Strap On Jenny
- 3 years ago
- 38
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Strap-on Sex free porn video
A while back I dated a woman that when we first got together was shy and introverted. We met on the "old" Yahoo Messenger where you could go into different rooms and chat and look at cams. At first she would only let me see from her neck up. Her reasoning was that she was ugly and didn't like her body. I finally got her to show me the rest of herself and was immediately turned on. She was a BBW and had a nice big ass and 36DD tits. When I told her how she had affected me she didn't believe me. Well, our conversations went on for a couple weeks and finally I let her talk me into coming over to my place. It was already after 10PM and had just finished storming when she got to my house. We had a glorious first date.....we went to WalMart. We walked around in the store for a while.....and during the entire time we were groping and touching the other. We finally left and went back to my place. I used our little trip as an excuse to set off some bug bombs (neighbor's cats would get under my house and leave their fleas) so we sat in her car and talked. After a while we moved to the back seat and clothes came off. As we kissed my hands massaged her tits and pinched her nipples and her hand went straight to my cock. I moved one hand to her panties (her jeans were on the floor board next to mine) and when I slipped my hand in she was soaking wet. I slid 3 fingers easily into her and started fingering her. She was pouring juice all over my fingers and her car seat. Just as her breathing was starting to get harder she pulled my hand away and pushed me back and moved her head between my legs and took my cock in her mouth. It took everything I had NOT to cum....my cock hadn't been in a woman's (or man's) mouth in a while. My ex-wife REFUSED to suck my cock......said it made her want to puke (and missionary was the ONLY position she would let me fuck her.....except the one time out in the back yard when she was on her hands and knees working in her flower bed.....but that's another story). Well "Jenny" (obviously NOT her real name) was licking and sucking my cock like a vacuum. I finally had to move her away because I didn't want to cum so quick. I had her lay back and dove into her pussy tongue first and licked and sucked her clit. She grabbed my head and ground her pussy against my face and held in a scream and came....and gave me nearly a mouthful of her juice. I moved up and slid my cock into her still spasming pussy and started fucking her slow at first, but picked up speed when she started pushing against me. I couldn't hold back and came inside her. I know what you're thinking......we took a BIG chance.....fucking a stranger without protection.......and you're right. There was no chance of me getting her pregnant because of a medical condition I have I am sterile.....shooting blanks.
We got dressed and sat and talked for a while. Later that day we went to the county health department ($5 STD tests) and 3 days later got a clean bill of health.
Jenny and I started "dating" and soon she was staying part-time at my place and the other times with her daughter that lived 40 miles away. Jenny had 4 k**s ranging in age from 26 to 9. She was 42 and I was 35. Over the next few months Jenny learned of my likes, dislikes and fetishes. She was fascinated with my love of watching women piss and shit (especially outside and in risky locations), giving and receiving enemas, toys, being bi and my love of cross-dressing. She said her ex-husband had her piss on him a couple times but she didn't care for it and didn't think she could ever shit on anyone. I explained that I didn't want it on me....I just loved watching it happen. She said she would have to think about the enemas. She also loved toys and brought her's with her. She had a "standard" 7" cock-shaped vibrator and silver egg. She admitted that she always wanted to see a man dressed as a woman, so I gave her the opportunity. Now I wasn't then and definitely not now passable but the last time I dressed for someone else he told me that from the neck down I looked sexy (I had and still have a moustache). I had Jenny sit in the living room and I went to the bedroom to change. I had her close her eyes and I sat down across from her. When I had her open her eyes she just sat there for a full minute.....eyes wide and mouth open. When I say the look on her face, my first thought was "Oh well.....she's fixing to leave"......well I was wrong. She was only wearing a gown and panties.....and as she sat there staring at me, one hand went to her tits and the other went to her pussy. "Stand up and let me see what you look like", she told