- Joined
- Aug 16, 2012
- Posts
- 1,068
- Media
- 233
- Likes
- 6,581
- Points
- 633
- Location
- Indianapolis, Indiana, US
- Sexuality
- 50% Straight, 50% Gay
- Gender
- Male
I stood by the rack of babydoll dresses. I don’t even know how I got to this point.
Lately I’ve been desiring trying to dress like a woman. I saw that Target was extremely slow and empty. So I decided to go try some on.
So… I grabbed 3 different styles. A long black dress, a floral summer dress, and a yellow babydoll and looked around I walked around the store holding them debating whether to go home and try them Or go try them on here. At some point in my walk I see a large man staring at me. He was tall and handsome. Built but also soft looking. His eyes and smile were very warm and sexy.
“Hi” I said shyly.
“Hi… how are you?” He replied confidently
“Fine. Fine” I said.
“I bet those dresses will look amazing on you” he smiled at me warmly.
“What? Oh oh. Uh these? These are for my wife dude” I stammered lying, trying to be macho. I’m not married I’m also single and haven’t been with a woman for a few years. I had been experimenting with my bisexual side since my divorce. I haven’t slept with a man but I’ve met up with a few for some playtime.
“I think they’re for you hun” he said to me smiling and he winked.
“Hahaha no no. For my wife
Bro” I laughed embarrassed and I’m sure red as an apple.
I attempted to walk away. But found myself in the condom section. “Ok hun. Have a great day” he said smiling and then turned his attention to the KY jelly shelf.
I walked away quickly and weaved through the clothes. I seemed to be alone again so I rushed into the mens fitting room. I undid my jeans and tossed them on the seat. I stood in front of the mirror in my royal blue silk panties I had purchased ln Amazon a few days ago... I looked ok… I guess. I’m chubby but not fat. I turned and looked at my fat ass in the blue panties. They were tight on my hips and round butt. I slipped the black dress on and opened the door. I appeared to be alone so I walked to the 360° mirror. I love how it seemed I had curves.
I went back and let the dress slip off fo the floor. I slipped the floral babydoll dress on. I went back out to the mirror. I looked at myself. I loved it. It made me look so sexy. I spun and I got a glimpse of my blue panties. Sexy.
I then got a glimpse of the corner. There stood the large man.
“Hey” he said warmly.
“So I was right?” He smiled.
“Uh….. uhm…. Yes” I dropped my eyes to look at the floor. Blushing.
“Don’t be shy… you look fabulous in that.” He said softly. Moving closer. “You look really nice. Very sexy”.
“Uh… oh… uh. Thank you “ I smiled.
“I’m Jason” he said.
“Hi Jason. I’m Matt”.
“Hi Matt” he winked
“Go try on the yellow one. I think that will be my favorite”
“What?… oh my god. Uhm no. It’s too embarrassing” i stuttered. Fuck I was so flustered. Was it hot in here.
“Please go try on the yellow, for me, Matt” he said smoothly “I want to see it on you”
“Uh. Ok… I guess” I went back to the fitting room. I turned to shut the door. I looked up at him. He was smiling at me. Jesus he’s cute I thought to myself as I shut the door.
“What the hell am I doing” I said to myself As I changed into the Yellow babydoll dress.
“You ok Matt?” He asked impatiently.
“Yeah. Sorry.. I’m coming” I said.
“Not yet you’re not” he said under his breath.
“What?” I asked “nothing hun” he replied.
I stepped out of the room and walked toward him. Not the mirror. Suddenly I wasn’t worried about my opinion of the dress. I needed his. What the hell was wrong with me.
I spun “well?”
“Stunning” he said staring at me. “You’re intoxicating”
“Thank you” I blushed hard.
His hand touched my hip. I shuttered.
“You are really sexy Matty” he smiled, his eyes were full of fire and lust
“Thank you” i smiled and turned to go change. I could feel him close behind.
I entered the changing room and saw in the mirror he had joined me. He closed the door behind b me. He slid the lock as I saw something in his hand. A box of condoms and KY jelly. I turned to face him
“Hiiii” I said sarcastically
“Look. I’m not usually like this” he said. “But something about you set me off”
“Uhm. Ok” I stared at him.
“What do you want?” I asked, already with a good idea of the answer.
“Are you gay Matt?” He asked.
“No. I’m bi… but I’ve never been with a man”
This seemed to intrigue him.
