Losing My Virginity

I was a tomboy and, growing up, I seemed to get along with boys better than girls. But when my classmates transitioned into dating and romances, I was left on the sideline. Even though I was now 18, I guess the guys thought of me as a tomboy, not as a woman.

I didn't have any girlfriends to confide in, but I did have a best friend, Tom. Tom and his older brother Pete were over at my house one day, hanging out. Getting my courage up, I just point blank asked them why the guys didn't seem interested in me.

"Well, I don't know," Tom admitted. "You have a great personality and," he cleared his throat, "you have a nice body." I blushed. I was proud of my body - I had always been athletic, but my breasts had blossomed in the past few years - my mother had teased me that every few months I seemed to need a new bra. I was now a 34G and my full breasts were topped with large, swollen areolae and thick short nipples that became long and erect when I masturbated.

"I guess we just think of you like a sister," Pete told me.

"Oh great!" I laughed. "I have to find a guy who is into incest!"

Pete laughed and then became serious. "Well, and you could maybe dress a bit differently," he added, then dropped his eyes from my gaze.

I began to get angry, but then I remembered he was only trying to help.

"What do you mean?" I asked.

Tom jumped in. "Well, I remember when we were swimming last summer, it was the first time I had really seen your body properly," he stammered. "You sort of hide it under baggy clothes and it makes you look sort of fat. When we were swimming, it was really stunning to see how beautiful you are."

I smiled at his compliment and then I realized my bust line had probably grown a few inches since that last summer.

"Maybe the two of you can help me figure out which parts of my body to accentuate," I told them. I led the two brothers over to my bed and sat them down and then I closed the door so we wouldn't be disturbed.

"Don't say anything yet," I told them. I had a moment of panic, but then I decided to go ahead with my plan. I took off my baggy sweatshirt, revealing my plain white bra. Then, stepping out of my shoes, I removed my blue jeans, revealing my white cotton panties. I put my hands on my hips and stared at Tom and Pete.

"Um," Pete stammered. "I mean, it's all nice, I think." Tom nodded his head.

"Maybe this bra is too old-fashioned looking," I told them. Unclasping the three strong hooks in the back, I released the bra and removed it. My breasts tumbled out.

"Wow," Tom said. "I mean, if you really want to lose your virginity, I'd be happy to help out."

I smiled and pulled him to me, giving him a strong bear hug. Before he had a chance to rethink his offer, I was lifting his shirt over his head and kissing his chest. Tom loosened his belt and removed his pants and underwear in one motion. Meanwhile, Pete was sitting stupefied on the bed.

"I'm a virgin, so feel free to tell me what to do," I told Tom.

Tom eyed his brother Pete nervously. Pete had gotten off the bed and was also getting undressed. Tom began to speak but Pete interrupted him. "I'm a lot more experienced than Tom, so I'll show you the ropes," he told me. He was naked and his large cock was protruding from his body at a ninety-degree angle.

Pete led me away from Tom and positioned me on his knees. "It's important that you know how to suck cock," he told me. I opened my mouth and he began to thrust his cock in and out of my mouth. "Suck on it," he instructed me, "and swirl your tongue around it."

As I concentrated on sucking Pete's cock, I felt Tom's hands on my breasts. He was squeezing my breasts and pinching my nipples. Pete ignored his brother and continued to thrust in and out of my mouth.

"Okay," Pete told me, withdrawing his penis. "It's your turn now." He placed me on the bed and began to lightly kiss my thighs. Tom took advantage of this opening to straddle my chest. He pulled my breasts together around his erect cock and tried to thrust, but there was too much friction.

"I have some body lotion on my counter," I told him. He clambered off of me and quickly returned with the lotion. He placed the cold lotion directly into my cleavage and I winced from the cold, but I didn't say anything as I didn't want to distract him. Meanwhile, Pete's kisses and fluttering tongue were moving closer and closer to my pussy. I sighed expectantly of receiving oral sex for the first time in my life. I had masturbated to orgasm many times but had never received pleasure from another person.

Helping Tom out, I pushed my breasts together and he began to steadily fuck my breasts. As he thrust into me, he reached out and gently pinched my nipples. Meanwhile, Pete was fluttering his tongue up and down my labia, occasionally grazing my clitoral hood. Involuntarily, I began to moan.

After a few minutes, Pete lifted his head up as if to stop and instinctively, I reached around Tom and grabbed his head, pulling him back in. "Don't stop," I cried out, pulling him by his hair. Pete resumed his attentions and I released his hair and leaned my head back, enjoying the sensations of his tongue circling, but not directly touching, my clit.

After several minutes, I was overcome by the largest orgasm I had ever experienced. It rolled through me in waves and I cried out in joy as pleasure filled every cell of my body. Pete continued to lavish me with his tongue as the orgasm subsided.

