The life of a wannabe cuckold

[NotEnufMan]

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.

 

[NotEnufMan]

Part 1.2

Part 1.2

A couple weeks later, she called. She said she really missed me and wanted me back. I said OK. I went to pick her up that night, but found she was already at J.'s. I went over to his house, and we hung out for a while as usual, then went out in my car and parked it. As soon as we got in the back seat, she pushed my down and laid on top of me, and the heavy makeout session began. Her mouth had that funny taste again - and suddenly I realized that was the taste of his cock and cum in her mouth! I got an instant hard on. She wiggled her hips up against me, we started dry humping as we made out, our hands all over eachother's bodies - and I couldn't believe it, I came in my pants. I don't know if she felt it, she kept on going like nothing happened. She said "I missed you" I said "I missed you, too."

It continued on like that - she'd already be at J.'s house when I'd pick her up for dates. She had to know I knew at this point, but it was left unspoken. No one said anything about it. She started getting more blatant. I'd walk into J.'s house and they'd both be in his bedroom. After a few minutes, they'd come out. I started hearing noises - him moaning really loud - he'd stop, and a few minutes later they'd come out. We didn't hang out at his place now, we'd go straight to my car. The bitch was getting off on this - and I was, too! I could taste his cum really strongly now, and was imagining his cock in her mouth whenever we made out. I creamed my pants almost every time. She'd smile this evil little smile at me and that would just drive me more nuts. After many more dates, I started to hear them both moaning - it took them longer to get out of his room - and sometimes I didn't taste his cock on her lips. I knew they were fucking. Now I was imagining his dick going in her as we made out - though I had never seen her pussy. We eventually fought over something else and broke up. We never had sex, never even saw each other naked, but she gave me one hell of a mind fuck. I hadn't accepted how much I loved that, yet, though.

 

[Warpt]

Damn, that is the kind of story that dreams are made of...

 

[duke9555]

pray continue

 

[NotEnufMan]

Part 2.1

2 years later, i'm legal drinking age and yet, still a virgin. I had a few attempts at getting laid that got shot down, and one that I stupidly turned down. The internet has matured since my last relationship, and I now have multiple online "relationships" going. One girl in particular, J. was 18 and a Freshman in college - her parents were about 2 hours from my parents. Problem - I go to school 2 hours from my parents, and she goes to school 6 hours from hers!

One day we're talking about vacations, and the stars finally align for us. We're each vising our parents on the same weekend - I had the week before off, she had the week after. She could come up to my apartment (I moved out of the dorms now, had two roomates - and old dorm roomate and and old neighbor). I set off to pick her up from her parents.

This was the first time seeing her in person. I saw a few pictures (a few nude) - but they didn't do her justice. She had a nice perky bubble butt, huge 38DD tits, big lucious lips and curly blond hair. Thick, but not fat, the way I like it ;-) I got there, said hello, we all talked for a little bit, then we jumped in my car and sped off. We got a little way down the road and she asked me to pull off into a park-and-ride lot. It was late, the buses were no longer running in our area, and the lot was empty. I parked the car, and she jumped on me so fast I didn't see it coming. After a short, hot makeout session, she gets back into her seat saying "that's just a little taste of what we're gonna do later."

It was about a 3 hour drive (bypassing my parents) when we got back to my apartment. It was Saturday, and my roomates weren't due back until Sunday night. After having a quick bite to eat, I show her around the apartment, finishing with my bedroom. She shuts the door behind her, pushes me into my desk chair, sits on my lap and starts kissing me all over. I no time, her top was off, I undid her bra, and her huge 44DD tits were slapping me in the face. I immediately began sucking on them, licking them, playing with them with my tongue. She stood up, took off her pants and panties, flinging her panties onto my head. She sat down on my bed, spread her legs wide and said "I want to feel you do to me what you keep talking about online..." I knew right away she was talking about eating her pussy. She knew I was a virgin, but I don't think she knew I had never really done oral, either.

