Buxom Redhead Has Her Cherry Popped

By the time I lost my virginity to my gorgeous long-term girlfriend, who was a virgin herself, I was bursting with excitement...in more ways than one. It took us almost four years to consummate the relationship—for one big reason—but the night we shared, for all the pain and awkwardness, is seared into my memory forever. Before I get to that night, though, let me rewind things and introduce you to my Jenny.

Jenny and I met during our senior year of high school, after her family and she moved into my hometown from out of state. Both of us born on the same day and each of us just weeks past having turned 18, our attraction was sudden, mutual and almost overwhelmingly intense. The first time I saw her, she was sitting on one of the benches outside the school building and her form triggered an aching yearning deep in my loins.

Jenny was a stunningly sexy creature. Her hair was a fiery red and its natural waves bounced fetchingly when she walked. Her skin was very fair with a sprinkling of light freckles across her nose, cheeks and forehead, as well as along her upper chest. Her full, pendulous natural breasts burst from every top in her wardrobe. They would almost seem to say, mockingly, "You've got to be kidding me," as a button-up shirt would try to contain them. Her butt was big and round but firm nonetheless, perfectly complementing her curvaceous, feminine frame.

On this day...the day we met...Jenny wore a white tank top—out of which her freckle-speckled cleavage spilled—and snug-fitting blue jeans. The mere sight of her turned me on so much that I felt kinda unsteady on my feet...a little shaky, almost, and very nervous. I pondered whether to approach her and, if I did, what to say. I guess I was feeling unusually courageous, because I walked over to the bench and introduced myself, hoping she couldn't hear the pounding heartbeat that echoed in my ears and didn't notice my warm, flushed face.

Jenny told me much later, to my sincere surprise, that she'd spotted me earlier that same day and she'd been moistened by the sight of a guy who, physically speaking, seemed to have been ripped from her fantasies. I was an olive-skinned 18-year-old guy with well-groomed stubble on my face and thick black hair that I wore longer and slicked back. A lifelong athlete but not really one for team sports, my physique was heavily muscled and perfectly toned, although my six pack and pectorals were obscured by brownish chest hair that went from collarbone to groin. Six feet tall and the kind of guy into whose arms a girl could disappear, I was wearing a T-shirt and some jeans...very loose fitting, as always.

Without getting into all the details of our first conversation, which—surprise!—was a little awkward, Jenny and I found that, apart from the libidinous feelings we shared, we also had similar personalities and a number of common interests. Both of us wanted to go to college locally, and we each had an interest in pursuing English...maybe even becoming teachers. Although I liked poetry and creative writing and she adored Shakespeare, it was still more common ground than I could have imagined when I had been standing there, turning over in my mind whether to say hi to her.

What I didn't know at the time and wouldn't find out until later was that we were both—unbeknownst to each other—virgins, albeit for two very different reasons. Jenny's parents were very religious and, all throughout her girlhood, they'd made her attend evangelical Baptist services almost daily, plus participate in regular Bible study, which, they said, "brings you closer to the Lord" and "helps you not to fall prey to Satan's temptations." Although, as a young child, Jenny embraced her parents' fundamentalism and a church-centered life, she became disenchanted as she reached her teen years and sought freedom from her parents' oppressive piety.

When she was 16, she moved in with an aunt and uncle and began to assert her independence. Even simple things like, for example, being able—for the first time—to dress as she pleased was a joy for Jenny, who for far too long her parents had kept cloistered from perceived sources of "sin." However, even having renounced and rejected her upbringing, she, now 18 years old, still hadn't taken the step of expressing herself sexually...at least, not with a partner.

As for me, I was someone who had had a large group of male friends but who had never felt self-confident around the opposite sex. Back in those days, I'd hear rumors sometimes about this or that girl liking me—thinking I was hot or something—but I could never bring myself to approach her and ask her out. Why that was, I don't know, but it led me to live a chaste life while most of my friends and peers were exploring their budding sexuality. There was another elephant in the room, too...but we'll get to that in a bit.

Upon meeting, Jenny and I dated each other exclusively, finding that, as we peeled back each layer of the other's personality, we discovered deeper levels of compatibility. What hadn't changed from day one, though, was the viscerally lustful—almost animalistic—sexual attraction we shared for each other. She couldn't keep her hands off my arms and shoulders, loving to grip my muscled frame with her small, delicate digits. And I deliberately left the top few buttons of my shirts undone so she could run her fingers along my hirsute chest, letting them become caught and tangled. Meanwhile, I could feel my manhood firming whenever I smelled the citrusy scent of her perfume or glimpsed her voluptuous, almost unbelievably buxom figure.

