21 year olds journey to becoming a cuckold

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ae86

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I've been a member for a long time now without posting, and I finally decided to share my own true cuck story. Ive been reading yalls stories and I really enjoy all of them, so I feel like I should share mine now. I'm 21 now, but had my first cuck experience back in H.S. a few years ago. Its definitely one of the hottest experiences of my life and has inspired me since, so I will try my best to describe it well for you all.

Back during my Junior year of H.S., my girlfriend of the same age and I had been dating for nearly 2 years and had tried everything sexually. We had incredible sexual appetites and would fool around as often as we could even though it was risky with our parents around at our homes. Over time we got kinkier and kinkier in our play, and began to tell eachother sex stories during sex, through which it became evident she was really turned on by the idea of a threesome.

I should describe her, she was a 5'9 blonde with long legs and B cup breasts, beautiful all over. She loved giving oral and practicing it often, and loved to swallow (no lies, one day she gave me 5 BJ's swallowing each time!:D).

Anyhow, during this progression in our relationship our mutual best friend was going through a bad break up with his girlfriend of 3 years and was feeling a bit sexually frustrated. He always had a funny sense of humor and one day jokingly asked if she could relieve him of his "blue balls". She laughed this off and told me about it and nothing was said of it again till we were having another story session and I asked how she would feel about it. She became super wet at the idea of sucking another guy's cock (I was her first), and so I told her she could if she wanted. Later that evening she said she would give him a BJ and it would be a gift from the two of us for his birthday. They later set up a time for this to occur, and it would happen at my house the next weekend.

During that week we discussed the plans and I asked if I could be there while they fooled around to feel more comfortable. She said maybe and didn't speak much about it. I would later find out she had been so excited that she asked him to email a picture of his cock and measurements. On the day of, she came over and I tried to get her to fool around with me but she said no and wanted to keep her mouth and pussy "clean" for him. I felt strangely turned on by this and waited, assuming I would get my action later. When my friend came over we all sat in my room somewhat awkwardly and he asked if it was OK, and I said yeah sure. Then my girlfriend talked to me privately and said that he would only do it if I went into the next room during it. I reluctantly agreed, and went into my bathroom that is connected to my room and locked the door.

I didn't hear much except for her belt being unbuckeled and noises of zippers. From her account of the story, she sat him in my chair and took his cock out and hungrily licked his cock and balls all over. She said he taught her a move where she would twirl her mouth and hands over the shaft going up and down, and after doing that for a few minutes she took her top off and let him feel her nice soft tits. Around this time he came in her mouth and she swallowed his cum. She was so horny after this that she got into the chair and had him lick and finger her pussy, and she told me he fit three fingers in and hit her G-spot hard. Realizing the time passed, she put her skirt and shirt back on and he got his pants on and they let me back in. All the while I was going through all sorts of feelings, being jealous, regretting it, and being a whole lot turned on. When she opened the door she gave me a huge hug and kissed me, then she laughed remembering that she had cum taste of another man in her mouth when she kissed me. My friend gave me a handshake and we ended up watching a movie together. During the movie I tried to put her hand by my cock quietly, but she loudly stated "Im not gonna jerk you off" which was incredibly embarrassing.

We ended up going out for another year before breaking up before going off to college. I dont know how interested in cuckold fantasies I was before this experience, but afterwards I have always been turned on by the idea of my girl loving me but giving herself sexually to another whilst denying me.

My current girlfriend and fiance is 20 years old, even hotter, yet she is not as into the wild fantasies as I am. We have had sex many times, but she prefers vibrators on her clit because she complains that during intercourse my penis hits her cervix as it is as she puts it " too long" (only about 8 inches) and she wishes that it was closer to 6 inches. She did agree to be my keyholder for my chastity device, and keeps me locked up all week every week untill the weekend. Lately things have been looking up, as she has denied me release and said that she didn't want to play with my cock as it makes an "icky mess", yet she makes me use a vibrator on her and laughs at my predicament. When she has been letting me out she tells me stories to jerk to, and often they are of us being married and her locking my cock up for good and her sleeping with other men (I usually ask for these). As we are young and in college, we dont have intercourse for fear of pregnancy, so I suprised her by buying a small strap on for me to use on her. She loved it! I also found that she loves being fucked hard with the strap on from behind when nothing too long is hitting her cervix. She has joked recently that when we get married she might just have me use this all the time on her except when making children. Last weekend when she released me her story came without suggestion at all from me, and was about her locking me up and taking a lover with a "slim shorter" cock who can take her hard without hurting her, and then having me lick her clean afterwards (she came up with this one on her own and has no idea about the cuck scene at all!!). She said afterwards that she would never cheat on me, but her pussy was definitely wet. So maybe someday a nice stud with a slim 6 inch cock will come and fuck her hard the way she likes it, but either way I think Im living the dream now as it is being cucked by the strap on and vibrators essentially :D.
 
wow hot story....i've always wondered what it would be like to be in chastity. also, having sex with a woman using a strapon....that must have been incredible....keep us posted
 
An interesting - and frankly more realistic - couterpoint to the usual complaint about having to find someone bigger.
 
