first girlfriend and a cuckolding experience (a true story)

This is not a feel good story about cuckolding. This is an entirely true story and something that caused me a lot of emotional pain but years later it's still all I think about and secretly desire.

I met Kathy on an internet gaming site while I was going through a tough time at college. She lived on the other side of the country but I took the risk to fly out there as I longed for companionship and we seemed to have a really easy going relationship. And in real life it turned out to be a very pleasant. She was older than me but on the immature side. She was a gorgeous feminine plus size woman with a laid back southern demeanor and a voice of an angel. Are 1st night together she surprised me with a candle lit room and the romance was instant and we were in love.

My biggest worry like most young men was my penis size. At 4 1/2 inches long I felt a bit inadequate and Kathy being on the plus side made just about every position other than missionary very difficult. I could not touch bottom with her and could not even feel her cervix with my fingers. Doggy style was laughable as I could not go more than 30 seconds without slipping out and every time we tried it was the same situation and as discouraged and embarrassed as I was, it never seemed to be an issue with her. Now don’t get me wrong, she enjoyed sex with me. I have a strong endurance and I have a good girth but there was still something missing. Every time I slipped out during sex, which was frequent, she said “oopsie” in a childish voice which conveyed to me the idea that I was equipped with a boy size cock, but none the less a cock she loved very much.

There were little signs here and there that Kathy was a size queen. For starters she had a huge purple dildo in her night stand that dwarfed my size. She talked a great deal about how huge a friend of hers from online is and how they almost hooked up. She held up her arm and clenched a fist to represent his cock and said, "he's like this big," with her lips closed tightly together and almost squinting at the thought of such a masculine phallic symbol she represented me with. She followed that with, “you should see it” as if it was a sight for all to admire. Her telling me this was strange but I found the thought of her with a larger guy very erotic but I bit my tongue and I think she had a hunch she could talk this way in front of me without conflict, but rather it instilled intrigue on my part. Also to my dismay, a close internet friend of hers who knew of Kathy’s crush on him sent her a photo of him inserted inside his girlfriend with a lit candle stick planted mid shaft, I think only to point out to her just how long and stable his cock was. Her showing this to me had me concerned. One night while watching a short documentary on television with her about hung black male strippers … (now for those of you questioning this, it wasn’t a routine thing for us to watch these kinds of programs and this particular movie caught us both off guard) … she grabbed a hold of my hand to engage me in romance as she was totally turned on by watching these women gawk at these super hung studs that swung down to their knees. My hand started to sweat profusely in hers and I was in a sheer panic as to what might be going on in her head. I was turned on but embarrassed all at the same time at the thought of the comparison. Soon after I got into watching hung black men with white females on the internet and she found I secret porn stash and commented on how much it turned her on. Again I panicked and shied away from taking the conversation further.
One night I almost instinctively used her favorite purple toy on her measuring 8 ½ x 6, mostly out of curiosity. I saw her eyes go to the back of her head as I worked the toy down deep inside her, what seemed like miles away from anything I could accomplish. She immediately grinned, embarrassed that I had witnessed what I already suspected, which was that she thoroughly enjoyed larger men. So turned on I was at the pleasure this caused her and without second guessing I took my own turn. I could not feel a thing. It was a cavernous space previously plowed and still very much stretched and excited to accept what I could never give her. I knew If I couldn’t feel a thing, that she couldn’t feel a thing either. The silence and the empty look on her face spoke volumes. I went through the motions and eventually her pussy came down to fit my size, which was a relief.
It was the next day she started to play around with my soft penis, which must have been an inch at best. She closely examined me at first with a long stare and an odd pause, then slowly turning it side to side with two fingers. I watched in confusion. Her exact words which I can play back in my head, “you’re so little.” My heart sank immediately and she quickly corrected herself but almost in a ... like voice saying, “but then you get so big.” And later describing it to a friend of hers while ... and actually taking a ruler to show her my size to warrant the comment from the friend, “he’s short and stubby,” which Kathy responded with a nod and a smile.

Eventually though it came time for me to go back to college. With 2 years left and the fact that ill be on the opposite coast, she made it clear she was going to entertain the idea of having a lover on the side.

