Virginity Lost By Rape by Katie_Johnny

A literotic sexstories: Virginity Lost By Rape by Katie_Johnny ,
I was his first sissy, he was my first man. Our first time having sex was not planned
Virginity Lost By RapeI try to write in a generally fun tone, and to be honest, most of my experiences with guys have been fun. There have been some wild adventures, some nerve wracking adventures, and a whole lot of steamy sex, but my introduction to being a sissy for men wasn’t of my choosing. I’ll give a brief background of what led up to that night, then follow with the details.

As I’m typing this, I am realizing that this is the first time in my life that I have ever acknowledged out loud to anyone that I was actually raped, just like a defenseless girl. It’s sort of blowing my mind to confront the reality of the situation. If you’re reading this story, then I obviously made it through the recollection process and forged ahead, no matter how painful.

I’ve told a story about this guy, Brad, on here already. It’s called “Three Firsts In One Hazy Crystal Clear Night.” He was the first cock I ever sucked, and the first guy to catch me wearing panties. He was the only guy who knew about my sissy side for the first 30 years of my life. We would both hook up with girls as well, but after we had hooked up with each other, and if we were ever alone, we would hook up. He would bring me lingerie to wear, and I would gladly suck his cock until he exploded.

He was a sweet guy most of the time. In fact, this one night was the only time I ever saw him being aggressive towards me or anyone, and his aggression towards me was a culmination of being extremely horny and extremely wasted. Simply put, we loved each other beyond hooking up. We had been classmates from kindergarten all the way through college. He was the baby of his family, with 4 older sisters and 1 older brother, and wealthy, detached parents.

I can’t believe I am coming to grips with the fact that he raped me in real time, as I’m writing this story. Here’s what led to losing my virginity to him. After we had hooked up a few times, he wanted us to join another band together and tour the frat band circuit, making money and going all over the south. I wanted to join a band with him as well, because aside from the music and money, I genuinely enjoyed his company and I loved hooking up with him.

We played a show in New Orleans, at Tulane University, which was about an hour and half from our hometown. The show ended at 10:30pm, and the rest of the band took the gear and the van and went home. Brad’s older brother was out of town, and he lived in the French Quarter and owned a restaurant there as well, so he and I stayed in New Orleans for the night.

We went back to his brother’s place and showered up to hit the streets. I got out of the shower and Brad had laid out a brand new dark red Second Skin Satin bra and panty set. They still had the tags on them. Not gonna lie, it turned me on and made me feel special. I said nothing about them to him, didn’t thank him, and just put them on. I fantasized that this was just my normal day to day life with a man. He would buy me sexy lingerie, and I would wear it.

We went to the bar in his brother’s restaurant and had 2 or 3 drinks, then hit the streets. Even when we hooked up in the past, we never did any flirting, hand holding, kissing, etc. We both understood that we enjoyed each other privately, he was my man, and I was his girl, and that was our special secret.

That night was different. It was late, we knew no one on the streets, and had been going in and out of strip clubs while drinking and smoking pot. We even wound up in a Trans strip club, where we took a table close to the front and he even publicly treated me like I was his girl in some ways. He was rubbing my thighs and grabbing at my crotch from under the table, smiling, laughing, hugging, etc. A guy started hitting on me, and Brad told him to get the fuck away from me, I was his. I felt so safe with him.

When we walked out of that club, we hit the streets again, and he held my hand. It was nice to act uninhibited in public. As we walked, I sort of leaned my head on his shoulder. He led us off the main streets, where he took me into an alley, wrapped his arms around me like I was his girlfriend, and gave me a deep, long, tongue kiss as he was grabbing my ass cheeks. I had my arms around his shoulders and was rubbing his back and running my fingers through his hair.

He then pushed me up against the wall and pinned me to it, then began deep kissing me and grinding his throbbing cock into my crotch through his pants. It was by far the most romantic we had ever been with each other, in public or private. We were both seriously turned on with each other, it was real late, and we decided to go home and get in bed.