“Do you want to try?” He asked
“Yes” I said quickly without thinking about it
“With me maybe?” He asked his eyes wide
“Yes…. Maybe” I smiled at him. My hand reached out and touched his chest.
“Here?” He asked. Moving closer.
“Yes… maybe” I stepped back but winked at him
He pushed me against the mirror.
“Oh my ” I said involuntarily. He dropped the condoms and lube and His hands moved under the dress and massaged my ass. I purred and moaned against him. My head rested on his chest. My hands were flat against his stomach. I could feel his muscular abs. His hands lifted the dress ober my head and he tossed it to the floor. There is stood in my blue panties. The front bulging with my little Hard on. He removed his shirt. His chest and stomach were soft but you could definitely see defined muscles underneath a little extra meat. He unbuckled his belt and then his fly and let his jeans drop to the floor and stepped out of them. His boxers briefs strained trying to keep his manhood confined. Though I think his manhood was winning.
“You’re sexy” i whispered. My hand moved over his crotch. I rubbed his cock through his undies. He slipped his fingers under his waistband and slid his boxers off. His cock sprang to life in front of me.
“Jesus you’re huge” I groaned. His cock was 7” and thick. I rubbed the tip and then began to stroke him. Feeling it swell and harden.
He pulled me close grabbing my ass. He kissed me. “Mmmmm” I moaned against his kiss. His tongue wrestled with mine inside my mouth as my hand gripped his shaft. My cock ached inside my panties.
He moved the bench and pulled me to his side. He picked up the lube and poured it in his right hand. With his left hand he spun me to face the bench and bent me over. His lube covered right hand slid down my ass under my panties and I felt his finger exploding my butt. Then he found his target and his middle finger slipped inside me. He began to finger fuck my ass like a pussy.
“Aaaa aaaaa oh fuck. Oh god”
I groaned loudly. His hand slapping against my ass as he vigorously fingered me.
“Ssssssh” he whispered. Even though the slapping sound was louder than my moaning.
“Do you think you’re ready?” He asked softly…
“No.” I looked at him with fear in tm eyes.
“Ok…. Well… we will make it work….. eventually” he sat down and pulled me in front of him. He then wadded our jeans on each side of his legs and pulled me onto his lap. The jeans padding my legs from the hard surface of the bench
His hands rubbed my ass and squeezed my cheeks. “You have a nice fat ass” he moaned. “I can’t wait to get my cock inside it”.
“I’m scared Jason”. I admitted. Though his hands on my ass was making my dick throb. “You’re so big”
“I know. I’m sorry. But I want you. Badly. You want me right?” He asked and I felt him pull my panties to the side.
“Do you want me to wear a condom? He asked. Holding the box.
“No…. I’m ok like this” I said kissing him
He dropped the box to the floor ans added more lube to his hand. He reached behind me and stroked his cock. he began to slowly pressing his cock against my asscrack slipping it between my ass cheeks. He began to rock back and forth. Slowly lifting me until the timing worked and his cock slippery head lined up with my virgin hole. I could feel the heat coming off his throbbing cock.
“This is going to hurt for a while. You need to try to be quiet though” he said softly.
“Do you still want this? He asked sincerely. “I’ll stop if you want to stop”.
“Please… don’t stop” I moaned. I leaned against him and whispered again in his ear “Do not stop”
He gripped my asscheeks and spread them apart as he also pulled me down onto his cock. It wasn’t going in. Instead it felt as if he was shoving my asshole into my stomach.
He thrust a little more roughly but it only caused pain.
He leaned close to my face and nibbled my ear. “Relax baby” he whispered I took a deep breath clearing my mind and he thrust again.
“Jesus Christ” I screamed as my little ass was rammed open by his purple flared headed monster.
“Ssssssssssh baby” he whispered in my ear.
He thrust again, and I buried my fave against his shoulder and screamed again” “aaaaaaaaaaa you’re ripping me apart jason!!!”
He stopped.
“Do not stop” I moaned against him.
“I’m sorry baby” he whispered and pulled me down and lifted his hips and thrust hard into me
“Fuuucucccckkk. Uuuuuggggnnnn Jason. Jesus. Oh my god. Aaaaaaaaaaaa!!! I screamed against his shoulder again. But knew the worst was over. His entire cock was buried inside me. It felt like his throbbing head was in my stomach and I swear I could feel his l blood pumping into his shaft as my walls stretched around him and gripped him like a Vice.