While back home and on that same gaming site we met … ( The back story of that site is that I was well known there as not only a competitive card player but with a huge ego to boot and I made a lot of enemies along the way ) … a friend of kathy’s named Kim was posting a link in the lobby of the site. Apparently Kathy had sent her friend Kim, who in fact despised me, a picture of me standing erect. This photo she took without my approval with her camera phone. It was the first time I had seen a photo of myself like that, and what I saw was a boyish cock. I quickly closed out the page. Blinding anger devoured me. My vision went black for about 5 seconds. The whole site was a buzz about this new revelation that what lurked behind my huge online ego was a fraction of a man. I was routinely known as “lil dick” on that site. A woman told me that even Korean men were larger. People would make jokes and ask me things like, "how's it hanging, no pun intended." No pun my ass.

Now of course I know this was a major exaggeration as I was not quite fully erect but still at such a young age I took all these comments to heart and its shaped the person I am today. Damaged yes, but with an insatiable appetite for the cuckolding lifestyle.

With persistent questioning I found out that Kathy meant this photo to get out there. She wanted to hurt me. She was very possessive of me and this was insurance for her that with a bruised ego I couldn’t entertain the idea of having a woman on the side. And to make matters worse she had already made plans to meet what was to become her frequent lover in Vegas. I knew very little of this new man in her life. What I did know is that was frequently posting about the number of orgasms he was giving her online, a number which quadrupled anything that occurred with us between the sheets (10 times..15 times…), again with the intent to bruise my ego. Through a mutual friend named Rachel I found out that she had slept with the same man years ago. She confirmed to me that this man was beautifully hung measuring 11 ½ inches and he had quite the following online. To add insult to injury, Kathy told me of the experience saying, “the best sex I ever had.”

…To be continued or not, you decide ; )

Please continue...