As soon as we closed the door to the house, he pushed me up against the wall and we started aggressively making out. He went straight down the backside of my pants and started grabbing ass, and I immediately began massaging his raging cock through his pants. After a few minutes he pulled one hand away and undid his belt, letting his pants fall to the ground.

Like a trained seal, I dropped to my knees and stuck his cock as far down my throat as it would go. He was groaning, I was moaning, things were really steamy and hot. I loved sucking his big cock and he loved the way I did it.

“Look at me when you suck my cock, baby,” he said, and I immediately locked eyes with him, taking his entire cock down my throat, and gazing up at him, with my nose in his pubes, and a tear running down each cheek.

“That’s more like it, you are an amazing cocksucking queen,” said Brad, and he grabbed both sides of my head and thrust his hips as hard as he could, almost like he was trying to choke me out.

He suggested that we get into bed, and I was all for it. I ran to the bathroom, put some of his brother’s girlfriend’s lipstick on, freshened up, stripped down to my bra and panties, and headed for the bedroom. He was laying there on top of the sheets, completely naked, and stroking his big cock. He smiled at me as I walked in, and I smiled back.

I laid down next to him and he immediately wrapped his arms around me and started kissing me. I was giddy with girly emotions flowing throughout my body and mind, breathing heavily, holding his cock in one hand, and one of his ass cheeks in the other. He continued kissing me, rubbing my tits through the bra with one hand, which was unexpectedly very arousing, and he ran the other hand down my back to my ass, under my panties, and firmly plunked his middle finger directly into my tight back pussy, which wasn’t lubricated at all. It hurt, but I didn’t care, and once he got it in there, he kept it in there to where it didn’t hurt anymore.

In my mind, I was thinking, “This is what it feels like to be a girl with a man, and I love it.” I was grabbing his cock, trying to get it to my mouth, and he accommodated me, changing positions so that I could reach it, and I gobbled it down passionately.

He started moving his finger in and out of my hole. He pulled it out and spit on his hand, then went back in. That felt much better, and I was in ecstasy. I kept sucking his cock like it was my only purpose in life, and began to taste his pre-cum, when he suddenly pulled it out of my mouth. He slapped me in the face with his cock, and I laughed. He slapped me with it again, harder, and I tried to take it into my mouth again, when he pulled away from me.

I was confused, and things got quiet, when out of nowhere, Brad grabbed me around my waist and turned me onto my stomach. I was still really turned on, and enjoying the feeling of being his submissive girl, when he pulled my panties down to my thighs, then spit on his hand and forcefully dug two fingers inside of me, and started breathing really heavily as I groaned in a mixture of pleasure and pain.

“Is everything ok, daddy?” I said to him, nervously, as I pulled my panties back up.

“That all depends,” he replied, as he worked his fingers in and out of me in rhythm, “I really want to fuck you.”

Here’s the thing, I really wanted him to fuck me, but I knew I wasn’t able to handle his giant cock, especially after drinking and not expecting this at all. I had experimented with tampons, cucumbers, and zucchini squash, and with each of those I used a dollop of Vaseline, and it still hurt.

I knew we had no lube, and I knew that we had never even gotten this far in our exploits. This was the first night that we really made out or kissed at all. We would grope each other, for the most part, then I would suck his cock while he played with my ass and rubbed my tits in my sissy bra and panties until he exploded into my mouth, and I swallowed it all. It was our routine, and we both knew it well.

“I don’t think we can do that, baby,” I said, caressing his thigh with my hand, while trying to work my way back to his crotch with my thirsty lips, “we can try some other time soon, I really want it, too.”

He got annoyed with my answer, apparently, and pushed me away from him, telling me to lay down on my tummy. I did what I was told.

“Just let me mess around back there, I promise I won’t stick it in,” said Brad, “I just want to rub my cock on your ass and fantasize.”