He looked at me. “You’re so tight baby… you feel incredible”
“You feel good too” I smiled but winced at the same time. It hurt each time his pumped blood and made his head flare deep inside me.
“Let’s let you adjust” he held me still and kissed me. “Just relax”
My ass kept clenching around his invading manhood. It hurt but it also felt amazing.
“I’m ready to continue” I whispered and lifted myself up sliding partially up his massive tool. “Oh my god” escaped my lips feeling his massive cock slide along my stretched walls
“Oh fuck” I groaned loudly as He pulled me back down on it.
He gripped my fat ass with his big hands and began to work his meat in and out of me.
“Ugh ugh ugh ugh ugh ugh Ugh ugh ugh ugh “ i grunted as he pummeled my squishy ass.
“You look so sexy riding my cock” he moaned in my ear.
My balls ached and I felt myself about cum
“I’m going to cum Jason” I moaned in his ear.
“Cum baby. Cum on my cock” he pulled my panties down under my balls as my cock jerked and my cum splashed on his stomach and chest. “I’m cumming. I’m Cumming Jason!” I yelled.
He gripped my ass harder and began to slam me down on his cock
“Oh yeah baby” he groaned “I’m going to cum. I’m going to fill you with my seed!” He slapped my left asscheek. Then my right.
“Oh fuck Jason” I moaned softly as I laid against him, my cum making our bodies slide against each other as he fucked me as hard as he could.
“Ooohh. Ffuuucccckkkk uuuuunnngggg nnnngggnngngg. Oh Unngg” He gripped at me ass and pulled me down hard and held me as I get his cock explode deep inside me. My walls gripping him tightly I could feel his cock swell with each spray of cum. I felt it running down his shaft and leaking out of my stretched asshole down my balls to the bench.
After he stopped emptying his balls inside me he held me tightly and thrust into me a few times. Then he leaned back against the wall and held me. We sat like this for a while and then he said he needed to leave. He stood, helped me into my new dress again, and dressed and began to walk out “you need to buy the dresses. You look sexy as fuck”, and he walked out. My ass stretched open, dripping his seed under the dress. I looked at myself in the mirror. I was bright red and sweaty. My cheeks were flushed. I turned and looked at my ass, lifting the dress. His large handprints were emblazoned on my ass cheeks. Fuck I looked sexy. He was right.
Sent from my iPhone
Lately I’ve been desiring trying to dress like a woman. I saw that Target was extremely slow and empty. So I decided to go try some on.
So… I grabbed 3 different styles. A long black dress, a floral summer dress, and a yellow babydoll and looked around I walked around the store holding them debating whether to go home and try them Or go try them on here. At some point in my walk I see a large man staring at me. He was tall and handsome. Built but also soft looking. His eyes and smile were very warm and sexy.
“Hi” I said shyly.
“Hi… how are you?” He replied confidently
“Fine. Fine” I said.
“I bet those dresses will look amazing on you” he smiled at me warmly.
“What? Oh oh. Uh these? These are for my wife dude” I stammered lying, trying to be macho. I’m not married I’m also single and haven’t been with a woman for a few years. I had been experimenting with my bisexual side since my divorce. I haven’t slept with a man but I’ve met up with a few for some playtime.
“I think they’re for you hun” he said to me smiling and he winked.
“Hahaha no no. For my wife
Bro” I laughed embarrassed and I’m sure red as an apple.
I attempted to walk away. But found myself in the condom section. “Ok hun. Have a great day” he said smiling and then turned his attention to the KY jelly shelf.
I walked away quickly and weaved through the clothes. I seemed to be alone again so I rushed into the mens fitting room. I undid my jeans and tossed them on the seat. I stood in front of the mirror in my royal blue silk panties I had purchased ln Amazon a few days ago... I looked ok… I guess. I’m chubby but not fat. I turned and looked at my fat ass in the blue panties. They were tight on my hips and round butt. I slipped the black dress on and opened the door. I appeared to be alone so I walked to the 360° mirror. I love how it seemed I had curves.
I went back and let the dress slip off fo the floor. I slipped the floral babydoll dress on. I went back out to the mirror. I looked at myself. I loved it. It made me look so sexy. I spun and I got a glimpse of my blue panties. Sexy.
I then got a glimpse of the corner. There stood the large man.
“Hey” he said warmly.
“So I was right?” He smiled.
