First Virgin Boy

In my early twenties, I dated a guy named Terry. He was a nice enough person, very respectful and polite. He was my age and not the typical bad guy type that, for some reason, I seemed to attract. I began dating him and soon realized he was on the more serious side. Honestly, I didn't expect that he could hold my attention for more than a couple of dates.

After somewhat of a wild start on my sexual journey, I reached a point of self-respect, and I had established a few ground rules for myself that I tried to follow. The first rule was that I tried not to have sex on the first date! Well, I tried anyway. If I managed to get by that crucial rule, I would make up a few more hypothetical rules.

First dates were limited to heavy kissing only. Second dates are limited to touching and exploring. I would allow my date to touch my breasts, and I would go no further than rubbing his groin through his pants. The third date maybe a hand job. The fourth date was possibly a blowjob, and if we made it to the fifth date, there were no limits. I thought these were reasonable limits for semi-nice girls, which I considered myself to be.

I remember telling several dates these rules, but honestly, I don't ever recall a time when I was able to stick to them, except with Terry.

My first date with Terry ended with us just kissing and making out in his car. It was all pretty tame and controlled overall. He was polite and seemed to respect the limits and restrictions I was trying to follow.

After our second date, we again began to make out in his car. As things started to heat up with Terry, I reached into his pants to do an assessment of his manhood. I liked what I felt, as it appeared to be a good size and worthy of a third date. Never being the patient type, I unzipped his pants and pulled out his cock. Yes, I know I broke my second date rule.

As I began to play with my new toy, Terry stopped me and said he had something important to tell me. 

"Really, I'm stroking your cock, and you want to stop and talk." I quizzed him. This was a first for me.

He sheepishly told me he was a virgin! "What! Really!" He now had my attention. I wasn't sure if I believed him. I thought maybe he was playing games to entice me into having sex with him. He was a good-looking guy but a bit on the shy side, so maybe I could see it. I guess I must have overreacted, as he immediately went limp. I apologized, and that was pretty much the end of the date.

I wasn't sure what to make of it. Is this good or bad? Should I go on a third date or run?

The next day, I called my friend Jenny. She always had answers. I told her everything and eagerly waited to hear her take on the situation. Not to be mean, but we did have a good laugh over it. Jenny had never been with a virgin before. We both pondered over it, and the more we discussed it, the more intrigued we both became. We jokingly came up with the term "Virgin Boy."

Jenny pointed out that guys think about sex hundreds of times a day. So if I were his first, he would probably think of me every day for the rest of his life. Wow, what an emotionally powerful thought that was.

Jenny went on the explain. "Imagine being his very first, the first girl he has sex with. You will always be remembered as 'the one'. The one he lost his virginity to. You will always be special to him. You will forever be engraved in his memory. Even when he gets married, when he is forty and is mindlessly daydreaming on his drive to work, when he gets old and reminisces, it will always be you that he thinks of when he thinks of his very first time."

The more we talked about it, the more we realized what a great opportunity this was. I think the thought of taking his virginity was turning us both on. By the end of the evening with Jenny, it was decided I would be his first. But we also agreed that it had to be special, not just a quick hump in the car. This was becoming a huge responsibility for me. I had to do it right. I felt an obligation to make it special.

Jenny was dying to meet Terry, so when he called for a third date, I told him that Jenny would be joining us. We all met at a bar, and Jenny loved him. She gave me her approval but also had a suggestion.

"How about for the first time he has a threesome with both of us? How special and memorable would that be?"

I had threesomes with Jenny before during vacations, so it wasn't out of the question. I told her I would have to think about it. I did have concerns, though.

A threesome sounded like a great idea, but I knew that Terry would end up remembering Jenny and not me. Jenny was a blonde bombshell. She was gorgeous and outgoing. Guys were drawn to her like magnets; that's one of the reasons I loved hanging around with Jenny. She could be overbearing, too. Sure, Terry would love to have sex with Jenny, but what about me? What about me being "the one"?

As the weeks went on, I was doing my best to refrain from having sex with Terry. He was cute and nice, but really, he wasn't anything special; he was too serious for me. But Terry was a virgin, and this made him special to me. Taking his virginity was all I could think of. If he wasn't a virgin, I'm sure there wouldn't have been a third date. He was in my head, or was it his virginity that was in my head? I was now determined to take his virginity.