I had began to recognize how I viewed women - above me - and I should do whatever I had to to please them. I immediately got on my hands and knees, crawled over to her, kissed her feet and slowly made my way up one leg, then back to her other foot and up the other leg. "Quit teasing me!" she moaned, and I slid my tongue up her inner thigh, and started lapping her juices off her pussy lips. She was already incredibly wet. As I licked her up and down, she grabbed my head and buried my face into her pussy. I spread her slit and stuck my tongue deep into her pussy hole. She bucked up and down on my face and rubbed her juices all over it. I was realizing two more things... this girl I found was a total FREAK, and I loved eating pussy. I was great on a physical and mental level. I was surprised at how much I loved her taste, and swallowing her juices - and I loved being down there, in my place, serving her.

I ate her pussy for hours. She came many times... her legs would squeeze around my head and her hips would buck uncontrollably. I would rub my nose against her clit, lick her clit, and stimulate it however I could. She had a larger clit, so it was easy even for me to find. Eventually we both fell asleep together exhausted. We didn't have any actual sex that night.

 

[Shidave]

Good story.

 

[NotEnufMan]

Part 2.2

Sorry, got interrupted on last post... here's more...

The next morning, we started by showering together. I was still nervous and had a hard time getting up for her. We moved back to the bedroom, she did everything she could to stimulate him. Having never even got head before, I got so excited that I came in her mouth. She prompty swallowed and smiled. We took a short break, then started over again. She finally got me rock hard tossed me on the bed, and slid her wet pussy around my cock,sitting down on me. About 5 seconds later, I came all in her pussy. She knew I wasn't lying about being a virgin. She cleaned up, then made me get down and eat her pussy all over again. After a few more hours, I was rock hard again. This time I lasted much longer. We fucked over and over again, until we were both in pain.

We decided to date and got together every vaction since. She and I talked a lot, online and offline, about kinky things to do. We played with toys, food (whipped cream and strawberries and chocolate) and tried all kinds of positions. We talked about doing a threesome. I couldn't believe we were even talking about it. She mentioned she had people that were willing down by her if I came to visit.

One day, when we were talking on the phone, she asked me "what do you think about open relationships?" I asked her why she was asking. She said that "a friend of hers" thought that a couple willing to have a 3 some really has an open relationship and should be able to see other people - and wondered if I agreed with that. I thought about it for a second - I thought about her with another man and immediately got turned on - I started to realize how much I enjoyed this thought. I wanted to say sure. But, I wasn't ready to accept that yet, and I thought it might be a test - open meant I could sleep with anyone too, and I didn't want anyone else... and she might dump me if she thought I meant I wanted to... so I said "no." She said (nervously) "yeah, that's what I thought too... what was he thinking?!" In retrospect, I now realize she was asking for permission to cheat - and I would've, and should've said yes had I known this.

After that conversation, she started talking about a friend of hers, R. They had a past relationship and were now friends. She also mentioned a couple other guys (I don't remember their names) she had classes with and shared secrets with. I started to get suspicious - but, as before, the thought of her cheating turned me on. I jacked off almost every night thinking of her and R., who I had seen a picture of. I was torn, pissed of at her sometimes because I KNEW she wasn't being honest, but turned on because I KNEW that pussy was being fucked by another guy.

Her spring break was long before mine, so I picked her up to bring her up for the whole two weeks. She stayed at my apartment while I went to classes. We fucked almost all the rest of the time, trying different kinky things, including some assplay (but not anal sex... she told me she wouldn't do that) Towards the end of the second week, I was fucking her doggy style and smacking her ass. Her cheeks were spread open in front of me, and her asshole puckered at me-then white, creamy cum started leaking out of her ass! I stared at it, fighting back an incredible urge I was having... I wanted to lick it out! My brain racing between being pissed off and turned on, I grabbed her hips and started fucking the hell out of her. I had mostly been gentle to this point, but now was being quite rough. All of my energy-angry and sexual-seemed to be concentrated in my penis. I came hard into her pussy and slapped her on the ass so hard it left a red handprint. She screamed so loud my roomates(and probably neighbors) surely heard her. As I got up from behind her she said that was great and asked what got into me. I said "I don't know" and left it at that.