me. So I stood up and did a slow turn for her. I was wearing a white see-through blouse, black bra, navy blue mini skirt, black lace panties and black stockings (I HATE pantyhose and thongs!!!) and I didn't have a wig or make-up at that time. She sat there pinching her nipples through her gown and rubbing her pussy, she now had her hand inside her panties. She took the hand that was on her tit and started caressing my ass under my skirt but through my panties. Then she started rubbing my cock through my panties and I heard her breathing get a little faster and deeper. I felt her shiver and then she stood up, took my hand and led me to the bedroom. She had me get on the bed on my hands and knees. I felt her lift my skirt and start kissing my ass cheeks through my panties. She then slid my panties off my ass and I then I felt her kisses on my bare skin. She then did something I have done but it was the first time I had it done to me.....she tongued my asshole. I nearly shot my cum on the sheets when I felt her tongue push into me. She had me on the edge for several minutes.....her tongue going deep into me, then she stopped, told me to stay just like I was and felt her get off the bed. She was gone for only a minute, enough for the load of cum that was building to back off a bit when I felt her spread my ass cheeks and I felt the head of her vibrator pushing against my asshole. I relaxed my ass and felt her vibrator slip into me and she didn't stop pushing until I felt the fingers she was holding the vibrator with on my balls. She pulled it out until just the head was still in me and then pushed it back all the way in. She fucked my ass slow and deep and I could hear her breathing hard. She told me to jerk off while she fucked me so I put a hand on my cock and started stroking in time with her fucking. It only took a minute or so and I told her I was about to cum.....pushed back against her, taking the vibrator all the way in and shooting a huge load all over my hand and the sheets. Then I felt the vibrator shaking in my ass, she was having her own huge orgasm. We decided then and there we were going to buy a strap-on. So the next few days we searched the internet for one that was reasonably priced and not too big. We found one that was about 6” long, 1.5” thick and the base was made with a pair of panties big enough for her and ordered it. About a week later it arrived and we couldn’t wait to try it, but we had her daughter and had to wait. We finally got a weekend to ourselves and opened our package. She immediately went to the bathroom and washed the dildo with soap and water and went to the bedroom. She had me get on my hands and knees and got behind me. She lubed the dildo and fingered some lube into my asshole and helped me to relax. Then she pushed the head of the dildo into me and slid it all the way in. She started out fucking me slow but steadily picked up speed and was soon pounding me. I pushed back against her, taking the dildo deep and causing our skip to make a slapping noise. All of a sudden she started groaning and fell back on the bed shaking and having spasms, her pussy pouring juice. I pulled the panties off her, pushed her legs apart and drove my cock into her still clenching pussy fucking her hard and fast. She came again and I shot my load into her. We fell into a pile on the bed and lay there until we recovered enough to get up. We didn’t do anything else that night or the next few nights because of work and the next weekend we had her daughter with us and couldn’t play. Finally one evening, I had got off work at 10P and had the next 3 days off and she got off at midnight and had a couple days off as well and we planned on playing. One fantasy I had had was that I wanted to be dressed and have her fuck me with the strap-on out in the yard. So before she left for work I slipped the strap-on into her purse with a note that said, “Be ready to use this when you get home.” So before she got home, I put on a pair of black stockings, black panties and bra under a tan skirt that had belonged to my ex-wife and I made into a mini by cutting 6” off the bottom and the striped blouse my ex used to wear with the skirt, went outside and waited on her to get home. When she pulled up into the drive way she saw me sitting on the tailgate of my truck. She got out of her car and walked over to me. She didn’t say anything just pulled me to her and started kissing me. She ran her hand under my skirt and rubbed my legs and crotch. She had me stand up and continued kissing me and letting her hands roam around under my skirt pressing her crotch against me so I could feel the strap-on under her jeans. She pulled back and said, ”You know what I want.” I got on my knees in front