It was inevitable, then, that we'd find our way into my bedroom within a month of our initial meeting. We lay entangled with each other, with Jenny's soft, plump, cool lips pressed against my hot mouth as my hands ran down her back and, eventually, grabbed her left buttock through her jeans and squeezed it gently. Her hair, usually so perfectly styled, was mussed from me running my hands through it; as we kissed, stray strands tickled my upper lip and nose, making me smirk and laugh as she, giggling, tried to brush them away.

I shifted my weight on top of her and moved into the missionary position, pressing my clothed groin into hers as we kissed deeply, our tongues probing each other's mouths. Our lusty kissing muffled Jenny's and my moans, whose intensity testified to a sexual desire that—bubbling for weeks—was about to reach a full-on boil. After a few moments, we sat up, looking at each other with more than a hint of bashfulness, and rose from the bed to undress.

Jenny was wearing a light blue sundress with spaghetti straps. She looked ravishing as the thin fabric stretched over her huge breasts, abundant cleavage peeking out. I took a strap in each hand and slowly slipped them from her shoulders, letting them fall lazily to the sides of her arms. I was tempted to bury my face into her soft bosom, but I held myself back. Taking the skirt in my hands, I lifted the dress up, over and off her nubile body.

The sight of Jenny in her bra and panties brought my erection to throbbing fullness. The bra, which could barely contain her 32H natural breasts, was white with pink and lavender accents; it matched her panties, through which I could see her reddish pubic hair. Her skin was radiant and flawless, the light freckling on her upper body only adding to her raw sex appeal.

I stepped behind Jenny and kissed the nape of her neck, breathing in the alluring scent. Rubbing my masculine hands against her soft shoulders, I teased her with gentle kisses on the side of her neck, near her earlobe and behind her ear as she gasped in sensual pleasure. Finally, I unclasped her bra, which contracted in relief against her back. I slipped it off and threw it to the floor, her ample endowment swinging free.

Jenny's creamy breasts were perfectly shaped: full, perky and identical in shape and angle. With such fair, delicate skin, her naked form had called to my mind the actress Christina Hendricks, whom I had at the time recently seen play Saffron in the show "Firefly." Large, puffy, pink areolas topped with thick, meaty, pencil-eraser nipples crowned her regal breasts. As I gazed at Jenny's figure, she looked down at herself, blushing a warm pink that radiated down to her neck.

I peeled off my shirt and undid my belt, thinking now was finally going to be the time when this bud, which had been dormant for so long, might finally burst into full bloom. I unbuttoned and unzipped my jeans and—sucking in a big gulp of air—I let my pants drop to the bedroom floor as Jenny watched on, holding her forearms against her chest.

"Oh my god...." she breathed, turning away from me and walking over to my closet door, her head hung slightly.

What I haven't mentioned—and what Jenny didn't know—was that I have an incredibly large penis...far larger, really, than I would have wanted. At the time, I usually wore compression shorts to hide the unsightly bulge of my eight-inch flaccid phallus, which was nearly five inches in circumference. Even though, underneath my loose, baggy jeans, I had had the shorts on, they could do very little to obscure the 12-inch-long, six-and-a-half-inch-circumference erection I was sporting. Looking down at myself, it appeared as though I had a foot-long cucumber strapped to my right leg.

Unsure of what to say, I looked toward Jenny, who was still standing near my closet door, her back to me. Within seconds, I could hear her softly weeping.

"Jenny... Jenny...," I said, walking over and, from behind, wrapping my arm around her shoulder. As soon as I did, though, she wrenched away from me angrily, still averting her eyes from mine.

"Jenny," I pleaded, "will you please look at me? Can we please talk?"

She turned in my direction, her face red with anger and her eyes lined with tears.

"Why didn't you tell me?" she demanded. "Why didn't you tell me about that?"

I stammered for a second, searching for an answer I didn't have.

"How am I supposed to have sex with that?" she fumed. "I'ma virgin, Tony! Do you realize what a dick like that would do to me? If I let you fuck me with that dick, you would tear me open."