The last couple days we experimented with being rough and spankings. Both our asses we red by the time I was driving her back. My brain was confused, but I was enjoying it.

As soon as I got back, I called my roomates in and asked them who fucked my girlfriend? They both started to laugh, finally T. asked "you don't know?" and I said "No." He laughed again and said "sorry, she said you guys had an open relationship and you were fine with it..." I asked him the details of what happened.

 

[NotEnufMan]

Part 2.3

I was at class, and J was watching TV with T and his girlfriend A. They were talking and got talking about their sex life. J then casually asked if they'd be interested in a four way with me and J. They were a bit shocked, but then A. said she couldn't do anything with another guy. J smiled and asked if they'd fool around with her. They asked if I'd be OK with that and she said "sure, we have an open relationship- i'll tell him later." They went into my room. J&A sat on my bed, and started by making out. It quickly got hot and heavy, they were pulling eachother's clothes off. T stripped, sat in my chair and jacked off watching them. J then crawled over to T and start licking and sucking on his cock. A. got behind J and started eating her pussy. T had to stop or he would've ended early. The girls (J & A) went into my closet and grabbed some toys to play with eachother. They started with my small purple vibrators, moved up to my 8" flesh dildo. J asked if they were into anal. They said yes and she took out my graduated anal beads and butt plugs. J. played with A's ass, pulling the beads in and out. T used my butt plugs on J, moving up to larger and larger ones. Eventually he moved up behind her, pulled out the last butt plug, and started fucking her up the ass. At the same time j. ate out A's pussy while playing with her ass with the beads. T was cumming in her ass when they heard my car pull up - and she kicked them out of the room.

After he told me, I congratulated him and said I don't blame him, I would've done the same. I went back to my room and jerked off thinking about it. Once again, I was torn. I was pissed at her dishonesty, but the thought of her with them turned me on so much, and I couldn't get the image out of my head. I was also pissed 'cause she told me she didn't do anal and wouldn't let me fuck her ass.

I called her a couple days later to confront her. I eventually got her to admit to it. As I continued to ask her questions, I got out of her that not only was she regularly cheating on me with R, but also another guy, C. I just couldn't handle it, and I broke up with her.

We didn't talk for a little while, but eventually warmed up again. She wanted to continue to be friends - so I said yeah, sure. During this time, she continued to send me pics in emails. Her playing with herself, just naked, some "artsy". In a couple of pictures there was a mirror and I could see R holding the camera. I also did some searches for her nick, and found some pictures of her and C together. It was driving me nuts... I still wanted her.

We started talking about a dance we were going to go to by her. She said she still wanted to go with me. I agreed. I went down and got to see her dorm, and meet some friends. R came by, and I got dumped off on her friends. After a few hours, she brought me back to her dorm. We sat down on her bed and she immediately started making out with me. She laid me back, smiled, took off my clothes and hers. She stratled me, lowered herself down on my cock... and I felt it... his cum was still in her pussy and I could feel it running down my cock. She squeezed around me and even more oozed out. Neither of us said anything about it, I grabbed her hips and fucked her hard as she rode me. It wasn't long before I came. As I came into her and felt my cum and R's cum both pour down my cock and on my balls, she leaned over me and whispered in my ear "that could've been a threesome if you hadn't broke up with me"

The next day we went to the dance. The day after I headed back. We talked less and less after that. I got mad as I realized I didn't matter to her anymore. To hell with the cheating, I just wanted to matter. As I realized this, I also realized I only had myself to blame. If I had just been honest about wanting an open relationship, maybe she would've been honest and I could've enjoyed it more.