of her and unzipped her jeans took out the dildo and started sucking on it like I was giving her a blowjob. She put her hands on the back of my head and fucked my mouth and throat. I felt her let go of my head and looked up and she was squeezing her nipples through her shirt, but she kept her hips moving, fucking my mouth. She then pulled me up, spun me around, pulled my skirt up and panties down and after putting lube on the dildo, shoved it into my asshole. She didn’t play around, she fucked my ass hard and deep. She bent me over the hood of her car, grabbed my hips and gave me everything she had. She stopped and had me sit on the fender and lay back and entered me again. She had pulled her shirt up and taken her tits out of her bra and was pinching her nipples. She let out a loud moan and had an intense orgasm. She moved back, pulling the dildo out of me and took off her shirt and bra. Then she pulled off her shoes and pulled off her jeans and the panty/dildo and stood there in the front yard naked. I stripped off my things and had her lay on the hood of the car and licked and tongue fucked her pussy till she came again. Then I got her off the car and onto her hands and knees on the ground, got behind her and slid my cock into her soaking wet pussy. I fucked her as hard as she had fucked me. She started to cum again and I was ready to shoot when a car passed by the end of the driveway. I guess the thought of being watched got to her because she came hard and I shot my load in her pussy. We fucked 2 more times that night and then crashed into a deep, exhausted sleep. The next day she had to go to her daughter’s house and I stayed home because I had yard work to do. She called later that evening saying she was on the way home by herself. I put on a pair of white panties and stockings and a cami top. I was in the kitchen cooking supper when she got home and she didn’t say a word she just came into the kitchen and ground her crotch against my ass. I could feel the dildo under her shorts and let her do as she pleased. She pulled her shorts down and then pulled my panties down and spit lubed the dildo and pushed it into me. She fucked me right there at the kitchen counter until she had an orgasm then pulled my panties back up and told me to finish cooking. While we were eating she admitted that she came everytime she fucked me with the strap-on, that there was something in doing it that made her cum. I was feeling adventurous so after we finished eating and let our meal digest a little, we stripped off and went outside. I brought a blanket and lay on it making out at first. Then she sucked my cock and licked my ass then I eat her pussy and licked her ass until she came. Then we fucked in a few different positions until we both we satisfied, usually with me banging her pussy from behind. We ran errands the next day and I got my first ever road blowjob. We were coming home from the store and she leaned over, put her head in my lap, opened my jeans, took out my cock and started sucking me as I drove. A few drivers of the taller vehicles that passed us blew their horns when they saw what was happening. I took a back way home and on a deserted stretch of road pulled off to the shoulder. I had her get out, bent her over the trunk lid and fucked her right there on the side of the road. Probably the most daring time we fucked was when we stayed at my parent’s house for Hurricane Ivan. After the storm had passed, the road to my house was still blocked and there was no power so we stayed at my parent’s along with of course my parents, her daughter, the 2 uncles I had lived with a few years before, my sister and her 2 k**s. After everyone else had gone to sleep we sneaked outside to smoke and started teasing each other. We both got worked up and knew we had to take care of things so we got behind the cars in the driveway, she got on her hands and knees and I got on my knees behind her. I pulled her shorts and panties down and my shorts and underwear down and fucked her right there in my parent’s drive way. When she started to cum I pulled out, leaned down and shoved my tongue into her ass making her cum harder. She was having a hard time being quiet but I straightened up and slid my cock back into her and in just a few thrusts shot my load into her. Just as we were standing up, the front door opened and one of my uncles came out to smoke.
We stayed together until I fell for a co-worker and broke up with her. Even though we had great sex, shared a passion for experimentation she was just not right for me. We didn’t “click”. The woman I left her for turned out to be a psychotic bitch from Hell and that was 3 years of my life I’ll never get back and to this day wish I hadn’t done it.
