Craigslist ad got me the hard ass pounding I was c
- 1 year ago
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Craigslist Crossdresser free porn video
It finally happened. I got a response! I’d been corresponding with him on Craigslist, but then suddenly Craigslist personals were banned. I tried to reply to the Craigslist generated email that I thought was his, but I’d deleted all of his email’s in a moment of weakness. Now I had no way to get in touch with him. He’d posted about hosting crossdressers and providing a safe, relaxed place for us to fulfill our fantasies. He said he would be gentle. I’d told him who I was, that I liked to wear women’s clothing. I told him how I’d dressed for my wife, until she lost interest in me. I’d told him about the skirts, the panties, the lipstick and the bras. I told him how I’d never shaved my legs but I wanted to. I wanted someone to fuck me so good that I just had to shave them. We’d agreed to meet at a bar in regular men’s clothes but that I’d definitely be wearing women’s underwear underneath mine. And then I’d deleted everything, and had no way to reach out. But finally he did. I must have used one of my own email address for at least one reply and he found me. He still wanted to meet and he still wanted me in panties. He knew I wasn’t passable and he would have to take his time turning me out.
I slipped out of my house on the anointed evening, wearing red satin panties hidden under my boxers. I’d done some ‘manscaping’ so that I wasn’t too hairy and shaved my beard close. I stashed some other items in my car for later - high heeled shoes, fishnets, and tight, tight pants. The bar wasn’t some creepy dive, it was a nice neighborhood bar, and many of the other folks there knew him. Some of them probably even knew he was gay and he was going to take me home and fuck me in the ass like a little sissy, but it didn’t matter. Everyone was super cool and we had a couple of drinks and we laughed. He even started to make moves on me like a girl. He snuck a hand on my knee and rubbed my thigh, when no one was looking. He rubbed my shoulders with his hands a couple of times when he got up to use the bathroom. Somehow I thought this was going to feel like a job interview, but it didn’t. He listened to what I had to say and gave me his attention. He listened for feminity, not for the content of my sentences. I felt so frisky and special. I wanted to scream, “I’m about to be a faggot” at the top of my lungs. My heart raced, and my skin went cold with anticipation. He walked me to my car around the corner and told me to follow him, back to his house, where we could be alone and try all the things I’d been wanting to try. He walked a few steps, turned back and embraced me, out of view of the club. He put his hands on my waist and leaned in for a kiss. I obliged. I closed my eyes and felt his scratchy stubble and his searching lips, until they met mine. He leaned in and pinched my ass just a little bit harder. He kissed me more, all over my face and rubbed my back up and down. I could feel his hard erection pressed up against mine. He traced the elastic waistband of my boxers and then slid a finger in to make sure I was wearing something sexier underneath. With that, he walked to his car, and I followed him through the back streets to his little suburban home.
He waited for me in his driveway, opened the door of my car for me and helped me out, took my hand and escorted me inside. I grabbed a big purse I’d brought with a few sexy items in it. When we were safely inside, I closed the door behind me and just stood there. He didn’t say a word, but simple walked up to me, kissed me and unzipped my fly. With both hands cradling my head, he kissed me. Then he worked a hand down and pushed my jeans down and then my boxers. I stepped out of them and stood there awkwardly in my red lace panties. I was finally showing off my pantied ass for a big strong man and I’d loved it. So did he. He ran his finger tips along the seams and across the silky backside. He gave my ass a couple of squeezes and a gentle pat, then he sat down on the couch and just gazed at me. So I put on the heels I’d brought and walked back and forth for him, as ladylike as I could. I added lipstick and blew him a few kisses. I hooked a bras in the front and turned in around and slipped my arms into the loops. That was a enough. One day, I wanted to do my makeup and really get fixed up, but not tonight. There wasn’t time. The feeling was too intense and the urges too strong for all of that. I’d been denying these fantasies for too many years and I was tired of it and I wasn’t afraid anymore. I wanted to be the center of attention and a thing of beauty. I wanted a lover who could take the lead and tell me what to do. I wanted to be fondled and fucked by a big strong man. I wanted him to have his way with me. I was going through with it tonight and I was gonna take it up the ass.
I bent forward and kissed him on the cheek and sat between his legs on the floor. He rubbed my shoulders and my hair. I bit at the seams of his denim jeans with my teeth and then opened up, flared my nostrils and took in the aroma of manhood. I lingered there and then slowly slipped down his the jeans. I could see his big print through his white briefs and I pressed my lips against it. When I leaned back and felt his hard tent pitching against my neck. I closed my eyes and felt the warmth and the pulsing against my ear. The smell of his dick was all around me. I closed my eyes and just rubbed my face all of over the cotton cloth and the hard tool below.