I was torn about what to say back to him. He knew I wanted it as bad as he did, but I wasn’t ready for that step on that night. Keep in mind, just a few months before this night I’m writing about, Magic Johnson told the world that he had contracted HIV, and that freaked everyone out. It made everyone feel like it could happen to them as well, but it didn’t stop me, Brad, or anyone else from feeling horny.

He said pretty please, and started caressing my ass cheeks on the outside of my panties with his hands, gripping each one and squeezing them, then spreading them. It felt intoxicatingly good, and got my heart rate to pick up a bit. I finally relented, but with ground rules.

“Ok, you can rub it around down there, but no penetration. Do we have a deal?”

He quickly agreed, and mounted me from behind. My legs were somewhat spread out, and he told me to put them together. I did what I was told. He straddled me as soon as I put my legs together, essentially locking me down under him. He was breathing heavy, and I could feel his rock hard cock bouncing on my ass cheeks, which really turned me on.

He took his cock and placed it on the outside of my panties, right down the crack of my backside, and started thumping me with it, then started making the motions of fucking me, and with each thrust, I felt more and more arousal. He was thick and hard. It really turned me on. I felt him gently pulling my panties down, and asked him to stop, but he didn’t, he just chuckled, and said,

“Let me just pull them down and rub my cock on your ass cheeks, I won’t stick it in, I swear.”

I told him no, but I wanted to say yes, and he knew it. After some more coaxing and persuasion, I told him ok, but that if he went for it, I would get up and leave. I was looking back over my shoulder at him as we were talking, and when I told him ok, he told me how adorable I looked in that position and came forward to deep French kiss me.

“Now put your face down, and relax,” he said, “I’m in control now, understand?”

He laughed a little bit, which made me laugh and relax, and I did what I was told. With that, he pulled my panties down to my thighs, and reasserted his position on me. He was gentle, as he spread my cheeks, and put the shaft of his cock right between them. I could feel the head on the small of my back, so I knew he wasn’t near my pussy hole, and with that, I relaxed.

I began daydreaming about all of the muted fantasies I had dreamt about for the past 5 or so years. Many of those fantasies involved the two of us, doing exactly what we were doing, except for real. He was grunting as he simulated fucking me, and moving back and forth so that I could feel when the head of his cock was right over my pussy hole. It felt amazing, and I was squirming in delight under him.

He fell off to my right side, and I heard him spit. Before I could really think about what was happening, I felt 2 of his fingers going inside of my pussy hole. I was loose in body and mind at the time, and let the waves of pleasure roll over me. I moaned lightly as he started to move his digits in and out of my hole, each time going a little deeper, and each time staying inside of me a little longer.

I spread my legs a little bit more to give him more space to work in, which he liked. I could feel his warm, stiff cock on my upper thigh and outer ass cheek, as he began finger fucking me at an accelerated pace. I had my eyes closed, and was wiggling under him in an effort to spread my cheeks a little more for him.

“Daddy, can you continue doing that, but bring your cock to my lips?” I asked, in between heated breaths.

He obliged, turned his body around, while keeping his fingers firmly in my ass, and delivering his cock directly to my lips. I took as much of it as I could into my mouth, and started bobbing up and down on it as deep as I could go. He started finger fucking me again, this time getting deeper than his knuckles, and started throat fucking me with his rock hard dick. I don’t know why I loved this feeling so much, but I felt like I could do it for the rest of my life and it would be a life well spent.

He started breathing heavier, which in turn made me breathe heavier, and then he found my pleasure spot. I didn’t know it was my pleasure spot, or that such a thing existed inside of a sissy pussy, but it definitely existed, and it definitely made me moan loudly. He recognized my arousal, and started pressing his fingers into the spot and holding them there.

I started bumping back on his fingers with my pussy, and sucking his cock as passionately as I could. He kept his fingers inside of me, and let me do the movement with my ass. I would back up, hold on his fingers and grind, then move forward. Wash, rinse, repeat, all while I was licking, sucking, and caressing his cock with my lips, tongue, and throat. Being fondled and teased by him felt so amazing. I’d never felt a cock so stiff, as it pumped in and out of my lips.

