Perverts 'R' Us

How I Lost My Virginity

By Danyealle ( 1st, Virg, cons, oral )

I was orphaned at the age of 6 when my parents were killed in an IRA firebomb. I spent the ages between 6 and 17 in a foster home. I graduated from high school at the age of 10, so I've been going to college since then.

Finally, at the age of 17, the lawyer in charge of the trust fund my parents left me found a guardian willing to take me in until I was 21, with the option of adopting me. He was a 30-year-old detective with the NYPD, named Phillip McGowan.

We got along just fine, and were very compatible. I am getting my doctorate in psychology, specifically deviant behavior, geared towards police work. I had a boyfriend when I moved in with him, a man named Kevin. It was made clear by me from the beginning that I didn't need a father; it wasn't what I wanted or needed. I wanted a big brother/friend. That is what Phil became to me.

Kevin wasn't in town very often, so we didn't get to see each other much, but we talked to each other on the phone frequently. Phil got along very well with all my friends, but he was very cool and reserved around Kevin. Everyone who knew Kevin, me included, called him either Big Daddy or Big Guy, except Phil. To Phil he was Kevin. At first I thought the age difference between us - Phil was 35 and I was 17 - was the reason for the coolness, but I soon found out that wasn't the case. For the life of me I couldn't figure out what the reason was! He would be his usual funny, sweet, kind, animated self until Kevin would show up, and then it was like a wall of ice would drop around him. I didn't think it was that he didn't like Kevin, he said that he liked him fine. I just couldn't figure it out.

I'm a 'sexy babe', as my male friends put it. I dress sexy and have the attitude, and in all honesty without make-up and in grungy clothes, I look all of 13.

Every since I moved in I have always been able to talk to Phil about anything at all. We discussed everything. He was one of the few people in this world I could talk to about my inner-most feelings. He was also only one of four people who knew that, for all my sexy body and attitude, I was still a virgin. He answered every question I asked him about sex, and he always answered honestly and discussed it in detail with me. He was always honest with me about everything.

Once in a while after work, Phil would have a few drinks. When he drank he never got violent or nasty, just mellower and funnier. I never felt threatened by him the way I have around some men who drink.

Kevin knew I was a virgin and hadn't pushed the issue of sex with me. That is why I like to go out with older men - they have their libidos under control for the most part, and know the meaning of the word "no." We got along fine and we enjoyed each other's company. We became friends and really got to know each other before the topic of sex even came up. The farthest it had ever gone was some really heavy petting and I had jerked him off a couple of times. But the issue was never pressed. I never felt pressured into doing anything that we did. It wasn't that I didn't have sexual desire - believe me, I did. Most of the time after our dates, I had to go home and masturbate to relieve myself. That's something I did three or four times a week anyways. The issue was that I was scared to "go all the way." I had held onto my virginity for so long that the thought of having sex scared me.

One night Mike was propped up on the couch, watching a basketball game. I flopped down on the sofa next to him and watched the game for a while. After the game was over, there really wasn't anything good on, so we started talking. He asked me how school was going and what I was doing in school. We discussed that for a while then we discussed some of the cases he was working on.

"Phil, there is something I need to ask you." I said, a little nervously. "Does it hurt the first time a woman has sex?"

He smiled at me, "I'm the wrong person to be asking that. I'm a man, not a woman. But from my understanding it does hurt, but how much depends on the woman a bit and how gentle the man is. Does that answer your question?"

"I think so."

"Is the reason you've held out for so long because you're worried it's going to hurt?"

I grinned, sheepishly, "Part of it. The other part is just the fear of the unknown, I guess."

He laughed, reached over and tousled my hair. "There's nothing wrong with that. Males and females are both scared and nervous the first time." He looked at me, "You thinking about losing it finally?"

I shrugged, "The hormones are taking over."

He laughed, "That happens at your age. I'm surprised that you've held out as long as you have. Most girls your age have had several partners."

That weekend I had a date with Kevin. We went out and had a good time. A little heavy petting and a hickey were as far as it went. He had me home by 2 AM. He walked me to the apartment door, gave me a kiss, and then left. I let myself into the apartment and put my jacket in the closet. I then headed to my room. I noticed Phil was still sitting on the sofa. That was unusual. He never waited up for me when I went out.

I wandered over to the sofa and sat beside him. He looked at me and smiled, "Have a good time?" He turned my head slightly and looked at the hickey. "I think that answered my question for me."