I knew that the next step was to turn and chug some cock, but I was getting scared again and I needed a few minutes to collect myself. Just what exactly had I gotten myself into? This was no lady boy. This was a real man, who could really overpower me if he got too excited. He could wrestle me to the ground, pin me down and drive his phallus right through me. Once he got moving, he was not going to want to stop. He’d cover me in lube and just go to town. I’d be laying on my stomach with an arched back and he’d be rubbing and pinching my tits with his hands. I’d be whining and squealing and squirming and getting all sweaty.
My heart would be racing and I’d be panting and short of breath and there’d be no escaping. Just then, I heard a fim voice that snapped me out of my reverie. “Time to put it in your mouth sissy.” and then as if to reassure me, “You can do it you little fag. You’re ready for a dick aren’t you?.” I was embarrassed and ashamed and some part of me wanted to stand up and walk out and go back to my masculine life, but I also longed for tight jeans, and femmy blouses, and skimpy lacy lingerie. I could cook and clean and do laundry and suck dick every day in a little apron. I turned and leaned my head against his inner thigh and looked up at him submissively and he ran his fingers through my hair again. Then out of nowhere he took his semi-hard cock and bopped me in the nose with it. I smiled and started to chase it around with my tongue. At that moment I realized that I was falling right into my new role and I was pleased with myself.
I kiss his balls and his thighs and the base of his shaft. I stroke him and lick my way up the shaft. Finally I close my eyes take his cock deep in my mouth and explore it’s head with my tongue. He likes that and he smiles and I keep going. He chokes me a little and I keep going and he does it again. The third time, he grabs the back of my neck and forces his cock down my throat. I’m overpowered and tearing up. I feel so feminine this way. I look up and he slaps me across the face. He holds me by the chin, peering down into my eyes and slaps me harder. I start to shake and cry. I’m sobbing now and tears are rolling down my cheeks. He shoves the cock back in my mouth and I suck with everything I’ve got. I’m tingling all over and my tongue goes back and forth against the underside of his penis. Now he lifts me onto couch and I’m sideways on it, almost fetal. I’m nursing away on his meat and he spanks me on my red-pantied bottom. He slips his hand inside the panties and starts exploring. He licks his finger and makes circles around my asshole with it. That feels great! He pulls me up and puts me right over his knee and really spanks me good. “You lit-tle faggot he are doing such a good job” I get scared and filled with adrenaline. I am gonna take it so hard up the ass that I’ll walk funny. He spanks some more and I cry like a girl and the sound of my gay little cries makes me even harder. I am so glad I’m going through with this. I guess I was just a little bitch all along. I tighten up with each spank and then go limp over his knees. He cups my butt and finger tips find their way to my anus, bumping rhythmically against it though the satin. I’m sniffling back the tears. He hauls back his palm and spanks again and my flight impulse kicks in. I skamper down onto the floor head first and lay there crumpled up panting for air.
He stands up and lording over me, stepping out of his jeans and flinging his shirt across the room. He kneels and gets down on all fours and crawls towards me. I spring forward and he pounces and suddenly that big dick is against my ass. I enveloped in a warm blanket of manhood, hairy chest against my back. One of his hands is on my stomach and the other is on the small of my back. There is more grinding now and more kisses, this time on the ears. I purr and coo softly and grind back to meet him. Everything is going even better than planned and I’m definitely gonna be getting penetrated soon. There’ll be condoms and lube to find and it’ll take a lot the first time. It’ll take a while to loosen me up to where I need to be. That’s something I’m looking forward to. I want to be a good fuck someday and not just in a virginal sort of way, so work that thing loose big boy! As for tonight, I’ll cry and whimper and sob so much. It’ll hurt, but I’ll love it. He’ll thrust in and out and in again. “Ahh” that thrust was deep. “Ah Aaahh” That one was even deeper. A high pitched squeal will mean pull it out and add some lube. How can I ever wear anything but panties after this. I willingly set up a date with another man and now he’s turning my out something fierce. I’m imagining the way I’ll walk when he’s done pounding me and I’m seeded. It’ll be more of a sashay from now on. He’s getting sweatier and breathing harder now and I just slosh back and forth on rug like a rag mop. He stabs with purpose now, and grunts with each thrust. Finally he holds it in there real deep and shoots his load, filling the head of the condom, somewhere way up in my canal. When he pulls out and turns over, I embrace him. I kiss his face and neck and run my fingers all over his back. He rocks his hips against me and and grinds out his last drops. He reaches a finger down and inserts it in my anus and I grip it tight and cum all over my belly. He relaxes himself and just lays on me, and I feel the fresh cum mixing with his belly and chest hair as he looks into my eyes. Then he collapses and I feel his hot breath against my neck as he winds down. Finally, he lays next to me and I can’t help but clean up all that salty cum on him with my tongue. I better put those panties back on while he’s asleep and get dolled up as best I can. It’s going to be a long night.