"I'm sorry, Jenny!" I exclaimed. "I had no idea you were a virgin. If I had, I would have told you about me."

"We're not having sex," she said flatly, walking to pick up her bra. "It's not happening."

Backing up from her and taking a seat on the bed—the bed where, only moments earlier, we'd been passionately kissing—I made my confession. "I..." I began, "...I'm a virgin, too."

Slipping back into her sundress, Jenny looked at me quizzically for a long moment before she responded.

"I'm leaving," she said.

I called her a dozen times that evening, getting voicemail each time but never knowing what message to leave her. Honestly, had she answered, I wouldn't really have known what to say. The next day, though, Jenny called me.

"Thanks for calling me back," I said. "I'm really sorry, Jenny. I hate what happened yesterday."

"You're a virgin?" she asked, her question taking me by surprise.

"Yes," I said, "and I didn't know you were, otherwise we would have talked about what you saw before I took you to my bedroom."

"Look, I'm sorry I freaked out," she said. "You can't help how you're built."

"Yes, but...," I began, before she interrupted me.

"I've always heard your first time hurts a lot...and that's with normal guys," she continued. "Your dick is massive...it looked like it's a foot long."

"I understand...," I said, before being cut off again.

"Tony, I care about you a lot," Jenny stated. "Plus, you're a really hot guy. And I don't want to throw the last month away. Let's just, kinda, not do the sex thing for a while and we'll see how it goes."

As much as I desperately wanted to lose my virginity, it was far more important to me to keep my relationship with Jenny, so I told her that was fine with me and we could put off the whole sex issue for as long as she wanted. I didn't realize it was gonna be four years, though....

Oh, don't get me wrong. Once Jenny and I went to college together—both of us English majors—we brought things to a physically intimate level, including lots of erotic touching and frequent oral sex...even the use of some sex toys. But we never even approached the subject of penetration. Hell, oral sex was a challenge in itself.

The first time Jenny sucked me, I was lying near the foot of the bed, with my feet resting on the floor and her on the ground between my legs. My hard cock rested against my torso, throbbing in anticipation and already drizzling pre-cum. Holding my manhood with both hands—one on top of the other—Jenny pulled it from my body so it stood proudly in the air. Rising to her feet, leaning over and opening her mouth wide, she took in the cockhead; her hot, wet tongue glided against the underside of the glans, sending shivers up and down my spine.

Jenny sucked the head and just a bit of the shaft, taking in incrementally more over a few minutes that, for me, were pure ecstasy. I could already feel stirring in my proportionally huge balls to signal an orgasm wasn't far off. Just then, she gagged and coughed; she lifted her head off my saliva-spattered dick, which thwacked against my upper abs.

"It's a lot," she said, wiping moisture from her eyes and taking a few breaths. "I can barely get it."

Over time, though, she found that her mouth became more accommodating, sucking four or five inches while she used both hands to stroke me off. She confided one night that she loved the way my hot meat felt when she clasped her hands around it with her fingers interlaced.

Even though I was a college man with a long-term girlfriend, remember how sexually inexperienced I was at the time and, therefore, how easy it would have been to bring me to orgasm. Within minutes of taking my cock into her mouth, Jenny would pull away at my warning to avoid the volcanic semen eruption my every orgasm brought.

It was on one of the last days before summer break ended and we were to begin our senior year that, finally, Jenny decided it was time for us to consummate a romance that, sexually speaking, had been idling for years.

"Tony, I want to feel you inside me," she said as we lay side by side on our bed that night. "I want to know what it's like to have your dick inside my body."

"Are you sure?" I asked, rolling toward her but trying not to betray my palpable exhilaration. "Are you ready?"

Jenny nodded affirmatively in response, seconds later adding, "Umhmm."

"Now?" I asked her, already feeling my shaft starting to grow heavy with arousal.

She sat up a bit, leaning her neck and shoulders against the wooden headboard. Her cleavage beckoned to me from her little pink nightie. "Umhmm," she repeated.

I peeled off my T-shirt and pulled off my gym shorts, my oversized endowment flopping against my hip. Jenny slid back down onto the bed and I took her into my arms, hungrily kissing her eager mouth and grabbing her body with ferocious abandon. Through her nightie, I cupped her breasts, which overflowed into my grasping hands; her hard, protruding nipples scraped through the fabric against my palms. I had already become almost fully aroused and I began to feel almost frenzied in my passion.