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Hm... you might want to consider "giving in" after a suitable show of coyness....

Ae86,

ae86 said:
My current girlfriend and fiance is 20 years old, even hotter, yet she is not as into the wild fantasies as I am.

Actually, I'd say she's doing well in that regard.

ae86 said:
We have had sex many times, but she prefers vibrators on her clit because she complains that during intercourse my penis hits her cervix as it is, as she puts it, " too long" (only about 8 inches) and she wishes that it was closer to 6 inches.

Eight inches is, in fact, quite long.

ae86 said:
She did agree to be my keyholder for my chastity device, and keeps me locked up all week every week untill the weekend.

Good for her. She has the right idea.

ae86 said:
Lately things have been looking up, as she has denied me release and said that she didn't want to play with my cock as it makes an "icky mess", yet she makes me use a vibrator on her and laughs at my predicament.

Excellent! She's showing very good skill at manipulating you sexually.

ae86 said:
When she has been letting me out she tells me stories to jerk to, and often they are of us being married....

Sounds like she has plans for you....

ae86 said:
....and her locking my cock up for good and her sleeping with other men (I usually ask for these).

....and she knows what she wants, and she knows how to let you know in ways that feed into your fantasies, such that you are likely to give her what she wants, because it turns you on....

ae86 said:
As we are young and in college, we dont have intercourse for fear of pregnancy, so I suprised her by buying a small strap on for me to use on her. She loved it! I also found that she loves being fucked hard with the strap on from behind when nothing too long is hitting her cervix.

Also very good! It sounds like you're imaginative and inventive. Maybe you should consider the possibility of asking her (nicely) to use the strapon on you, while she has you locked up in your chastity device...—?

ae86 said:
She has joked recently that when we get married....

Oh, oh. There's that word again, indicating she's moving you forward.

ae86 said:
....she might just have me use this all the time on her except when making children.

Well, that would certainly enable her to select a suitably-sized strapon dildo for you to use — assuming you could fit your cock inside of it. Alternatively, it would allow for the possibility of her requiring you to wear the strapon while continuing to wear your chastity device underneath it, thus freeing her from the unpleasant need to remove your chastity device.

ae86 said:
Last weekend when she released me, her story came without suggestion at all from me, and was about her locking me up and taking a lover with a "slim shorter" cock who can take her hard without hurting her, and then having me lick her clean afterwards (she came up with this one on her own and has no idea about the cuck scene at all!!).

Ah, sounds like she's getting it.... as for the idea of her having "no idea of the cuck scene," how do you know? A corollary of unlimited information being available to you via the Internet is, the same information is also available to her. Maybe, for example, she reads and follows this site....

ae86 said:
She said afterwards that she would never cheat on me....

No, no, of course not....

ae86 said:
....but her pussy was definitely wet.

Hm... I think your woman friend is both sexual and sexually imaginative, and shows high potential. If she continues to move you toward marriage, you might want to consider not resisting too strenuously. You'll need to be coy, of course. I mean, a guy has to maintain appearances. But, it sounds like "giving in" after a suitable show of coy resistance could definitely be in your long-term interest, as well as hers.

—Custer
 
My first cuckold experience occurred when my high school girlfriend (Jane) and I were just 18. It was the summer following graduation and, with my full encouragement, she seduced my best friend right in front of me.

This first incident was totally impromptu. I knew she really liked sex and she was a natural flirt, but we had never discussed involving anyone else in our sex play. She had dated another buddy of mine during high school and I knew he had fucked her. She knew that my dick got really hard when she would tell me about having sex with him.

I was unbelievably turned on as she seduced and fucked my buddy in front of me. I loved watching her suck his rock hard cock and then watching her spread her legs for him. She wrapped her arms and legs around him and let him fully enjoy fucking her. I almost came when he buried his cock in her and started filling her with cum.

Jane and I discussed the incident afterward and decided that we really enjoyed it. We started a list of guys we went to high school with who Jane thought it would be fun to fuck. She fucked everyone on our list, some of them in front of me and some alone. We were together for over 8 years, during which time she also fucked many other guys.

I have ben with my wife Kate for 20 years now and she never stopped dating other guys. I love being a cuckold.

Rob
robandkate@hotmail.com
 
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congrats to you Rob and Kate

Very hot story and I like that your current wife never stopped dating. My wife went from dating to not dating to dating to not dating. Im trying to gt her to start dating again.