“Uh….. uhm…. Yes” I dropped my eyes to look at the floor. Blushing.
“Don’t be shy… you look fabulous in that.” He said softly. Moving closer. “You look really nice. Very sexy”.
“Uh… oh… uh. Thank you “ I smiled.
“I’m Jason” he said.
“Hi Jason. I’m Matt”.
“Hi Matt” he winked
“Go try on the yellow one. I think that will be my favorite”
“What?… oh my god. Uhm no. It’s too embarrassing” i stuttered. Fuck I was so flustered. Was it hot in here.
“Please go try on the yellow, for me, Matt” he said smoothly “I want to see it on you”
“Uh. Ok… I guess” I went back to the fitting room. I turned to shut the door. I looked up at him. He was smiling at me. Jesus he’s cute I thought to myself as I shut the door.
“What the hell am I doing” I said to myself As I changed into the Yellow babydoll dress.
“You ok Matt?” He asked impatiently.
“Yeah. Sorry.. I’m coming” I said.
“Not yet you’re not” he said under his breath.
“What?” I asked “nothing hun” he replied.
I stepped out of the room and walked toward him. Not the mirror. Suddenly I wasn’t worried about my opinion of the dress. I needed his. What the hell was wrong with me.
I spun “well?”
“Stunning” he said staring at me. “You’re intoxicating”
“Thank you” I blushed hard.
His hand touched my hip. I shuttered.
“You are really sexy Matty” he smiled, his eyes were full of fire and lust
“Thank you” i smiled and turned to go change. I could feel him close behind.
I entered the changing room and saw in the mirror he had joined me. He closed the door behind b me. He slid the lock as I saw something in his hand. A box of condoms and KY jelly. I turned to face him
“Hiiii” I said sarcastically
“Look. I’m not usually like this” he said. “But something about you set me off”
“Uhm. Ok” I stared at him.
“What do you want?” I asked, already with a good idea of the answer.
“Are you gay Matt?” He asked.
“No. I’m bi… but I’ve never been with a man”
This seemed to intrigue him.
“Do you want to try?” He asked
“Yes” I said quickly without thinking about it
“With me maybe?” He asked his eyes wide
“Yes…. Maybe” I smiled at him. My hand reached out and touched his chest.
“Here?” He asked. Moving closer.
“Yes… maybe” I stepped back but winked at him
He pushed me against the mirror.
“Oh my ” I said involuntarily. He dropped the condoms and lube and His hands moved under the dress and massaged my ass. I purred and moaned against him. My head rested on his chest. My hands were flat against his stomach. I could feel his muscular abs. His hands lifted the dress ober my head and he tossed it to the floor. There is stood in my blue panties. The front bulging with my little Hard on. He removed his shirt. His chest and stomach were soft but you could definitely see defined muscles underneath a little extra meat. He unbuckled his belt and then his fly and let his jeans drop to the floor and stepped out of them. His boxers briefs strained trying to keep his manhood confined. Though I think his manhood was winning.
“You’re sexy” i whispered. My hand moved over his crotch. I rubbed his cock through his undies. He slipped his fingers under his waistband and slid his boxers off. His cock sprang to life in front of me.
“Jesus you’re huge” I groaned. His cock was 7” and thick. I rubbed the tip and then began to stroke him. Feeling it swell and harden.
He pulled me close grabbing my ass. He kissed me. “Mmmmm” I moaned against his kiss. His tongue wrestled with mine inside my mouth as my hand gripped his shaft. My cock ached inside my panties.
He moved the bench and pulled me to his side. He picked up the lube and poured it in his right hand. With his left hand he spun me to face the bench and bent me over. His lube covered right hand slid down my ass under my panties and I felt his finger exploding my butt. Then he found his target and his middle finger slipped inside me. He began to finger fuck my ass like a pussy.
“Aaaa aaaaa oh fuck. Oh god”
I groaned loudly. His hand slapping against my ass as he vigorously fingered me.
“Ssssssh” he whispered. Even though the slapping sound was louder than my moaning.
“Do you think you’re ready?” He asked softly…
“No.” I looked at him with fear in tm eyes.
“Ok…. Well… we will make it work….. eventually” he sat down and pulled me in front of him. He then wadded our jeans on each side of his legs and pulled me onto his lap. The jeans padding my legs from the hard surface of the bench
His hands rubbed my ass and squeezed my cheeks. “You have a nice fat ass” he moaned. “I can’t wait to get my cock inside it”.