He pulled his fingers out of my pussy and pulled his cock out of my mouth, then went back to straddling me and letting his cock run right between my cheeks again. After a few minutes of this, I felt his hand run up my back, and grip my neck. I felt his grip tighten, then lock and push me down. My face was muffled in the pillow, as he repositioned himself on top of me.

I heard him spit again, but felt no fingers near my pussy, then it happened. With no grace or warning whatsoever, he stuck his throbbing bulbous wet cock head right between my cheeks, and directly into my tight, virgin pussy. I panicked and shrieked in pain, but that only made him tighten his grip on my neck and push my face down harder into the pillow. I tried to clinch my cheeks, but that only made him push into me harder. He went as deep inside of me as he could and just parked it there.

It was an excruciating pain, one I had never felt before, and he wasn’t moving. He laid down on top of me, on my back, with his cock still buried into my virgin pussy and put his hand over my mouth, then tried to calm me by talking dirty into my ear.

“I can’t help myself after playing with your tight little fuckhole while you sucked my cock,” he said. “I didn’t want to do this, I had to, and we share the blame for that, but I promise you will like it before it’s over with. Notice how I’m not moving? I’m keeping it there to get your pussy used to being filled.”

All this time that he was forcing himself inside of me and giving me tips on how to deal with the pain made me wonder how in the hell he had knowledge of this experience. He felt the tears coming out of my eyes and running onto his hand that he was using to silence me, and started talking into my ear again.

“Those tears will be happy tears soon enough, baby. Just relax and let it happen. I know you want it as bad as me.”

He wasn’t wrong, I did want it badly, but this wasn’t how I envisioned the first time being for me. I imagined lingerie, rose petals, lube, toys, sexy music, and so forth. The biggest issue I had was that I wasn’t given a choice in the matter. In a moment of reflection that I’m having as I write this, I am realizing that being raped is perhaps the most female adjacent event that I have ever experienced.

I was stronger than most women, and could have tried to fight back, but I had accepted the role of being sexually inferior to him, and called him various names like daddy, and baby. I knew he liked all of that, and I liked being called bitch and cock slut and so forth by him. We were friends and played in a band together. Our kinky secret hookups were just part of the territory, and those two worlds could never collide.

Listen to me, even now I’m trying to rationalize and romanticize the situation, and not make it into what it actually was. This was a violent, animalistic act being carried out by a person I loved and trusted against my will. He knew I had dreamed about him fucking me. In the past I had told him I dreamed about him fucking me. I had shared my innermost thoughts and desires with him, all while dressing up like a girl and sucking his cock.

I’m turning this event into a full page of this story, when the reality was that the whole thing was over in about 3 or 4 minutes, and half of that time was spent with him on top of me not moving, with is cock buried as far into my boi pussy as it could go, and just sitting there.

As he finally began to pull his cock out, it felt like my entire insides were coming out along with it. He got to the point where it was just his head in me, then he pushed it back in, and I let out an agonizing yelp, so he stopped again, deep in me, and began whispering.

“You’ve got to loosen up, baby,” he said, as he nibbled on my earlobe, “first comes pain, then comes pleasure,” and he pulled back again, this time not as far, then thrust into me.

I thought it was odd that he knew these things. I thought we were taking this journey together.

“How do you know what I need to do, baby?” I asked, genuinely confused. Perhaps he was experienced with fucking sissies?

“I know because I fucked Ashley in the ass when we were dating,” he said.

Ashley was his girlfriend for 2 years. He told me about all kinds of times that they had fucked in various places, and in different situations, but he never mentioned anal. It made sense, though, because I know that Ashley loved his dick, and was jealous of the friendship Brad and I had. I think that was one of the reasons he broke up with her.

It turns out he was right, it didn’t hurt as bad that time, and I made a slightly pleasurable moan, which made him grunt with excitement, and he began giving it to me at a slow pace. In, out, in, out, in, out, until I felt my sugar walls relax. I began to push back on him, and this turned him on. He got off of my back and gave me space to wiggle, which I did, and that made him really excited. He positioned himself over me, and stood up on his knees, still pumping slowly inside of me.