A lot of time went by where our communication was very minimal and the exact nature of our relationship was up in the air and was looking troubled to say the least. She commented on her devilish ways over a long distance phone conversation saying, “ I have never treated anyone as badly as I have treated you, and I don’t know why. “ I began to interrogate her , “what did I do to deserve this…and what is the nature of the relationship between her and her new lover” (which he was known to me as kaxx online and later as Frank)…, and lastly and more heavily weighted in my mind was, “do you think I am small.” Kathy always calm and collected under pressure, and as it turns out a woman always able to get what she wants, begins to address my concerns saying, “I love your penis”, followed by a long pause. I nervously pushed forward with my questing, “do I satisfy you as much as he does?” Kathy in revelation that I was prepared to hear the worst said, “ohh”… then taking then a brief moment to gather her thoughts,”Do you really want to know?” “yes I really want to know”, I stammered. Kathy, still seemingly relaxed stated, “I enjoyed are time together and with Frank It’s a different kind of sex, ya know?” Not ready to quit I asked, “well who is better Kathy?” She continues on now with an excitement in her voice and still completely at ease, “Well it’s definitely a whole different experience. It was a life awakening moment the first time I had him inside of him. It was everything I desired and more. He fills spaces inside of me I have never felt before”. I was having flash backs now of my sexual experience with Kathy racing through my mind and in a new light from what I previously remembered, like all the times she laid there motionless and an occasional bored look on her face. My ego deflated in total defeat I asked, “do you love him.” Her responding with yes ended the conversation and our relationship was now void of all emotion. For a while there was no me and Kathy. Are paths occasionally crossed online but no words were exchanged, until a year later a rumor had It that this man was married and was never going to leave his wife. She was the first to break the ice asking, “why haven’t you tried to contact me.” Now at this time I was in a real rut in my life and was disenchanted with my schooling. I missed my time with Kathy. Everything seemed so easy with her and I wanted my life back. As If nothing had changed, I told her I missed her and that I wanted her back but something had to change. “you’re right some things have to change”, Kathy interrupted me and then firm with her line of reasoning laid out the ground rules. “I want to be with you and be with and other men too.” I couldn’t believe my ears. It was obvious she knew she had me around her finger. She could have her cake and eat it to and I was not to going to have a word to say about it. Furthermore saying to me, “we will treat each other with love and respect and also you will respect my choice to be with a lover of my choosing.” Not ever imagining this was possible, and I’ll remind you this was before I knew what a cuckold was. Intrigued I asked, “you want an open relationship.” “no,” she replied, “I don’t want to see or hear about you being with anyone else.” This was unfathomable to me, beyond humiliation. I was being made to feel like the woman in the relationship. There was a joke she had with me that she wore the pants in the family. Not knowing then what I knew now was just how effeminate she saw me. It wasn’t just my cock it was my entire push over personality. And it was true, I liked to cuddle more than she did and I certainly lacked the confidence and ability to speak my mind so assertively as she did. She wanted more. She wanted a real man but still was undeniably in love with me still. Pointing it out to her how unfair this scenario was and how I was expecting an apology for what she did to me. She told me, “I’m sorry, very sorry for what I had done to you but that I can’t see are relationship progressing further without you honoring this one request.” I asked, “what about what’s fair, or do you just not care?” Kathy desperate to make her case now concluding, “listen baby, I love you but you know you’re cock is too small for me.” Confused, I asked “ what then did you love about my cock.” Kathy said, “ well I love you and everything about you and you make excellent use of what little you have but that doesn’t always equate to mind blowing sex. I’ve wanted this my whole life since as long as I can remember.” Frustrated that she was just wasting her breath on me she said, “you can either be with me or sulk like a whiny woman.” “Is that how you think of me”, I asked. Frustrated that her attempt to persuade me was not going anywhere she continued, “This is what I need to be happy and I need to know If you’re ok with that otherwise I am just going to hang up.” This cold tone of voice kept me distant still, but I paused for what seemed like forever, imagining in my mind just how much she enjoyed her time with Frank and what a vision it would be to see to see her with a man two or three times my size, and I said simply, “ok”… so unclear was my response she waited to see what I would say next. I started to tear up. “what is it,” she asked. I muttered, “what If you leave me for another man?” Realizing she may in fact achieve the impossible , have her cake and eat it to, her demeanor lightened up and like sunlight breaking through the clouds she said, “ I love you and want to be with you forever and always. No worries, ok?” We professed are love for one another.
So it was to be that we were going to embark on this journey of discovery about each other and what are relationship could endure. I flew out there a second time. I thought no other couple had ever managed before, but I trusted in my open mindedness and I was increasingly curious as to what it would be like to see Kathy with another man, and not just any man at that. Soon enough, I got to taste what it means to be a true cuckold for the first time. But would it last?
Should I conclude with the end of the story? ; )