“I’m scared Jason”. I admitted. Though his hands on my ass was making my dick throb. “You’re so big”
“I know. I’m sorry. But I want you. Badly. You want me right?” He asked and I felt him pull my panties to the side.
“Do you want me to wear a condom? He asked. Holding the box.
“No…. I’m ok like this” I said kissing him
He dropped the box to the floor ans added more lube to his hand. He reached behind me and stroked his cock. he began to slowly pressing his cock against my asscrack slipping it between my ass cheeks. He began to rock back and forth. Slowly lifting me until the timing worked and his cock slippery head lined up with my virgin hole. I could feel the heat coming off his throbbing cock.
“This is going to hurt for a while. You need to try to be quiet though” he said softly.
“Do you still want this? He asked sincerely. “I’ll stop if you want to stop”.
“Please… don’t stop” I moaned. I leaned against him and whispered again in his ear “Do not stop”
He gripped my asscheeks and spread them apart as he also pulled me down onto his cock. It wasn’t going in. Instead it felt as if he was shoving my asshole into my stomach.
He thrust a little more roughly but it only caused pain.
He leaned close to my face and nibbled my ear. “Relax baby” he whispered I took a deep breath clearing my mind and he thrust again.
“Jesus Christ” I screamed as my little ass was rammed open by his purple flared headed monster.
“Ssssssssssh baby” he whispered in my ear.
He thrust again, and I buried my fave against his shoulder and screamed again” “aaaaaaaaaaa you’re ripping me apart jason!!!”
He stopped.
“Do not stop” I moaned against him.
“I’m sorry baby” he whispered and pulled me down and lifted his hips and thrust hard into me
“Fuuucucccckkk. Uuuuuggggnnnn Jason. Jesus. Oh my god. Aaaaaaaaaaaa!!! I screamed against his shoulder again. But knew the worst was over. His entire cock was buried inside me. It felt like his throbbing head was in my stomach and I swear I could feel his l blood pumping into his shaft as my walls stretched around him and gripped him like a Vice.
He looked at me. “You’re so tight baby… you feel incredible”
“You feel good too” I smiled but winced at the same time. It hurt each time his pumped blood and made his head flare deep inside me.
“Let’s let you adjust” he held me still and kissed me. “Just relax”
My ass kept clenching around his invading manhood. It hurt but it also felt amazing.
“I’m ready to continue” I whispered and lifted myself up sliding partially up his massive tool. “Oh my god” escaped my lips feeling his massive cock slide along my stretched walls
“Oh fuck” I groaned loudly as He pulled me back down on it.
He gripped my fat ass with his big hands and began to work his meat in and out of me.
“Ugh ugh ugh ugh ugh ugh Ugh ugh ugh ugh “ i grunted as he pummeled my squishy ass.
“You look so sexy riding my cock” he moaned in my ear.
My balls ached and I felt myself about cum
“I’m going to cum Jason” I moaned in his ear.
“Cum baby. Cum on my cock” he pulled my panties down under my balls as my cock jerked and my cum splashed on his stomach and chest. “I’m cumming. I’m Cumming Jason!” I yelled.
He gripped my ass harder and began to slam me down on his cock
“Oh yeah baby” he groaned “I’m going to cum. I’m going to fill you with my seed!” He slapped my left asscheek. Then my right.
“Oh fuck Jason” I moaned softly as I laid against him, my cum making our bodies slide against each other as he fucked me as hard as he could.
“Ooohh. Ffuuucccckkkk uuuuunnngggg nnnngggnngngg. Oh Unngg” He gripped at me ass and pulled me down hard and held me as I get his cock explode deep inside me. My walls gripping him tightly I could feel his cock swell with each spray of cum. I felt it running down his shaft and leaking out of my stretched asshole down my balls to the bench.
After he stopped emptying his balls inside me he held me tightly and thrust into me a few times. Then he leaned back against the wall and held me. We sat like this for a while and then he said he needed to leave. He stood, helped me into my new dress again, and dressed and began to walk out “you need to buy the dresses. You look sexy as fuck”, and he walked out. My ass stretched open, dripping his seed under the dress. I looked at myself in the mirror. I was bright red and sweaty. My cheeks were flushed. I turned and looked at my ass, lifting the dress. His large handprints were emblazoned on my ass cheeks. Fuck I looked sexy. He was right.
Sent from my iPhone