 

[NotEnufMan]

Part 3.1

Sorry, it's been a long time. My wife and I just had our forth child. I'll talk about her in part 4. Here's the next part...

In the meantime, I had become a net *****. Visiting all kinds of chatrooms, I had two groups of people I chatted to, people I "cybered" with and people that I just chatted with. I was indiscriminate. I found that "real" women were hard to come by, so I cybered with fake ones, and even men who weren't even pretending. I started getting turned on by almost everything. I started regularly chatting with "Bi" in my name.

One day, I was chatting with "S." one of my "regular" chatters. Prior to this day, we hadn't touched the topic of sex, it was just normal chat - and I was pretty sure she was real. Suddenly, though, that's all she wanted to chat about. Me being bi and the fact that that turned her on. She'd always wanted to see two guys together. We swapped some hot stories, then she started asking to see me on cam. I asked to see hers, she said she had a came but couldn't get it working. I thought... oh... i've heard this one before. I guess she isn't a real woman after all. But, desperate and horny, I caved and went on cam for her anyway. She was very demanding of me. Asking me to go into all kinds of poses. She loved to see my ass and asked me to spread it open. She asked if I had toys and I said yes. She started watching me stick vibrators in my ass... loved to watch me set one down on my chair and ride it. She'd call me a dirty faggot and asked if I liked it, and I'd say yes. She sent me some pictures of her - normal ones, though a couple were in sexy poses. She again was the body type I like - big tits, big bubble butt, just a little thick in the middle. She had olive colored skin and brown eyes. The pics didn't make it more believable, I just figured they were ripped off from somewhere.

We had been talking about meeting. She lived a very long way away from me, but near one of my friends. I figured it was just idle chatter. Then, one break, we got serious. We set plans to meet - a restaurant close to where she lived. I packed up and started driving that weekend. I was nervous as hell the whole way - more so than previous meetings with people. The whole way down I was thinking to myself "you're crazy, you haven't even seen this person for real... you could be meeting a guy!"

I got to the restaurant, and there she was - real as life, and she brought a friend, A. with her. I figured she was being smart, she had backup in case I was a creep. We had some lunch and talked for a while. They were both goofy and fun to be with. We drove to a hotel nearby so I could check in - I was staying the whole weekend. I got into my room and put down my stuff, I turned on the TV, she and her friend sat down in chairs and I laid down on the bed. We talked a bit, then she layed down in the bed next to me, and pulled a blanket over us. I smiled. As we kept talking, she grabbed my hand under the blanket and guided it up her leg, and under her skirt. I quickly noticed that she wasn't wearing any underwear, as my fingers brushed against her wet pussy lips. She quickly spread her legs and guided my fingers inside her. She was giggling as a fingered her... her friend 3 feet away. She asked what we were doing, we just laughed. I fingered S. for a while. She reached down and unzipped my pants, pulled out my already hard cock and started stroking. Then, she pulled my pants and boxers down all the way, got on top of me, and slid her wet, dripping pussy down around my cock and began to ride. As I laid in disbelief that her friend was still sitting next to us, her friend yelled at her and said she had to talk to her outside. Her friend said "you just me him, he could give you some disease." She told her back "he's only been with two women, and he's clean" - "how do you know that for sure?" "well, it's too late now, so just let me have fun with him" she sighed and they came back in. I was now limp. That jarred me a lot. She did her best to try to get it back up, but it didn't work. She smiled at me and said "well, you don't need to be hard for some of the stuff we talked about" she then started digging through my bag and pulled out my mini metal dildo. She instructed me to lay down on the ground with my legs up in the air, spread, leaning against the bed.

