I've been a wannabe cuckold all my life. I plan to kind of tell my sexual life story in this threat, relationship by relationship. Hope someone else enjoys.
Part 1.1
I was a late bloomer. I grew up catholic and imposed strongly on myself a life of chastity. I was nothing but a hypocrite, however. Being chaste on the outside, but inside craving depravity and having all kinds of messed up fantasies.
First serious girlfriend
I was nineteen years old, and never even had a real kiss. I had a couple opportunities, but always walked away - pretending it was on some moral high ground. In my head though, I had fucked almost every woman I ever met.
I was at my friend J.'s house. I went to college near my hometown, and he lived about 45 minutes from my dorm. (Maybe I'll make another thread of crazy dorm stories - mostly involving roommates and neighbors, not me though). He invited his female friend B. over. He had talked about her a lot and told me he had been talking to her about me. I never met her before. She was at another friend's house, N. and he came by with her. She stepped out of the van and I saw right away she was just my body type. She was thick. Not fat, just a little extra meat on her bones, nice perky tits and big booty. She had milky white skin, long blond hair, and ruby red lips. I almost had a hardon just looking at her.
The four of us hung out and talked together. I gave her a lot of looks while she was there. I looked her body up and down. She smiled at me lot. I didn't like that she smoked, but I could overlook that. I was still a bit shy at this point, so I didn't make any real advances. When she said she had to go back home, J. suggested I give her a ride back home. We talked a little on the way, just small talk. She was 18, but still living in her parent's trailer, looking for a job and her own place. I dropped her off and headed back to J.'s house. When I got there J. and N. were laughing. I asked what was up and why were they looking at me that way. J. was like "Dude, B. called as soon as you dropped her off and did nothing but tell me how much she likes you." He handed me the phone and dialed her number. We had an awkward conversation about how we liked eachother and I eventually asked her on a date. We set it for tomorrow. I had to get back, I had class in the morning.
The next day, I came by to pick her up as soon as my last class was over. She wanted to go to J.'s house for a little while. We watched a couple movies there. At one point she went into his room and talked to him for a while while I was in the living room. I wasn't sure what they were talking about, but I could tell it had to do with me. We then headed out in my car. J. and B. lived out in the country and we didn't feel like driving back to down, so we just found a back road and parked it. We got in the back seat of my car and cuddled together, listened to music and talked. I ran my fingers through her hair, rubbed her shoulders. Lots of fun stuff, but nothing intense. We eventually got to the topic of sex. She basically said she knew I was a virgin - J. hadn't specifically said so, but she could tell. She said she was afraid to tell me something. I told her go ahead. She confessed to me that she was not a virgin. I told her I knew I was a late bloomer, but I know reality is that most women my age are no longer virgins. She told me she just lost it not long ago, though.
She was hanging out with her friends and a couple of their boyfriends. They started talking about sex, and she got a little uncomfortable. They were sharing and swapping stories and she was quiet. One of her friends then turned to her and asked her what her best time was like. She turned red and didn't say anything. Her friends prodded her until finally she said she was still a virgin. They were shocked. One of her friend said she didn't know what she was missing, she really had to try it. Then another girl suggested B. should have sex with her boyfriend. He was an older guy, about 25. She thought he was attractive but it was a little weird that her friend would suggest that. Then she said here, we'll leave and let you two get acquainted. They started talking and he said they had an open relationship, and he'd really like to. She nervously said she couldn't do it right there. He said he knew a spot and led her out to an abandoned trailer. He laid her down on a bed in the back and undressed her. She just kind of laid there as he undressed and laid down on top of her. It felt good as he slid it in at first. There was a little pain and it was tight but she was enjoying it. They kissed and she wrapped her hands around him. Then she looked towards the window. All of her friends were watching. She started to freak out. He told her to just relax... she laid back and took it until he came inside of her. Her friends were giggling outside. He dressed himself and walked out and her friends rushed in to ask her how it was. She was totally red and incredibly embarrassed and said she didn't want to talk about it.
She told me she decided after that she regretted it and was going to be a "secondary virgin." I kind of chuckled, remembering those high school sex ed classes that mentioned it. She got a little mad and said "no, i'm serious, I'm saving myself for the right guy now."
We changed the subject and laid there for a while. I was nervous and didn't really make any moves. It got late and I brought her back. That night while I was in bed, I couldn't stop thinking about her story. I imagined her getting fucked with all her friends watching and jacked of thinking about his dick going in and out of her. This was the first time I jacked of thinking about someone else with a woman. As I came, I convinced myself I was just wishing I was in his spot.