Please finish this great story

Life went on actually fairly normally with us living together, except in the bedroom. I incorporated her toy much more frequently in our love play and it was clear that this was a rehearsal for the real thing. I would always take a turn inside her, but only after I finished her off with the toy and never before and strangely enough, although privately, I began to enjoy the humiliation aspect of it for the first time. She teased me with now with more exaggerated expressions of boredom, and yawning; and to the extreme of her reading a book, and even one time falling asleep on me. I ate her out much more than I ever used to and I was learning enjoy the submissive aspect of that. She was prepping me by desensitizing me and it was working. I eventually took the initiative to help find her a lover. I told her, “it’s time” and just like Christmas was around the corner, we excitedly made plans of how we were going to attract a man of immeasurable proportions. Kathy wasn’t one to talk of inches as that was more of a man thing but she made it clear to me that the bigger the better.
Finding a man to fit her needs was not an easy task. Sure there are a lot of well equipped men out there more than willing to please, but there is quite the difference between finding the typical large 7 incher from her previous lover. I was starting to question whether or not these sizes existed outside of porn. But we were lucky enough to stumble upon a website called lpsg, short for large penis support group. This was like a sanctuary for men with large cocks. Expecting a fair amount of women in these forums, I was surprised to find just a few women there which of course wasn’t the point but it had me questioning If Kathy’s desires were uncommon. I questioned Kathy of this and it was hotly debated. It was clear she is somewhat of an exception and a true size queen. But it was also clear from what she knew of talking to her girlfriends was that many have similar desires but it’s far from a focus of theirs like she has and that for many women after college and having children, a well endowed man may be nothing more than a distant memory for some of them, but often times a pleasurable one. She also explained that there are so many other qualities to a man that a woman looks for and penis size ranks low on the list for many. But more crucially to her argument was the idea that women just don’t settle for anything less than 5 inches, that anything more would be sufficient even for someone like her but since she’s going to have a lover she may as well fine the perfect size for her, among some other attributes she attributed to being sexy. She had just about everything she wanted with me except for that one thing and she wasn’t going to let it go, not after having had Frank, and definitely not since she felt she was in control of our relationship.
It wasn’t too long before Kathy, with her charming personality, captured the affections of an older gentleman named Tyler who lived nearby and frequented the lpsg chat room. Their relationship was that of a real couple, they laughed, they shared their personal pain and struggles, and when the too of them talked privately on the phone in her bedroom with the door locked I could hear whimpers from her. He knew of me but we did not engage in much conversation. His only focus was Kathy.
Now I have no idea if Kathy was seeing this man already without my knowledge but it was unlikely since she was never late from work and like clockwork she would be on the computer chatting away with what was inevitably was to become her new lover. It took about 6 months before she was comfortable with embarking on a sexual relationship with this new man. He was African American, 6ft 2, 250 pounds of muscle, and sporting a 9 inch erection and a whopping 6 3/4 inch circumference. He had a calm, cool , almost calculating personality, and a deep masculine voice. He put Kathy to ease and laid some of my concerns to rest. This was going to be purely sexual and nothing more. Now to my surprise, Kathy wanted to have her first encounter without me watching. I reassured her It was something I wanted to see and she had nothing to be embarrassed about and that I would only watch.

So the time came when the three of us were aquanted with each other. I won’t lie, there was some marijuana being passed around and a lot of giggles on kathy’s part. There was whispering between them and I wondered If it was about me and if that’s what they were laughing about or If they were whispering about how much they badly wanted each other. But there was a complete disregard for my feelings when Kathy pinched her fingers and a few inches apart and said to him, “he’s like this big,” followed by intense laugher between them and her falling into his arms. It was clear he had his eye on the prize and the way her eyes lit up when she looked at him further emasculated me. I got sick from the marijuana and went outside to take a breather. When I came back in I saw the two of them in an embrace sharing a slow passionate kiss, his hands cupping the back of her head. Like walking on egg shells I tip toed to be near them while they made out. This was shaping out to be something more than purely sexual, there were emotions involved between the two of them. Unable to stop this, I watched on, and very much sporting an erection of my own. I could see the outline of his cock in his pants, and it looked much bigger in person than from what I seen online. I became non-existent in the room as their eyes locked on and they undressed each other in a fit of passion, her down to her skimpy black lacey lingere and him with his shirt off and his rippling muscles on display. With her hands on his masculine arms she kissed him 1st on the lips and then made her way down his chest, slowly and in a very lovingly way made her way down to her knees while he stood before her. Unzipping his pants he sprung into action, his cock almost hitting her in the face, and she excitedly perked up as if very surprised, and said “oh my” and then giggled. But quickly it was serious again. She grabbed a hold of his cock gracefully with two hands, one at the other caressing him. She starred at the head of his penis a long time. She examined him just as she examined me before but this time with awe in her face.