Up until this point, I had dated older guys, and I was having sex on a fairly regular basis. With Terry, I was not doing well without sex. Terry thought I was the good girl type by not having sex. Yes, I was sweet and innocent-looking. But the lack of sex and the erotic thoughts about taking a young man's virginity were driving me crazy. Self-gratification definitely increased during this waiting period.

I finally told Jenny that I wanted Terry for myself. I wanted him to remember me, not Jenny and that other girl. Besides, I had been going without sex for weeks. I needed his full attention. Jenny seemed a bit disappointed, but she understood.

Jenny and I came up with a plan. As both Terry and I still lived at home, she suggested a weekend away in Niagara Falls. The honeymoon capital of North America--how appropriate was that?

Terry agreed, and I was so excited. How could I make this special event even better?

Leading up to the weekend, I daydreamed about how it all would play out. Would he ejaculate before we even started? Should I tease him, or maybe just jump him? What should I wear? It was all I could think of. I was horny as hell in anticipation.

I bought a new nightie for the occasion. There really wasn't much to it. It was short, sheer, and low-cut; not much was left to the imagination.

The day finally came. The long drive to Niagara Falls was filled with sexual tension. We chatted and joked during the drive, but my mind was racing. I couldn't believe how aroused I was. I don't think I ever thought about an impending sexual act as much as I did with Terry. I tried to rationalize it; after all, we all lose our virginity at some point, but psychologically, this had become a big deal for me. Maybe because my virginity was taken from me by a man ten years older than me who was only concerned about his own sexual gratification.

The shoe was now on the other foot. It was my responsibility to make sure Terry's loss of his virginity was a memorable and wonderful experience. Damn, I was so thoughtful.

We arrived at our destination and checked into a cheap motel. I will always remember the name "The Rainbow Motel." Terry was eager to begin and began groping me as soon as we entered the room, but I quickly put a stop to it. I had a plan; this was going to be a slow seduction. We unpacked, freshened up, and went to get a bite to eat. No alcohol for either of us; I wanted him to remember this special night.

Once we got back to the room, we sat on the edge of the bed and started kissing. As things began to heat up, I told him to get naked and in bed. I went into the bathroom to slip into my nightie. I slowly walked out of the bathroom and around the bed to make sure he got a good look.

I dimmed the lights but kept the room bright enough so that he could see everything that was about to happen to him.

I could see his arousal as the bed sheet was poking up like a tent. I slowly and sensually touched him as I stood over him. I told him he wasn't allowed to touch me. The lingerie I was wearing was totally sheer, so I wasn't hiding anything. I could feel my nipples harden as they brushed against the sheer material.

I slowly pulled back the sheets and crawled into bed with him. His cock was standing to full attention as he lay there. I could see he trimmed his pubic hair for the occasion. How sweet.

I reached down and grasped his cock in my hand. I squeezed it tight as I stared at it. I could feel the pulsating blood as it gushed through his veins. I felt a sense of power as his virgin cock throbbed in my tight grip. After many weeks of planning and anticipation, the time had finally arrived. His virginity was in my hand. No pun is intended.

I slowly began stroking him. I was very conscious of the possibility of him pre-ejaculating at my touch. I proceeded with caution. I didn't want to overstimulate him. As I stoked him, I could hear his breathing picking up. I slowed down and began to coach him. I wanted this to last. I was in total control, and I loved the feeling it gave me.

I had thought it best to proceed and give him his first blowjob before he exploded in my hand. I slowly and seductively began kissing and licking his beautiful cock. I was exploring his balls with my tiny fingers. I slowly lowered my mouth onto the tip of his cock and began slowly bobbing up and down, taking more of him inside of my mouth with every stroke. He was doing great, and by now I was getting right into it. I began stroking and sucking his cock vigorously. I then moved down and began sucking and licking his balls. I placed one of his balls in my mouth as I stroked him hard and fast.

I was hot and horny as hell by now, and he was getting the full treatment. I wanted him to cum in my mouth, and I wanted to swallow his first blowjob load. This was all part of my plan.

Despite my best efforts, he wasn't ejaculating! This was not what I was expecting, but I carried on.