She moved after our break up and got with a guy she met here then they moved to S.Carolina. She came back to town when her father passed away and she stayed with me for a while. I thought we would pick up where we left off, but it wasn’t to be. We played and had some great sex, including fucking in WalMart one night. She was wearing a summer dress and flipflops and nothing else. She had been teasing me by bending over so I could see her tits swinging free under her dress or by pulling up the hem and flashing her ass and pussy. I was hard as a rock and she was enjoying teasing me and she would rub my crotch with her hand or push between me and the shelf, rubbing her ass against me until I couldn’t take it anymore. We were in the automotive department and she was in the process of flashing her ass at me for the 5th or 6th time when I unbuttoned and unzipped my jeans (I had stopped wearing underwear when we went out anywhere to ease access) moved behind her bent her over and slid my cock into her pussy. There we were, next to the windshield wipers her with the hem of her dress up over her ass and me with my pants hanging off my ass fucking away. Neither of us came but it was enough to show her not to tease me too often. We finished our shopping and as we put the stuff in the car she bent over to put a bag in the back of the van she was driving I lifted her dress again and opened my pants and fucked her pussy until we both came. We went out to eat the next night and she gave me a hand job under the table and I fingered her. She left one day while I was at work. I came home and found a note saying that she was more in love with the guy she was with in S. Carolina than she realized and even though we were good sex friends she couldn’t see us in a permanent relationship. I haven’t seen or heard from her since.
We got dressed and sat and talked for a while. Later that day we went to the county health department ($5 STD tests) and 3 days later got a clean bill of health.
Jenny and I started "dating" and soon she was staying part-time at my place and the other times with her daughter that lived 40 miles away. Jenny had 4 k**s ranging in age from 26 to 9. She was 42 and I was 35. Over the next few months Jenny learned of my likes, dislikes and fetishes. She was fascinated with my love of watching women piss and shit (especially outside and in risky locations), giving and receiving enemas, toys, being bi and my love of cross-dressing. She said her ex-husband had her piss on him a couple times but she didn't care for it and didn't think she could ever shit on anyone. I explained that I didn't want it on me....I just loved watching it happen. She said she would have to think about the enemas. She also loved toys and brought her's with her. She had a "standard" 7" cock-shaped vibrator and silver egg. She admitted that she always wanted to see a man dressed as a woman, so I gave her the opportunity. Now I wasn't then and definitely not now passable but the last time I dressed for someone else he told me that from the neck down I looked sexy (I had and still have a moustache). I had Jenny sit in the living room and I went to the bedroom to change. I had her close her eyes and I sat down across from her. When I had her open her eyes she just sat there for a full minute.....eyes wide and mouth open. When I say the look on her face, my first thought was "Oh well.....she's fixing to leave"......well I was wrong. She was only wearing a gown and panties.....and as she sat there staring at me, one hand went to her tits and the other went to her pussy. "Stand up and let me see what you look like", she told me. So I stood up and did a slow turn for her. I was wearing a white see-through blouse, black bra, navy blue mini skirt, black lace panties and black stockings (I HATE pantyhose and thongs!!!) and I didn't have a wig or make-up at that time. She sat there pinching her nipples through her gown and rubbing her pussy, she now had her hand inside her panties. She took the hand that was on her tit and started caressing my ass under my skirt but through my panties. Then she started rubbing my cock through my panties and I heard her breathing get a little faster and deeper. I felt her shiver and then she stood up, took my hand and led me to the bedroom. She had me get on the bed on my hands and knees. I felt her lift my skirt and start kissing my ass cheeks through my panties. She then slid my panties off my ass and I then I felt her kisses on my bare skin. She then did something I have done but it was the first time I had it done to me.....she tongued my asshole. I nearly shot my cum on the sheets when I felt her tongue push into me. She had me on the edge for several minutes.....her tongue going deep into me, then she stopped, told me to stay just like I was and felt her get off the bed. She was gone for only a minute, enough for the load of cum that was building to back off a bit when I felt her spread my ass cheeks and I felt the head of her