I slipped out of my house on the anointed evening, wearing red satin panties hidden under my boxers. I’d done some ‘manscaping’ so that I wasn’t too hairy and shaved my beard close. I stashed some other items in my car for later - high heeled shoes, fishnets, and tight, tight pants. The bar wasn’t some creepy dive, it was a nice neighborhood bar, and many of the other folks there knew him. Some of them probably even knew he was gay and he was going to take me home and fuck me in the ass like a little sissy, but it didn’t matter. Everyone was super cool and we had a couple of drinks and we laughed. He even started to make moves on me like a girl. He snuck a hand on my knee and rubbed my thigh, when no one was looking. He rubbed my shoulders with his hands a couple of times when he got up to use the bathroom. Somehow I thought this was going to feel like a job interview, but it didn’t. He listened to what I had to say and gave me his attention. He listened for feminity, not for the content of my sentences. I felt so frisky and special. I wanted to scream, “I’m about to be a faggot” at the top of my lungs. My heart raced, and my skin went cold with anticipation. He walked me to my car around the corner and told me to follow him, back to his house, where we could be alone and try all the things I’d been wanting to try. He walked a few steps, turned back and embraced me, out of view of the club. He put his hands on my waist and leaned in for a kiss. I obliged. I closed my eyes and felt his scratchy stubble and his searching lips, until they met mine. He leaned in and pinched my ass just a little bit harder. He kissed me more, all over my face and rubbed my back up and down. I could feel his hard erection pressed up against mine. He traced the elastic waistband of my boxers and then slid a finger in to make sure I was wearing something sexier underneath. With that, he walked to his car, and I followed him through the back streets to his little suburban home.
He waited for me in his driveway, opened the door of my car for me and helped me out, took my hand and escorted me inside. I grabbed a big purse I’d brought with a few sexy items in it. When we were safely inside, I closed the door behind me and just stood there. He didn’t say a word, but simple walked up to me, kissed me and unzipped my fly. With both hands cradling my head, he kissed me. Then he worked a hand down and pushed my jeans down and then my boxers. I stepped out of them and stood there awkwardly in my red lace panties. I was finally showing off my pantied ass for a big strong man and I’d loved it. So did he. He ran his finger tips along the seams and across the silky backside. He gave my ass a couple of squeezes and a gentle pat, then he sat down on the couch and just gazed at me. So I put on the heels I’d brought and walked back and forth for him, as ladylike as I could. I added lipstick and blew him a few kisses. I hooked a bras in the front and turned in around and slipped my arms into the loops. That was a enough. One day, I wanted to do my makeup and really get fixed up, but not tonight. There wasn’t time. The feeling was too intense and the urges too strong for all of that. I’d been denying these fantasies for too many years and I was tired of it and I wasn’t afraid anymore. I wanted to be the center of attention and a thing of beauty. I wanted a lover who could take the lead and tell me what to do. I wanted to be fondled and fucked by a big strong man. I wanted him to have his way with me. I was going through with it tonight and I was gonna take it up the ass.
I bent forward and kissed him on the cheek and sat between his legs on the floor. He rubbed my shoulders and my hair. I bit at the seams of his denim jeans with my teeth and then opened up, flared my nostrils and took in the aroma of manhood. I lingered there and then slowly slipped down his the jeans. I could see his big print through his white briefs and I pressed my lips against it. When I leaned back and felt his hard tent pitching against my neck. I closed my eyes and felt the warmth and the pulsing against my ear. The smell of his dick was all around me. I closed my eyes and just rubbed my face all of over the cotton cloth and the hard tool below.
I knew that the next step was to turn and chug some cock, but I was getting scared again and I needed a few minutes to collect myself. Just what exactly had I gotten myself into? This was no lady boy. This was a real man, who could really overpower me if he got too excited. He could wrestle me to the ground, pin me down and drive his phallus right through me. Once he got moving, he was not going to want to stop. He’d cover me in lube and just go to town. I’d be laying on my stomach with an arched back and he’d be rubbing and pinching my tits with his hands. I’d be whining and squealing and squirming and getting all sweaty.