Puzzled by his stamina I decided it was time for me to take his virginity. I was so wet with anticipation. I pulled my nightie off, so I was completely naked for him. I was going to make this special for him. I already had decided I wasn't going to use any protection to diminish the feeling, bareback only. I wanted him to feel just how good sex can be. I proceeded to mount him. Ever so slowly, I wanted him to feel every inch of me as I slowly lowered myself onto his hard-throbbing cock. I was soaking wet as I easily engulfed his entire cock deep inside of me. He grabbed and squeezed my breasts. My nipples were swollen and erect. I was primed and ready.

"Oh, gawd, that feels good." I moaned as I lowered myself onto him.

Slowly, I began riding him. I was taking it slow and easy, as I didn't want him to cum too fast. It felt so good to have his cock inside of me. The thought of finally taking his virginity was too much. He had barely entered me when I immediately began having an orgasm. I shook and quivered as I began riding him faster.

OMG, it was me that was pre-ejaculating and not him. Terry thrust deeply and pulled on my nipples as I let out a deep moan.

"Oooh yes... don't stop," I whimpered, finally letting out my built-up sexual frustration.

I was still deeply implanted on top of Terry as I regained my voice. He was still rock hard, so I continued to ride him. Soon, I was riding him like crazy. I was wildly bouncing on him as he had a tight hold of my hips, thrusting me down on his cock. He was giving it right back to me. I was riding him so hard and violently that I was pretty sure something was going to break. Was it going to be the bed or his cock?

I couldn't believe he wasn't ejaculating. I was so aroused about taking his virginity that I came once again. This time, it was even more powerful than the first. My whole body shook as I had violent spasms. I let out a loud, deep moan as I had an orgasmic eruption. In my twenties, it was very rare that I climaxed, so having two orgasms on the first go was incredibly rare for me. My juices were flowing. I needed a good fuck after going without sex for so long, and he was giving it to me.

Then it hit me. What's going on here? If he really is a virgin, why hasn't he ejaculated yet? I was convinced he had done this before. This couldn't possibly be his first time. Was I being doped? He just kept fucking me hard and fast. Eventually, I had to stop. I was confused, and yes, maybe even a bit angry for being lied to. 

"You said you were a virgin. Why aren't you cumming?" I demanded to know.

He apologized and explained that he was used to masturbating, and this felt different. It felt great, but just different. 

I suppose that is possible. I could tell by the look on his face that he was telling the truth.

After a bit of hugging and kissing, I went back to work and started with a nice long blowjob. I was determined not to stop until I swallowed his load. I got him to stoke his cock while I sucked him and manipulated his balls. With his assistance, he finally came in my mouth and gave me a huge load to swallow. 

Hurrah, success at last! I was proud of myself. I sucked and swallowed every last drop, and I even licked him clean. This was his first time, and I was being extra nice to him. I was making it special. I wanted to set the standard high for all future blowjobs. A standard that every other woman he slept with had to be compared to. Yeah, I gave him a great first blowjob!

Once he recovered, he mounted me missionary style and watched as he slowly entered me. We both began moving in rhythm as he fucked me. I began coaching him to fuck me harder; I could tell he was getting worked up, and it wouldn't be much longer now. As he was getting close, I told him to cum inside of me, saying that I wanted to feel his warm cum deep inside of me. He came hard and fast. I screamed out "yes, OMG, yes" as he filled me up with his warm virgin cum.

He made me work for it, but his virginity was finally mine. I will always be remembered as "The One." I think I was more thrilled than him.

That weekend, we had sex 22 times. Yes, I kept count. We were like newlyweds. Terry just couldn't get enough, and I never refused him. There was no way he would ever forget me after that weekend.

When I got home on Sunday night, I swear I was walking bowlegged. I was exhausted and sore. I couldn't wait to tell Jenny. I felt such a sense of accomplishment.

I was hooked on the sense of power, control, and adrenalin rush I had felt. The anticipation and buildup of finally taking his virginity. The epic orgasm I felt when I finally had his cock inside of me. The psychological pleasure I felt knowing I was forever special to someone. This memory will never be forgotten by either of us.

I wanted to do it again; I couldn't stop thinking about it. I wanted to experience another virgin boy.

Since then, I have experienced several virgin boys. Read my other stories.

PS: I continued to date Terry for a couple of months afterwards. During that time, he became quite proficient at sex. I was thrilled to be the experienced woman who taught him all about sex. It was quite a rush.

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