We had a few more dates. Usually about the same. Parked somewhere on a country road. We eventually kissed. She started with cute little kisses all over my face, then pressed her lips to mine and opened her mouth, pushing her tongue into mine. I was a long, deep passionate kiss like I never experienced before. She had a long tongue and it probed my mouth and went back to my throat as we rubbed all over our bodies. From that point on, we had heavy makeout sessions in the back of that car and always steamed the windows over. Most of the time, while we were laying together I had a huge hardon. I knew she HAD to feel it as she laid against me. Sometimes her mouth tasted a little funny to me, but I didn't think much of it. I asked her about her first time a few times more. She gave me more details, and seemed to admit more and more that she actually enjoyed the experience more than regretted it. Since I was rock hard and further imagining her getting fucked, this all added up to one hell of a cock tease. It didn't help that we often hung out at J.'s before we went out, and we'd sometimes watch a video from his porno collection.
As our makeout sessions got heavier, she seemed to deliberately rub her crotch against mine, making me even harder. Our hands wandered all over our bodies. We took our shirts off, touching skin to skin. One day, I decided to go for it, and undid her bra, slid my tongue around her body, and around her nipples, pressed my lips to one and sucked on it. I remember her moaning in pleasure and pulling me tight to her.
The next day she called me. She said I went to far and she couldn't handle it. I said she didn't try to stop me. She said yes she did, didn't I feel her trying to push me away? I said it felt like the opposite to me. She said no and that she needed to break it off. I was devastated. I couldn't believe it.
The next day, I talked to J. about it. He laughed and said it didn't make any sense. He had came on her tits earlier that day. I said "What?!" He said yeah, she was sucking his cock and he pulled out and came on her tits. I said "excuse me?" He said "I thought you knew, Her and I have been friends with benefits for a while. You mean she didn't tell you?" I was in shock. "You mean you guys were doing stuff all along and just continued even when I started going out with her?" He said he thought we had an open relationship.
I was pissed. I left, went back to my dorm and cried, hoping my roommate wouldn't walk in on me. That night, I couldn't get the image out of my head - her lips wrapped around his cock, bobbing her head up and down until he pulls out and cums on her tits. I knew exactly what his dick looked like - he loved getting naked when *****, so it was a very detailed vision. I started jacking of despite myself - creamed a large load into my underwear that night. In the morning, I couldn't believe I had jacked off to that. The next night I fantasized about it again...and the night after. Next, I imagined the cum still being on her tits while I licked and sucked on them, cleaning it off of her. I was actually enjoying the thought of her being with him.
Part 1.1
I was a late bloomer. I grew up catholic and imposed strongly on myself a life of chastity. I was nothing but a hypocrite, however. Being chaste on the outside, but inside craving depravity and having all kinds of messed up fantasies.
First serious girlfriend
I was nineteen years old, and never even had a real kiss. I had a couple opportunities, but always walked away - pretending it was on some moral high ground. In my head though, I had fucked almost every woman I ever met.
I was at my friend J.'s house. I went to college near my hometown, and he lived about 45 minutes from my dorm. (Maybe I'll make another thread of crazy dorm stories - mostly involving roommates and neighbors, not me though). He invited his female friend B. over. He had talked about her a lot and told me he had been talking to her about me. I never met her before. She was at another friend's house, N. and he came by with her. She stepped out of the van and I saw right away she was just my body type. She was thick. Not fat, just a little extra meat on her bones, nice perky tits and big booty. She had milky white skin, long blond hair, and ruby red lips. I almost had a hardon just looking at her.
The four of us hung out and talked together. I gave her a lot of looks while she was there. I looked her body up and down. She smiled at me lot. I didn't like that she smoked, but I could overlook that. I was still a bit shy at this point, so I didn't make any real advances. When she said she had to go back home, J. suggested I give her a ride back home. We talked a little on the way, just small talk. She was 18, but still living in her parent's trailer, looking for a job and her own place. I dropped her off and headed back to J.'s house. When I got there J. and N. were laughing. I asked what was up and why were they looking at me that way. J. was like "Dude, B. called as soon as you dropped her off and did nothing but tell me how much she likes you." He handed me the phone and dialed her number. We had an awkward conversation about how we liked eachother and I eventually asked her on a date. We set it for tomorrow. I had to get back, I had class in the morning.
The next day, I came by to pick her up as soon as my last class was over. She wanted to go to J.'s house for a little while. We watched a couple movies there. At one point she went into his room and talked to him for a while while I was in the living room. I wasn't sure what they were talking about, but I could tell it had to do with me. We then headed out in my car. J. and B. lived out in the country and we didn't feel like driving back to down, so we just found a back road and parked it. We got in the back seat of my car and cuddled together, listened to music and talked. I ran my fingers through her hair, rubbed her shoulders. Lots of fun stuff, but nothing intense. We eventually got to the topic of sex. She basically said she knew I was a virgin - J. hadn't specifically said so, but she could tell. She said she was afraid to tell me something. I told her go ahead. She confessed to me that she was not a virgin. I told her I knew I was a late bloomer, but I know reality is that most women my age are no longer virgins. She told me she just lost it not long ago, though.