My heart would be racing and I’d be panting and short of breath and there’d be no escaping. Just then, I heard a fim voice that snapped me out of my reverie. “Time to put it in your mouth sissy.” and then as if to reassure me, “You can do it you little fag. You’re ready for a dick aren’t you?.” I was embarrassed and ashamed and some part of me wanted to stand up and walk out and go back to my masculine life, but I also longed for tight jeans, and femmy blouses, and skimpy lacy lingerie. I could cook and clean and do laundry and suck dick every day in a little apron. I turned and leaned my head against his inner thigh and looked up at him submissively and he ran his fingers through my hair again. Then out of nowhere he took his semi-hard cock and bopped me in the nose with it. I smiled and started to chase it around with my tongue. At that moment I realized that I was falling right into my new role and I was pleased with myself.
I kiss his balls and his thighs and the base of his shaft. I stroke him and lick my way up the shaft. Finally I close my eyes take his cock deep in my mouth and explore it’s head with my tongue. He likes that and he smiles and I keep going. He chokes me a little and I keep going and he does it again. The third time, he grabs the back of my neck and forces his cock down my throat. I’m overpowered and tearing up. I feel so feminine this way. I look up and he slaps me across the face. He holds me by the chin, peering down into my eyes and slaps me harder. I start to shake and cry. I’m sobbing now and tears are rolling down my cheeks. He shoves the cock back in my mouth and I suck with everything I’ve got. I’m tingling all over and my tongue goes back and forth against the underside of his penis. Now he lifts me onto couch and I’m sideways on it, almost fetal. I’m nursing away on his meat and he spanks me on my red-pantied bottom. He slips his hand inside the panties and starts exploring. He licks his finger and makes circles around my asshole with it. That feels great! He pulls me up and puts me right over his knee and really spanks me good. “You lit-tle faggot he are doing such a good job” I get scared and filled with adrenaline. I am gonna take it so hard up the ass that I’ll walk funny. He spanks some more and I cry like a girl and the sound of my gay little cries makes me even harder. I am so glad I’m going through with this. I guess I was just a little bitch all along. I tighten up with each spank and then go limp over his knees. He cups my butt and finger tips find their way to my anus, bumping rhythmically against it though the satin. I’m sniffling back the tears. He hauls back his palm and spanks again and my flight impulse kicks in. I skamper down onto the floor head first and lay there crumpled up panting for air.
He stands up and lording over me, stepping out of his jeans and flinging his shirt across the room. He kneels and gets down on all fours and crawls towards me. I spring forward and he pounces and suddenly that big dick is against my ass. I enveloped in a warm blanket of manhood, hairy chest against my back. One of his hands is on my stomach and the other is on the small of my back. There is more grinding now and more kisses, this time on the ears. I purr and coo softly and grind back to meet him. Everything is going even better than planned and I’m definitely gonna be getting penetrated soon. There’ll be condoms and lube to find and it’ll take a lot the first time. It’ll take a while to loosen me up to where I need to be. That’s something I’m looking forward to. I want to be a good fuck someday and not just in a virginal sort of way, so work that thing loose big boy! As for tonight, I’ll cry and whimper and sob so much. It’ll hurt, but I’ll love it. He’ll thrust in and out and in again. “Ahh” that thrust was deep. “Ah Aaahh” That one was even deeper. A high pitched squeal will mean pull it out and add some lube. How can I ever wear anything but panties after this. I willingly set up a date with another man and now he’s turning my out something fierce. I’m imagining the way I’ll walk when he’s done pounding me and I’m seeded. It’ll be more of a sashay from now on. He’s getting sweatier and breathing harder now and I just slosh back and forth on rug like a rag mop. He stabs with purpose now, and grunts with each thrust. Finally he holds it in there real deep and shoots his load, filling the head of the condom, somewhere way up in my canal. When he pulls out and turns over, I embrace him. I kiss his face and neck and run my fingers all over his back. He rocks his hips against me and and grinds out his last drops. He reaches a finger down and inserts it in my anus and I grip it tight and cum all over my belly. He relaxes himself and just lays on me, and I feel the fresh cum mixing with his belly and chest hair as he looks into my eyes. Then he collapses and I feel his hot breath against my neck as he winds down. Finally, he lays next to me and I can’t help but clean up all that salty cum on him with my tongue. I better put those panties back on while he’s asleep and get dolled up as best I can. It’s going to be a long night.
Jeannie
- 25.09.2020
- 30
- 0
