How I became a cuckold back in the 90s before it was a thing. [humiliation] [virginity]
My Six Months as a High School Cuckold
I was head over heels for Jen, my innocent-looking Jehovahs Witness girlfriend. Long dark hair, big doe eyes with round glasses, petite with perky C-cup tits that strained against her Smashing Pumpkins t-shirt, and a plump, tight ass that drove me crazy.
For two years we dated and took it so slow, 6!months for a kiss, second base after a year. She was saving herself for marriage because of her religion and her extremely strict upbringing. Then she started talking about how much her “bitch mom” was pissing her off. Then her and I started getting into more trouble in the back of my SUV.
I worshipped her body in the back of my SUV at lunch and during spares we had together. I’d spend hours on my knees with my face buried between her smooth thighs, licking and sucking her tight little pussy until she came over and over again, soaking my face with her sweet juices. She loved it. She’d moan my name, grind against my tongue, and shake through multiple orgasms. But she never touched me and we always kept my pants on because she was terrified we would have sex and that was saved for marriage.
Then one day I had her so horny she surprised me out of the blue and decided she was ready to lose her virginity! I remember her devious words… “fuck it, fuck me… put your cock in me and fuck me!”
I was rock hard whenever I went down on her… when she sprung that on me I felt like I was going to pass out with excitement. I fumbled at my pants taking them off so excited and went to rub myself on her wet slit and the second the head of my cock pressed against her slick virgin entrance… I went completely soft. I was enraged at myself trying everything but I was just way too nervous and excited.
We tried three more times in subsequent days. Every single attempt ended the same humiliating way: throbbing with need one second, limp and useless the next. The shame was soul-crushing and I could see the very real disappointment in her eyes. After that, we stopped trying penetration altogether… she stopped bringing it up and we just went back to me going down on her. My dick had proven it couldn’t do what a real man’s cock could.
A few months later she was acting really weird. Very pulled away and she wouldn’t look at me. I kept pursuing her asking what was wrong and she finally broke down crying and confessed. I remember like it was yesterday, we were in the library during a study period.
She had met Jake at a church family camp. He was from another town 20 minutes away and she said he instantly had eyes on her when they met. She went on to tell me a graphic intense story of how they fucked the same weekend they met. In a dimly lit janitor’s closet he had pushed her against the wall, yanked her panties down, fingered her dripping wet pussy, and taken her virginity with one powerful thrust. She described how full he felt, how big he was and how forcefully he fucked her. I was devastated and weeping but told her I deserved all the details. I ran out crying from the hurt and just drove home. I stayed in my room all night crying and felt like puking. It was so painful recounting all the details in my head. What she was wearing, how forceful he was, how she said she felt horrible but it felt so good. I broke inside that night but in the morning woke super horny and hard. I stroked it thinking about all the details and how much of a pussy I was and came instantly… but I stayed hard… and proceeded to go two more times before I was raw and done. I still felt sick but now I had something else, a new intense feeling.
I went to school, found her, and convinced her that I forgave her and loved her and wanted to make it work. I told her what happened and that I loved the details and that it made me so close to her. She was confused but seemed to just shrug and say “ok…”
We stayed together for another six humiliating, intensely erotic months.
During those months, my role became crystal clear: I was her pussy-eating boyfriend. Almost every day we’d park somewhere secluded. I’d bury my face between her legs while she casually told me all the filthy details of what Jake had done to her. The more she talked, the wetter she got.
Then she started asking if she should try and hook up with him again and I was so hooked I said “absolutely!” And she was so horny and laughed and wanted that too. She would talk about how she wanted his big cock and what he was going to do to her. She would tease me lovingly about how I couldn’t get it up because I wasn’t manly enough to take her. I started cumming in my pants and she would laugh and say “gross” 😅
One afternoon I had her skirt bunched around her waist, her panties on the floor of the SUV, and my tongue buried deep inside her when she started stroking my hair.