She was hanging out with her friends and a couple of their boyfriends. They started talking about sex, and she got a little uncomfortable. They were sharing and swapping stories and she was quiet. One of her friends then turned to her and asked her what her best time was like. She turned red and didn't say anything. Her friends prodded her until finally she said she was still a virgin. They were shocked. One of her friend said she didn't know what she was missing, she really had to try it. Then another girl suggested B. should have sex with her boyfriend. He was an older guy, about 25. She thought he was attractive but it was a little weird that her friend would suggest that. Then she said here, we'll leave and let you two get acquainted. They started talking and he said they had an open relationship, and he'd really like to. She nervously said she couldn't do it right there. He said he knew a spot and led her out to an abandoned trailer. He laid her down on a bed in the back and undressed her. She just kind of laid there as he undressed and laid down on top of her. It felt good as he slid it in at first. There was a little pain and it was tight but she was enjoying it. They kissed and she wrapped her hands around him. Then she looked towards the window. All of her friends were watching. She started to freak out. He told her to just relax... she laid back and took it until he came inside of her. Her friends were giggling outside. He dressed himself and walked out and her friends rushed in to ask her how it was. She was totally red and incredibly embarrassed and said she didn't want to talk about it.
She told me she decided after that she regretted it and was going to be a "secondary virgin." I kind of chuckled, remembering those high school sex ed classes that mentioned it. She got a little mad and said "no, i'm serious, I'm saving myself for the right guy now."
We changed the subject and laid there for a while. I was nervous and didn't really make any moves. It got late and I brought her back. That night while I was in bed, I couldn't stop thinking about her story. I imagined her getting fucked with all her friends watching and jacked of thinking about his dick going in and out of her. This was the first time I jacked of thinking about someone else with a woman. As I came, I convinced myself I was just wishing I was in his spot.
We had a few more dates. Usually about the same. Parked somewhere on a country road. We eventually kissed. She started with cute little kisses all over my face, then pressed her lips to mine and opened her mouth, pushing her tongue into mine. I was a long, deep passionate kiss like I never experienced before. She had a long tongue and it probed my mouth and went back to my throat as we rubbed all over our bodies. From that point on, we had heavy makeout sessions in the back of that car and always steamed the windows over. Most of the time, while we were laying together I had a huge hardon. I knew she HAD to feel it as she laid against me. Sometimes her mouth tasted a little funny to me, but I didn't think much of it. I asked her about her first time a few times more. She gave me more details, and seemed to admit more and more that she actually enjoyed the experience more than regretted it. Since I was rock hard and further imagining her getting fucked, this all added up to one hell of a cock tease. It didn't help that we often hung out at J.'s before we went out, and we'd sometimes watch a video from his porno collection.
As our makeout sessions got heavier, she seemed to deliberately rub her crotch against mine, making me even harder. Our hands wandered all over our bodies. We took our shirts off, touching skin to skin. One day, I decided to go for it, and undid her bra, slid my tongue around her body, and around her nipples, pressed my lips to one and sucked on it. I remember her moaning in pleasure and pulling me tight to her.
The next day she called me. She said I went to far and she couldn't handle it. I said she didn't try to stop me. She said yes she did, didn't I feel her trying to push me away? I said it felt like the opposite to me. She said no and that she needed to break it off. I was devastated. I couldn't believe it.
The next day, I talked to J. about it. He laughed and said it didn't make any sense. He had came on her tits earlier that day. I said "What?!" He said yeah, she was sucking his cock and he pulled out and came on her tits. I said "excuse me?" He said "I thought you knew, Her and I have been friends with benefits for a while. You mean she didn't tell you?" I was in shock. "You mean you guys were doing stuff all along and just continued even when I started going out with her?" He said he thought we had an open relationship.
I was pissed. I left, went back to my dorm and cried, hoping my roommate wouldn't walk in on me. That night, I couldn't get the image out of my head - her lips wrapped around his cock, bobbing her head up and down until he pulls out and cums on her tits. I knew exactly what his dick looked like - he loved getting naked when *****, so it was a very detailed vision. I started jacking of despite myself - creamed a large load into my underwear that night. In the morning, I couldn't believe I had jacked off to that. The next night I fantasized about it again...and the night after. Next, I imagined the cum still being on her tits while I licked and sucked on them, cleaning it off of her. I was actually enjoying the thought of her being with him.