I did, her soft hands slid against the inside of my legs, one with dildo in hand, brushing against me. She pushed the head of the dildo to my asshole, rubbed it around on the hole. She teased it and made me moan loud. Then suddenly, she just slid it in - i let out a really loud moan as she slowly slid it in and out. I had put dildos and vibs in me on cam for her, but this was the first time anyone else was putting one in me. Something about her touch and the softness of her hands made it feel really good. She was stroking my cock as she fucked me, and I came instantly, all over my own face. She laughed and told me "clean it up" as she kept fucking my ass. I was barely done eating my first cum, when I came again. They both laughed and she pulled the dildo out. "Need to save some for later" she said. I licked the rest off my face and we got dressed and headed out.

We went to a store, and they headed straight for women's lingerie. They were laughing and giggling as they looked at different bras and panties. They picked out a set and ran over to me, put them in front of me, and started snapping pictures. Everyone was looking. I was turning red. I wanted to run. They told me all their boyfriends had to go through this initiation. They grabbed me and brought me back to the changing rooms. They took off my clothes and put the lingerie on me, then paraded me in front of the whole store while snapping more pictures. I didn't know how they were getting away with it, turned out their friend N worked there and was letting them do it. I had never been so humiliated. After a little bit, they took me back and let me put my clothes back on. They sent pictures to their friends with their cell phones, laughing at me as we walked back to the car. As we got in the car, S said "don't worry, I'll make it worth it"

We were heading to A's house to drop her off. As I drove down the road, S reached over, started unzipping my pants, reached in and pulled out my cock. She was surprised when it was already rock hard. "You must've liked that, then, huh?" She smiled, leaned down and started sucking me off as I drove down the road, A watching from the back seat. It was only a few miles before I came again. We dropped A off and went back to S's house.

 

[NotEnufMan]

Part 3.2

The next day she asked "Did you bring the toy I asked for?" Yes... I said meekly. I was still hurting from cumming 3 times the day before and couldn't believe she was going for more. "Good, bring it out". I got the 8" realistic dildo out of the car. I reminded her that I was never able to get it in my ass on cam for her. She said "just get it, then get on your hands and knees." I got it out of my car, brought it to her, stripped naked, and got on my hands and knees in front of her. She strapped on the dildo, got behind me, spread my cheeks, spit on my asshole, rubbed it in with her finger, then pressed the dildo against my hole. It felt good at first. The tip went into my asshole, and she went slow, spreading my asshole little by little. I was moaning as groaning as she slid it in. She pushed harder and popped the head into my asshole. I screamed out in pain. She slapped my ass and said "just take it pussy" and pushed in harder. I felt my asshole rip and screamed louder and she put her hand over my mouth and continued to push it all in. It was now burning as she slid it in and out of my ass. I started cumming despite the pain, and she grabbed me by the hair, made me crawl back, keeping the dildo in, and shoved my head in it, making me clean it off the floor. After pounding my ass a little more, she took off her strap, leaving the dildo in my ass, and told me to lay on my back. With that, she sat on my face backwards. Her pussy was flowing with cum from making me scream. She slid the dildo in and out with her hands and i was now past the pain and starting to enjoy it. She slid her ass onto my face and made me lick it out, then went back to her pussy and came all over my face. We hung out with her friends the rest of the day and she continually embarrassed me by telling them everything we did.

The next day, I left to go home. She kept the dildo. I made a few more trips down. We did a lot of the same. She did more of making me lick out her asshole, riding my face, and fucking my ass, sometimes right in front of my face.

One day we were talking on the phone and she was crying. She told me she kissed this guy she knew, R, and felt really bad about it. I told her I wasn't the jealous type and not to worry about it. I didn't want to tell her I was actually turned on a little. I masturbated many nights thinking of her with another man.