For a moment, I wasn't sure what was happening and then I felt spurts of a hot liquid hitting my chin as at the same time, I felt Pete penetrating my vagina. I lifted my head to see Tom climaxing, his hot semen splashing against the underside of my chin. My head fell back as I began to feel Pete thrust harder into me, and I experienced the sensation of a man taking me entirely, his cock churning into and out of me, lifting me up back onto my hips with each thrust.

Tom rolled off of me and Pete, ignoring the pool of semen at the base of my neck and the streaks of ejaculate on my breast and chin, clasped me tightly and kissed me soulfully as he rammed into me repeatedly. I didn't experience an orgasm, but I felt a pleasurable sensation as he drove into me again and again.

"Are you on the pill?" he asked me.

"No, I gasped," realizing the reason for his question.

"Oh shit!" he cried out, pulling out of me.

"What should I do?" I asked him, in a panic, as he gripped his penis, trying to forestall his climax.

Without answering, he clambered forward and directed his penis into my mouth. I did my best to accommodate him, but he was even bigger than his brother Tom. I later learned he was over eight inches in length fully erect. His penis inserted safely into my mouth, Pete thrust deeply into me and I nearly gagged as his cock hit the back of my throat. He squeezed my breast roughly as he groaned and I felt waves of semen entering my mouth and throat. I did my best to contain it all, but I coughed, and semen sprayed out of my mouth onto Pete's leg and my chin. A rope of ejaculate splashed onto the side of my face.

I took Pete's cock back into my mouth and sucked out the remaining semen as best I could. Pete gently pet my face. Looking up at him, I could see the glisten of semen on his chest where he had pressed into his brother's ejaculate. I found that visual very sexy - it told me that Pete had wanted me so much that he had not paused to embrace me.

"I think we have time to show you more, if you'd like," Pete told me.

I leaned over to grab some kleenex to wipe the ejaculate off of my face and chest. "What do you have in mind?" I asked him.

"Well, have you tried anal?" he asked me.

I shook my head, no. Glancing over at Tom, I saw him stroking his again erect cock, eyeing me hungrily.

"Won't it hurt?"

"I'll be gentle," Pete noted, picking up the bottle of lotion.

Pete positioned me on all fours and lathered my asshole with lotion. He massaged my anus, ultimately inserting a finger into my ass. He fingered me shallowly at first, but then deeply drove his finger into my ass. I moaned slightly, involuntarily bucking my hips.

Meanwhile, Tom had positioned himself in front of me and placed his cock in front of my mouth. I parted my lips and Tom began to gently thrust his cock in and out of me. I limply left my mouth open so Tom could fuck my mouth and I concentrated on bucking my hips slowly back and forth against Pete's finger in my ass.

Pete removed his finger from my ass and then I felt the head of his penis pressing against my sphincter. I held still as he slowly and gently thrusted into me, my sphincter expanding to accommodate the head of his penis. Once the head of his penis was fully inside my ass, Pete gradually lengthened his strokes and slowly drove deeply into my ass. The sensation was incredible, the network of nerve endings around my ass were fully stimulated and, letting Tom's cock drop from my mouth, I lowered my head to the bed and moaned. Pete was now gripping my ass cheeks and beginning to fuck me more roughly.

Impulsively, I shouted, "I want both of you inside me!" Pete withdrew from me and I placed Tom on the bed so that I could mount him. Leaning forward, I received Pete's cock back into my ass. At first it was difficult to manage the two men at once. Finally, I concentrated on riding Tom's cock and let Pete adjust his pacing to my movements. The feeling of the two brothers penetrating me was incredible. "Dude, your balls are slapping against mine," Tom noted. The thought of the two brothers banging balls was turning me on and I began to orgasm. I stopped fucking Tom and collapsed onto his chest, shuddering as the orgasm rippled through me. As I collapsed onto Tom, Pete's cock popped out of my ass.

My ass was twitching, wanting Pete to penetrate me again, but he didn't re-enter. Instead, he lifted me off of Tom and rolled me onto my back. "I've not fucked these tits yet," he told me, grabbing my tits, which were still glazed with Tom's semen, and squeezing them around his cock. As he began to fuck my tits, Tom placed next to me and began to fuck my mouth. I was overwhelmed with the feeling of the two brothers' cocks penetrating my mouth and cleavage.

Pete was the first to climax. His first stream of ejaculate hit the edge of my cheek and splattered upward, spraying Tom's leg and my face. He then leaned forward and, grabbing his cock, jerked himself off onto my face. Tom continued to fuck my face, Pete's semen dripping onto my face and Tom's cock in thick globules. Pete groaned and I could feel a stream of semen shooting into my throat. I concentrated on sucking Tom's cock as he continued to climax in my mouth. Even as Tom was climaxing, Pete had moved forward and forced his cock into my mouth. I could feel the brothers' cocks side by side, Tom's still spasming in orgasm. I did my best to accommodate the two cocks, lathering them with my tongue as Tom's orgasm subsided.

Not only had I lost my virginity, but I had also had my first threesome. It wasn't my last, as the two brothers continued to visit their affections upon me.