He took his hands and spread my ass cheeks as far open as he could, and I felt my pussy widen. It was still extremely tight, but there was no more instinctual physical resistance. This was happening, and even though it hurt like hell, and started against my wishes, the only way it was going to end was if I was able to fuck my way out of it.

Everything went into a higher gear when I felt his hands gripping my hips. To me, there was always something so hot about a guy grabbing a girls hips as she rocked herself back and forth while taking his cock. As a sissy girl, this was an extremely feminine feeling to me. I started breathing heavier and pushing back at him, which in turn made him push harder into me, and we achieved a rhythm of sorts that made it more pleasurable, for what that was worth.

He picked up the pace tremendously, I felt him nearing his end, and so I started bouncing off of his cock as much as I possibly could to get him to cum. He began thrusting harder and harder until he exploded. He left his cock as deep inside of me as he could, and screamed when he started cumming. I could feel warm, gooey fluids filling my pussy up, which made me scream in equal parts pleasure and pain, just as he told me I would.

He stayed inside of me until he reached his end. Feeling his cock being pulled out of me after he came was a mind blowing feeling. Cum and fluids started dribbling out of my quivering boy cunt and down my inner thighs. I stayed in the face down, ass up position trying to catch my breath and letting the senses in my body stop tingling.

I looked back from between my legs to see if I could see him, but he was nowhere to be found. I noticed that my panties were still down around my knees, so I pulled them up and laid down. When I did so, I felt them gushing with fluids from my pussy that was still experiencing spasms from what had just happened. I was still keeping my face down, and trying not to be emotional about what had just happened. My panties were drenched in his cum, and noticed that my clitty had also exploded during the activities, but I didn’t even have time to enjoy it as it was happening.

I heard the shower turn on, so I turned myself over and tried to maintain a sense of normalcy about everything. Coming to grips with the fact that I had just been raped by my friend, my secret gay friend, was a very weird experience. The range of emotions was all over the place. I got up to go to the bathroom, and noticed that I was walking like a girl who had just been spit roasted by a giant cock. It was sort of a turn on, if that makes any sense?

When I sat down on the toilet to pee, I dropped my panties down to my ankles, and that’s when I noticed blood in the gusset, along with gobs of cum, and other bodily fluids that I’d rather not discuss. As I started to pee, I also started to discharge fluids uncontrollably from my violated, and no longer virgin pussy. This would continue all through the night, and into the next day.

I got emotional about it, and got into the shower to clean myself up. When I came out, he was asleep on the bed. He had laid a satin babydoll nightie out for me, and I put it on, before getting in bed and curling up next to him. I put his sleeping arm around my body, and gave him a kiss, but he didn’t respond at all. I laid there with my head on his shoulder and went from comfort to crying for the rest of the night. His hand reached over and grabbed me by my left tit and he squeezed it. I fell asleep.

The next morning was awkward. Remnants of our crazy night were scattered throughout the room. My soiled panties were on the ground, there was blood on the sheets, and he threw them in the washing machine, but we didn’t speak much. There were a series of smiles between us, and he comforted me once by kissing the top of my head and wrapping his arm around my neck for a few minutes, but that was it.

He had really torn my tight virgin pussy up. We were playing another show with the band that night, and I had to run off the stage to go to the bathroom, because I felt like I was about to drip all over the place onstage, and all of my ability to clutch my cheeks was still lost.

I never confronted him about it, and we didn’t see each other for a few days after that last gig. A week or so went by, and we had more or less returned to our normal public relationship in front of everyone. We didn’t hook up for about two months after that night, and when we did, I still neglected to say anything. I just sucked his cock and swallowed his cum like I always did, while he played with my ass and pushed my head down on him.

This would change in the future, and I’ll write about it as well, but this was the story of losing my virginity against my will, further cementing my mental status as a sissy slut cum whore for men