Next time I came down, we were in my car. I thought it was odd that A went in the front seat and S went in the back. They said they had to pick their friend R up and bring him home. We went to the shopping center and he hopped into the back seat. They didn't mention he lived half way across the state. As we drove back, I started noticing them in the rear view mirror. She started rubbing on his body. A was talking to me, apparently trying to distract me. S's hand went down to his crotch, and I heard her unzip him. She pulled out his cock, which was massive. I'm not sure exactly how big, but definitely bigger than mine. I would guess about 9 inches. She then leaned down and opened up and started sucking his cock in my back seat. I swerved a bit, A told me to keep my eyes on the road. What proceeded is probably one of the longest blow jobs i've ever heard. She was moaning into his cock, he tossed his head back and moaned many times. Nobody really said anything. He started fucking her face, thrusting his hips into her. We got to his house, and sat there for a few minutes as she kept sucking until he came all in her mouth. After that, he just zipped up, and got out of the car. A directed me to a back road. I parked along side a corn field, then S reached around me, pulled me to the side and kissed me deep on the lips, spitting his load slowly into my mouth and swirling it around with her tongue. She then grabbed my crotch and said... "I have a confession, I didn't just kiss him, I fucked him, and it was good" She put on a cute pouty face and said "you're not mad, are you?"

 

[NotEnufMan]

Part 3.3

I just said "you can do anything you want when I'm not here". I didn't want to admit that it actually turned me on. "Good" she said and she reached down, unzipped my pants and pulled out my cock. She was a little surprised that it was already hard. She crawled between the front seats and sat on my lap. Rubbing her bare pussy on my cock. I could smell that familiar smell on her breath... and, in her pussy... that smell of cock. She slid that pussy down on me, started kissing me, and I just kept thinking about R's huge cock being in all her holes. There we were in my car, A in the passenger seat watching, she just got done sucking off another guy. I came inside her so quick it wasn't funny. She laughed. She pulled the lever on my seat, setting the head rest back all the way, crawled up my body and rubbed her pussy in my face. I could smell my cum mixed with the scent of his cock and old cum. I don't know when he fucked her, it was probably earlier that day. She rubbed her cum filled pussy all over my face until I licked it all up. Then she hopped in the back seat and asked me to take her home.

We only did oral the rest of that trip. I ate our her pussy and ass and made her cum many times. My dick hard thinking about her other bf being there first.

We chatted online some more after I went back home. She did some cam shows for me, including her sucking his cock and getting fucked by him. She was driving me nuts. I was eagerly anticipating the next trip down.

When I finally got down there again, she brought me into her room and said she had a surprise. I followed her in, and she brought out the bra and panties she and her friends made me wear on the first trip. "Put them on" she said. I did as she asked. "Wait here" I waited in her room on her bed for quite a while. I heard the door open, R coming in, the two of them making out, and finally fucking on the couch in the living room. They came in the room, naked, and sat down on her bed. She told me to get on my hands and knees. I got down on my hands and knees in front of her, could see his fresh cum dripping from her pussy. She grabbed my head and pulled it up to look at her. "In front of HIM" she said. I crawled over in front of him. "Suck him off" I looked at her and said "uh, i've never sucked a guy off before." She went to her computer and brought up and old chat we had. "you said here you did." I told her i lied 'cause she said bi guys turn her on. "Well, now you have to own up to it." I stuck out my tongue and slowly licked his balls and shaft. I tasted her pussy on it and began to lick hungrily. "That's it, little faggot" she said, now take it in. I opened my mouth and slid my lips around the head of his cock and started sucking. She was taking pics and sending them to her friends with her phone the whole time. I slowly slid my lips down his shaft as he moaned loud. I got about 6 inches in pretty easily, then it hit the back of my throat and gagged me. At that moment he came. I started to slide my lips off and she stopped me "you're not done yet, bitch, I want to see you deep throat him." With that, she shoved my head into his cock. I was surprised when my throat opened up to take it in. I gagged really hard when his head first penetrated into my throat, but then it slid in and out easy. He started fucking my face, I felt his balls slapping against my chin. He came again down my throat then pulled his cock out. "you're a good cocksucker" he said. "I never came twice from a guy before." S replied "I think you HAVE sucked cock before, faggot. were you lying then or now? Nevermind..." they went back in the other room and fucked again.