“Mmm… I have a surprise for you… I saw Jake again on Sunday… turns out he doesn’t mind driving 20 minutes to come to my church…. After the service we went to his truck…” I was on fire and so excited! I told her to tell me all about it while still licking her beautiful pussy. “Jake made me suck his cock…” she purred seeing how I would react as she never even touched mine. “His cock is so much harder and thicker than yours, baby. We jumped into his truck laughing and he just grabbed my head and started kissing me deep ramming his tongue down my throat. I was so hot thinking my butch mom was inside the church still and I was in the parking lot being a slut… he pulled down his pants and he was big and hard and he just told me to suck it… so I did. I’ve never done that but he taught me. I could barely get my lips around the head. He held my hair and slowly fucked my mouth, pushing deeper until I was gagging and drooling all over him. He knows I have a boyfriend but he didn’t care at all… When he came he held my head down and shot straight down my throat. I gagged and he laughed and told me to swallow it like a good girl and I did. It tasted so warm and thick… nothing like I expected. I’m not sure I liked it and I absolutely will never do that with you…”
I moaned pathetically into her soaked pussy, licking faster, my dick leaking uselessly in my pants. She came hard, grinding against my face while telling me how much she loved that experience with him. How she loved how he just took what he wanted.
A couple weeks later she was especially wet and told me something else happened…. She asked me if I really loved her. I said I did. Then she asked if I would leave her if she fucked Jake again. I told her of course not, that I wanted that, and that I wanted all the details.
“Jake fucked me again last weekend… really hard and long this time. We drove out here where you and I always fool around, the lookout point, I told him I knew a good spot.” She said laughing.
“We got out and he laid me down on the grass right there.” She said pointing to a spot of grass that was tamped down. “He didn’t even ask he just pulled my skirt up, spit on his cock, and shoved it all the way inside me. God, he went so deep. He kept calling me his dirty little church whore while he pounded me. He fucked me for 20 minutes and we both had an orgasm while he was in me. He kissed me so hard. I really hope I don’t get pregnant… I was sore for days… but I kept thinking about how you can’t even get inside me at all and it made it so hot thinking about telling you all this while you licked my pussy.”
She laughed softly, then moaned as another orgasm built.
Over the next few months, she had more stories about Jake. The most intense was when she told me about the anal.
I had two fingers inside her dripping pussy and my tongue flicking her clit when she dropped it on me.
“Jake took my ass last night,” she breathed, voice husky. “It wasn’t… super fun the whole time. It hurt a lot at first. He got me on all fours As he likes to fuck me now… he spread my cheeks, and spit on my ass and started pushed that thick cock against my tight little hole. I told him to stop, that it was too big, but he just held my hips tighter and kept going. He’s so masculine, so dominant… he just took what he wanted and I felt so powerless to stop him you know? He pushed his way inside me inch by inch while I whimpered and gripped the blanket and cried. It burned and stung, but the way he grunted and called me his property… it turned me on so much. He fucked my ass harder until he came deep inside it. I didn’t cum, but I loved how badly he wanted it. How he didn’t care if it hurt me he just claimed me. It was kinda hot how I realized Jake had taken all of me.”
She was grinding hard against my face now, soaking me. I was shaking thinking about the love of my life being used like that. Such mixed emotions, jealousy rage, wishing I could have watched, lust… what a cocktail.
She went on… “Afterwards I felt so used… and so fucking owned. You could never do that to me, could you? You’re too soft. Too small. Too much of a pansy faggot” giggling she watched as I came again in my pants wriggling around from her words alone.
I whimpered as her words burned into me and again something like it snapped inside of me.
By the end of the six months, Jen had completely changed. She dressed sexier and had a nose ring, and barely even pretended to respect me anymore. I was just the eager tongue that cleaned her up and listened to every dirty detail.
The final day, we were in our usual spot. I was between her legs, desperately licking her well-fucked pussy when she suddenly pushed my head away.
“I’m done,” she said coldly, looking down at me with contempt. “This is pathetic. You’re never going to fuck me. You’re just a faggot with a tiny useless dick who gets hard listening to me get railed by a real man. I don’t even like Jake anymore. I’m just fucking him to play this stupid game of yours. I thought eventually you would take me… if I did enough or said enough, you would man up…” she was really angry getting dressed…
“Stay here and jerk your little dick if you want. We’re through.”
She grabbed her bag and walked away without another look back.
That breakup broke me… but it also awakened the cuckold in me forever. The memories of my sweet religious girlfriend turning into Jake’s eager slut… telling me every detail while I worshipped her with my tongue… it still makes me throb with humiliated arousal years later.
That was the beginning of my cuckold journey. I’m