Rather than slipping the nightie over Jenny's head, I literally ripped it from her body, the nightgown tearing straight up the back and leaving her only in a pair of little white panties. I pinned her against the bed, missionary style, and mashed my mouth into Jenny's, kissing her desperately. Even with her panties still on, I could feel right through them how wet she was as my pulsing cock rubbed insistently against her warm, inviting womanhood.

I slid the panties off, revealing a fiery red thatch of pubic hair that was slick with Jenny's sweet, succulent juices. Using both hands, she pushed my head down to her quivering pussy, wanting to feel my tongue caressing her every fold. For just a moment, I looked at her virginal little rosebud before descending on it, lapping greedily as she bucked and moaned. I turned my eyes upward to see Jenny grabbing at her breasts and squeezing her meaty nipples between the thumb and forefinger.

I spread her pussy lips and attacked her clit with long, vigorous licks, prompting Jenny to gasp and nearly pull away. I grabbed her hips, though, and smushed my face between her legs, pressing my tongue aggressively into her most sensitive spot as she squealed in unbridled rapture. She was absolutely soaked by this point, and tasting every last drop made my hard-on feel like it was about to burst.

"Baby...," Jenny gasped. "Baby...." She shrieked in ecstasy, building to an orgasm.

I pulled back and, once again, eyed her virginal, achingly tight womanhood. Giving it one last lick, I began to tease her clit with my forefinger while gently tugging at her pussy lip with my mouth. Her vagina reddened as I pulled at the lip and then released it with a lightthwack!as Jenny wriggled under my grip. I moved from right to left, pulling gently while also fingering her fully engorged nub.

After a few minutes, I knew it was finally time. With my cock rock hard, veins pulsating along the shaft, I got up wordlessly and went to the adjoining bathroom to get some lube. I slathered it all over my rod, which was already dripping pre-cum, and brought the tube back with me to the bedside.

In the few moments I was gone, Jenny had become noticeably more nervous, so I wasn't surprised to hear her say, when I got back into bed, "Tony...please, please be gentle."

"I promise," I said. "Let your body relax. Let the tension go out. I'm gonna go real, real slow."

Smearing some lube onto her vagina and rubbing the rest onto my already-coated shaft, I climbed on top of Jenny and lined myself up. I could feel her shaking beneath me and, to be honest, I was shaky, too.

"I love you, Jenny," I said, gazing into her ocean blue eyes.

"I love you, too, Tony," she said, peering up at me.

Holding my cock firmly in my hand, I probed for her tense opening and, feeling it, thrust in. Jenny cried out sharply as I penetrated, her hymen offering futile resistance to my bulbous cockhead. She sobbed as I split her open, obliterating her maidenhead in a single thrust.

Her viselike tightness around the couple inches that were inside her was almost uncomfortable for me...let alone for her. Jenny was crying hysterically and, to be frank, I felt terrible. I hated to be hurting her so much.

"Jenny, is it all right?" I asked, her deeply pained expression concerning me.

"Tony, you're tearing me open," she sobbed. "Tony, it hurts!"

"Let's just stop," I said, defeated.

Jenny winced as I pulled my dick out. I knelt on the end of the bed, feeling vaguely nauseous. Her inflamed vagina was bleeding rather heavily as she lay there. The blood pooled between her legs on our fine white linens.

Smearing the tears away, Jenny sat up and tried to calm herself. After a minute, she exhaled and looked at me.

"Tony, let's finish," she said. "The worst part's over."

She continued, "I love you, and I want us to be together...toreallybe together...in every way."

"Is your vagina OK?" I asked, eying the bloody sheets.

"It's gonna be fine," she said, lying back down. "Come on...let's go."

With slight hesitation, I mounted her again and waited for my hardness to return. Cupping her bountiful breasts from both sides, I pressed them together, smothering myself in her mammaries. I took her hard nipples in my mouth and sucked on them, biting gently and using my tongue to flick them. Within seconds, I was as hard as before.

I gripped my cock, now coated in a mix of vaginal fluid, lube and blood, and surged inside Jenny once again, becoming enveloped in her wet, velvety warmth. She gasped at my member's invasion, her whimpers quickly escalating to soft but continuous crying. I stayed still for a moment, holding myself there as, very slowly, the tension in her body diminished. Eventually, I was able to move more easily.