vibrator pushing against my asshole. I relaxed my ass and felt her vibrator slip into me and she didn't stop pushing until I felt the fingers she was holding the vibrator with on my balls. She pulled it out until just the head was still in me and then pushed it back all the way in. She fucked my ass slow and deep and I could hear her breathing hard. She told me to jerk off while she fucked me so I put a hand on my cock and started stroking in time with her fucking. It only took a minute or so and I told her I was about to cum.....pushed back against her, taking the vibrator all the way in and shooting a huge load all over my hand and the sheets. Then I felt the vibrator shaking in my ass, she was having her own huge orgasm. We decided then and there we were going to buy a strap-on. So the next few days we searched the internet for one that was reasonably priced and not too big. We found one that was about 6” long, 1.5” thick and the base was made with a pair of panties big enough for her and ordered it. About a week later it arrived and we couldn’t wait to try it, but we had her daughter and had to wait. We finally got a weekend to ourselves and opened our package. She immediately went to the bathroom and washed the dildo with soap and water and went to the bedroom. She had me get on my hands and knees and got behind me. She lubed the dildo and fingered some lube into my asshole and helped me to relax. Then she pushed the head of the dildo into me and slid it all the way in. She started out fucking me slow but steadily picked up speed and was soon pounding me. I pushed back against her, taking the dildo deep and causing our skip to make a slapping noise. All of a sudden she started groaning and fell back on the bed shaking and having spasms, her pussy pouring juice. I pulled the panties off her, pushed her legs apart and drove my cock into her still clenching pussy fucking her hard and fast. She came again and I shot my load into her. We fell into a pile on the bed and lay there until we recovered enough to get up. We didn’t do anything else that night or the next few nights because of work and the next weekend we had her daughter with us and couldn’t play. Finally one evening, I had got off work at 10P and had the next 3 days off and she got off at midnight and had a couple days off as well and we planned on playing. One fantasy I had had was that I wanted to be dressed and have her fuck me with the strap-on out in the yard. So before she left for work I slipped the strap-on into her purse with a note that said, “Be ready to use this when you get home.” So before she got home, I put on a pair of black stockings, black panties and bra under a tan skirt that had belonged to my ex-wife and I made into a mini by cutting 6” off the bottom and the striped blouse my ex used to wear with the skirt, went outside and waited on her to get home. When she pulled up into the drive way she saw me sitting on the tailgate of my truck. She got out of her car and walked over to me. She didn’t say anything just pulled me to her and started kissing me. She ran her hand under my skirt and rubbed my legs and crotch. She had me stand up and continued kissing me and letting her hands roam around under my skirt pressing her crotch against me so I could feel the strap-on under her jeans. She pulled back and said, ”You know what I want.” I got on my knees in front of her and unzipped her jeans took out the dildo and started sucking on it like I was giving her a blowjob. She put her hands on the back of my head and fucked my mouth and throat. I felt her let go of my head and looked up and she was squeezing her nipples through her shirt, but she kept her hips moving, fucking my mouth. She then pulled me up, spun me around, pulled my skirt up and panties down and after putting lube on the dildo, shoved it into my asshole. She didn’t play around, she fucked my ass hard and deep. She bent me over the hood of her car, grabbed my hips and gave me everything she had. She stopped and had me sit on the fender and lay back and entered me again. She had pulled her shirt up and taken her tits out of her bra and was pinching her nipples. She let out a loud moan and had an intense orgasm. She moved back, pulling the dildo out of me and took off her shirt and bra. Then she pulled off her shoes and pulled off her jeans and the panty/dildo and stood there in the front yard naked. I stripped off my things and had her lay on the hood of the car and licked and tongue fucked her pussy till she came again. Then I got her off the car and onto her hands and knees on the ground, got behind her and slid my cock into her soaking wet pussy. I fucked her as hard as she had fucked me. She started to cum again and I was ready to shoot when a car passed by the end of the driveway. I guess the thought of being watched got to her because she came hard and I shot my load in her pussy. We fucked 2 more times that night and then crashed into a deep, exhausted sleep. The next day