While in the bedroom Kathy got on all fours on the bed, and I never seen her jump to missionary position so quickly before, because with me that position was impossible to manage. But he wanted to see her face the first time he entered her and so he grabbed hold of her and put her on her back. I was amazed out how he could man handle her as she was plus size and he lifted her around seemingly effortlessly, like he was going out of his way to impress me and give me a show and I’m sure to wow her. He gently teased her with just the tip of his penis, like the peak of mount everest, similar as I used to do with her but instead his tip was like my entire cock and his teasing was what was for me full thrusting. . I wondered if are entire sex life was like one big tease with my short stubby cock. Then he entered her completely and surprisingly fairly quickly she was consumed by his entire length of him, deep down beyond which my imagination allowed for and it was all in a matter of seconds. There was no discomfort on her part and in fact it was sheer pleasure that I witnessed on her face as he bottomed out and her saying, “awwwwoooohhhhhhhhhhhhhhhhhhhhhhhhh myyy GOD……you’re cock is so deep.” He swayed his body side to side, up and down forcefully now, and it was about 30 seconds before she orgasmed, unlike nothing I had ever seen before with us, first with a gasp, then she held her breath like she was about to explode, her face went red, her toes curled, her eyes shut , and the hair on the back of my neck standing up as I watched, she gasped and shuddered for about 10 seconds, her body trembling. Then it was absolute silence on her part, her head moving side to side and her face tightened as if in pain but instead, she squirted all over his cock, nothing I could have ever imagined Kathy doing nor did I knew was humanly possible. Now when Kathy orgasms her vagina clenches hard, and with me she pushed me out every time like a slippery bar of soap. He had too much length for her to push him out and the tight grip she had on him sent waves of pleasure over him, the two of them locked on in intense orgasmic pleasure, and he too shuddered and soon milky white cum came pouring out of her, much more than the dribble she was used to with me.
He then lay inside her embraced in each others arms, him caressing her hair, and her kissing him like she was in love and infatuated by his masculinity. His cock slowly poured out of her and for what seemed like forever, finally, his softer but still very long cock came out of her and made a thud noise on the bed. She laughed and quickly sighed. She was hungry for more of him and there was a long night ahead of us.
It amazed me how he could forcefully lift her up with his own cock and when she rode him, which we could never do as she had no distance to come up from, it was like she was being held up and supported entirely by his cock. I enjoyed especially while she was on top and she sank down on him slow at first but then forceful on her part to make sure he got all the way in, and he was without an inch to spare. They went from one position to the next with him not even having to remove his cock, amused we both were by this, we glanced at each other and she smiled at me. I moved in to caress her as he continued to plummet inside her. I started to kiss her feet, then her legs, and very sweetly her forehead and we shared a kiss. I ran my hand through her gorgeous blonde hair. With a distracted look on her face and annoyance, she grabbed my hand and almost pushed it away from her. Focused intently on him and only him, I was nothing more than a fly on the wall at this point. While completely absent minded of her lack of respect for me, their eyes locked and he very rhythmically plummeted deep down inside her. Her pussy hugged his huge girth and her cervix was pressed in towards his massiveness with each and every stroke. I couldn’t get over the sight of that rock hard black cock and the sharp contrast with her silky feminine pinkish lips. With her legs dangling and then soon gripping around his waist to pull him even deeper inside her, many orgasms followed and at some point I dozed off after having masturbated myself several times.
I was soon nudged by Tyler. He was nearly dressed at this point and she was laying with her legs sprawled out and awaiting my advances. Her pussy was wet and gaping open like it could take a football or a better analogy like she had just given birth. Not knowing what to do but still mesmerized I moved forward and examined her as she examined me before. As amazed at she was with how small I was I was in a similar awe to how full he made her and I could see deep inside her luscious vagina. She said, “put it in me baby boy.” Remembering are rehearsals from before I attempted to enter her but like a no net basketball shot I felt nothing but her dripping wetness. And it was followed by her oozing out this warm cum Tyler and previously deposited inside her. It was a very odd shivering experience, humiliating to the 10th degree, as I fucked what was his black mans seed inside her. She said in a matter of fact tone of voice said, “I can’t even feel you… are you enjoying your cream pie baby. Why don’t you lick it out of me.” Mortified though I was, I went through the motions.
The end result in my next post

Sadly I was too young and could not comprehend what took place. Fearing she was in love with Tyler, and maybe she was maybe she wasn’t, but I was too cowardly to find out and left the situation battered and bruised. I was left with feelings of inadequacy for a long time which actually killed my single life. I now know that Kathy and maybe a small fraction of women are a size queen to that degree and that I am more or less average in size, but what’s average when compared to these hung studs. My thoughts progressed into that of a cuckold. I have for a long time desired to find the cuckoldress of my dreams. I’ve tried telling women I was with about this fetish but they are generally disgusted or confused and as discouraged as I am sometimes, I know If there is a next time, I will be ready and willing.

very nice