohhh fuckkk, ohhhh, ohhhhh fuckkkk man!" Suddenly I felt his whole body go rigid, his back arched, he let out a strangled cry and I felt squirt after squirt of his hot jizz gushing inside my underpants, all over my cock, which immediately made me cum too, with the most incredibly intense orgasm. My ass muscles clenched and I shot a huge load of cum into my underpants as waves of pleasure washed over me. Our hot cum mixed and spread between our bellies and crotches and underwear as we continued grinding together and kissing. Afterwards we lay in each others arms for a while, kissing and cuddling, in our sticky, cum filled underpants.

When it was time for him to get dressed and leave we decided to keep each others cum filled underpants as souvenirs. I wore his under my business clothes the next day at my work meetings, and had an erection all day thinking about him and remembering what we had done together.

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