she had to go to her daughter’s house and I stayed home because I had yard work to do. She called later that evening saying she was on the way home by herself. I put on a pair of white panties and stockings and a cami top. I was in the kitchen cooking supper when she got home and she didn’t say a word she just came into the kitchen and ground her crotch against my ass. I could feel the dildo under her shorts and let her do as she pleased. She pulled her shorts down and then pulled my panties down and spit lubed the dildo and pushed it into me. She fucked me right there at the kitchen counter until she had an orgasm then pulled my panties back up and told me to finish cooking. While we were eating she admitted that she came everytime she fucked me with the strap-on, that there was something in doing it that made her cum. I was feeling adventurous so after we finished eating and let our meal digest a little, we stripped off and went outside. I brought a blanket and lay on it making out at first. Then she sucked my cock and licked my ass then I eat her pussy and licked her ass until she came. Then we fucked in a few different positions until we both we satisfied, usually with me banging her pussy from behind. We ran errands the next day and I got my first ever road blowjob. We were coming home from the store and she leaned over, put her head in my lap, opened my jeans, took out my cock and started sucking me as I drove. A few drivers of the taller vehicles that passed us blew their horns when they saw what was happening. I took a back way home and on a deserted stretch of road pulled off to the shoulder. I had her get out, bent her over the trunk lid and fucked her right there on the side of the road. Probably the most daring time we fucked was when we stayed at my parent’s house for Hurricane Ivan. After the storm had passed, the road to my house was still blocked and there was no power so we stayed at my parent’s along with of course my parents, her daughter, the 2 uncles I had lived with a few years before, my sister and her 2 k**s. After everyone else had gone to sleep we sneaked outside to smoke and started teasing each other. We both got worked up and knew we had to take care of things so we got behind the cars in the driveway, she got on her hands and knees and I got on my knees behind her. I pulled her shorts and panties down and my shorts and underwear down and fucked her right there in my parent’s drive way. When she started to cum I pulled out, leaned down and shoved my tongue into her ass making her cum harder. She was having a hard time being quiet but I straightened up and slid my cock back into her and in just a few thrusts shot my load into her. Just as we were standing up, the front door opened and one of my uncles came out to smoke.
We stayed together until I fell for a co-worker and broke up with her. Even though we had great sex, shared a passion for experimentation she was just not right for me. We didn’t “click”. The woman I left her for turned out to be a psychotic bitch from Hell and that was 3 years of my life I’ll never get back and to this day wish I hadn’t done it.
She moved after our break up and got with a guy she met here then they moved to S.Carolina. She came back to town when her father passed away and she stayed with me for a while. I thought we would pick up where we left off, but it wasn’t to be. We played and had some great sex, including fucking in WalMart one night. She was wearing a summer dress and flipflops and nothing else. She had been teasing me by bending over so I could see her tits swinging free under her dress or by pulling up the hem and flashing her ass and pussy. I was hard as a rock and she was enjoying teasing me and she would rub my crotch with her hand or push between me and the shelf, rubbing her ass against me until I couldn’t take it anymore. We were in the automotive department and she was in the process of flashing her ass at me for the 5th or 6th time when I unbuttoned and unzipped my jeans (I had stopped wearing underwear when we went out anywhere to ease access) moved behind her bent her over and slid my cock into her pussy. There we were, next to the windshield wipers her with the hem of her dress up over her ass and me with my pants hanging off my ass fucking away. Neither of us came but it was enough to show her not to tease me too often. We finished our shopping and as we put the stuff in the car she bent over to put a bag in the back of the van she was driving I lifted her dress again and opened my pants and fucked her pussy until we both came. We went out to eat the next night and she gave me a hand job under the table and I fingered her. She left one day while I was at work. I came home and found a note saying that she was more in love with the guy she was with in S. Carolina than she realized and even though we were good sex friends she couldn’t see us in a permanent relationship. I haven’t seen or heard from her since.
Arisha
- 29.01.2023
- 34
- 0