I never touched her body that whole trip. On the last day, just before I was going back home, she said we had to talk. Basically, she said that I was a little faggot cunt bitch and couldn't be her bf and that she was dumping me for R cause he had a bigger dick and got hard without thinking about men. I had a weird mix of emotions. I was crushed, but still turned on a little and I didn't get why.

When I got home, I opened up an email from her. It said "just so you understand... you're not my bf anymore, but YOU ARE STILL MY BITCH."

We chatted online quite a bit. She sent me pics of her bfs cock and of them sucking and fucking. There were a few cam sessions to. She'd do a lot of what she used to, asking me to use various dildos and toys on my ass. She was a bit meaner with the faggot comments though.

After a few weeks, she started asking to see me suck cock on cam for her. I found some random guys of the net, and brought them over and sucked them for her. She usually had me dress in the bra and panties she bought me. She was sometimes alone, sometimes A was with her, sometimes R was with her. They'd watch and laugh as I took all these cocks in. One day, I brought in a new guy, B. His cock was a good 10.5". It was the biggest I'd ever seen. She ood and awwed at it. I had a hard time sucking it all in. I gagged really hard, so loud they heard it through the microphone. I almost threw up, but I sucked in in and kept going until i felt his balls on my chin. He came in my mouth twice. He started fucking my face, I kept gagging as it slid out and in over and over again, then he pulled it out and came all over my face. I heard S moan loud as she came on her chair watching it and masturbating. It was just her that day. He left the room for a minute. She told me she really liked him, and she only wanted me to be with him from now on. She told me to ask him to be my bf. I argued with her a bit, saying I didn't do that, but she just came back with me being a pussy faggot and doing what she says and getting a fag boyfriend.

I left the room to ask him to be my bf. He was excited, said he never had a better lover. He hugged me and kissed me deep on the lips, tongue sliding all over. He wanted me to prove it wasn't just for her by sucking him off again without the cam this time. I went back to tell her what he said. She said, turn the computer off and go suck your bf, faggot.

She changed boyfriends a couple times, while I kept this one. She told me stories of things they've done. They were mostly dom to her, which was the kind of man she needed, she said. I jerked off my cock many times thinking about her and those other men. I sucked off my bf on and off cam many times. He had been pressuring me to let him fuck my ass. I was scared because I never had anything that big in my ass before. The two of them ganged up on me one day while on cam. I found myself taking my panties off and sitting on his lap. I lowered myself down on his massive cock. The head pushed against my whole and started pushing in. He got about half of his head in when my cock just started going crazy and came all over his chest. Thinking that might be a ticket out, I started to get up. He grabbed my shoulders and said "I don't think so, you're not getting up until you take him." She laughed and said "that's it, fuck his faggot asshole good." He pushed his dick up into my asshole, spreading it open. His head popped in rather easily. He had a weird little head though where his shaft was much wider than the head... and as he pushed his cock deeper into me, it stretched me like never before. As he shoved it in inch by inch, he tore my asshole and I screamed out loud. S laughed at me over the cam and told him to keep going, ram the whole thing into my faggot ass. As he shoves it in farther, I start to push past the pain. When his cock got about 8 inches in, I came again. I screamed in in pain as he shoved the rest in. He then continued to pound my ass by bouncing me off his knee. Soon I felt his hot load shooting into my ass. I got off of his cock and S asked me to bend over to see the cum dripping out of my ass. She said "good job, faggot" then logged off.

S changed boyfriends a couple times. She would make sure to share all the details of what they did together, making sure to make me jealous and watching me and B on cam and directing me in how to please him. When she started dating G, she got online with me less and less. Eventually, she told me she wasn't going to watch me on cam anymore, things with G were getting serious and she couldn't keep doing this.

I started to wonder if I was gay, as I had enjoyed sucking and fucking B so much. I kept dating B, ad he kept coming over to get his cock sucked and to fuck me for a while. He said I was the best fuck he'd ever had. It just didn't feel the same, though - I wasn't enjoying it anymore. We broke up and I moved on.