From the smell of his breath and the way his eyes looked I could tell that he had been drinking and a lot more than usual. To put it bluntly, he was bombed. I smiled at him, "Yeah, we had fun. Well, I'm going to head to bed." I leaned over, kissed him on the cheek and headed to my bedroom. I undressed, grabbed my night shirt and a clean pair of panties then went in and took a shower.

When I was done I got dressed then went into the bedroom and sat down at my vanity to brush my hair out. I was letting my mind wander and didn't hear the door open. Phil leaned against the doorjamb, folded his arms across his chest and said, "Was he good?"

I jumped a little bit, as he had startled me. I looked at him. "You scared me! I didn't hear you come in. What do you mean?"

"Just what I asked, was he good?" He said, with a strange look in his eye.

I just looked at him, bewildered, "I still don't know what you mean."

He stood up straight, put his hands in the front pockets of his jeans and looked at me then said, "I mean you fucked him and I wanted to know if he was any good."

I looked at him, mouth agape. "What is wrong with you? You don't know that we did anything, and even if we did it wouldn't be any of your business!"

He strolled over to stand by the vanity and looked down at me. "You obviously did something from the mark on your neck. You were just saying the other day that your hormones were kicking into high gear. So I figure with him being almost seven foot tall he has to have a pretty big cock. So how big is he and did it hurt?"

I stood up and looked at him. "I don't believe this! First, the size of his dick is none of your business. Second, and this is really none of your business, we didn't have sex."

I turned to walk away from him but he grabbed my arm, pushed me flat against the wall and stood in front of me, pressing tightly against me. "He isn't what you need, I am." Then crushed his lips down onto mine.

I struggled against him, trying to push him off me. Finally, he pulled his lips off mine and I was able to shove him away a bit. "What in the hell is wrong with you?" I said, looking up at him.

He looked down at me, "Not a god damned thing." He then crushed his lips back down on mine, reaching up and starting to feel my tits through my shirt.

I will be the first one to admit that Phil is handsome and a very sexy man. If he wasn't my guardian I could go for him. He took his lips off mine and started kissing my neck. With one hand he pushed my shirt up and started fondling my breasts. With his other hand he reached up and starting running his fingers through my hair. He was turning me on more than I already was. Every time I come home from a date with Kevin I am as horny as hell. I wanted Phil all along, but I didn't want it with a drunken man. I wanted him sober. I moaned a little then said, "I want you Phil, but not now - when you sober up."

That was like a splash of cold water on him. He pulled his hand off my chest and out of my hair. He looked at my face then down at the floor then looked away from me. "Oh god, Mickey, I'm so sorry. I don't know what came over me." He put his hands back in his pockets and walked out of my room. I heard the door to his room shut. I crawled into bed and soon fell into a troubled, fitful sleep.

The next morning I woke up and heard Phil moving around in the kitchen. When I came out of the bedroom he was just dishing up breakfast. I gave him the usual peck on the cheek and sat down to eat. All through the meal he wouldn't even look at me. He spent most of the rest of the day avoiding me. Finally, he was out watching TV and I came out and sat beside him. He mumbled something to me and I grabbed the remote and shut the TV off. "We need to talk, Phil." I said softly.

He looked down at the floor, "I am so sorry about last night. I was drunk. I know that's no excuse but I lost control."

"You wouldn't have done it at all if you weren't already thinking about it before you started drinking," I said softly.

He sighed. "You're right. I do want you. That is my problem with Kevin."

I smiled. "You're jealous."

"Yes, I'm jealous."

I took a hold of his hand and he looked at me, "Mickey can you forgive me and ever trust me again?"

I smiled at him, "Of course I can. Do you remember what I said to you last night?"

"Yes." He said, smiling at me. "Mickey, I'm sober now and I'm sorry about the rough way I treated you, but I still want you. Did you mean it when you said you wanted me too?"

"Yes, but I didn't want you drunk to where you would regret it in the morning. I also wanted a man that was in control of himself."

He bent over and tenderly kissed me. "I want to get one thing straight before we go any further. You're still a virgin, right?"

I reached up and stroked the side of his face. "Yes. I told you that last night, I didn't lie."

He pulled me over onto his lap, wrapped his arms around me and pulled me into a deep kiss. When he broke it off the kiss he stroked my hair and said, "Are you sure about this? If we make love, everything will change between us and we can't go back. I'm willing to take that chance and deal with the consequences. I want to make sure you are. If you have any doubts, nothing is going to happen." He reached and stroked the side of my face. "I want you to be sure, Mickey."

I laid my head on his shoulder and wrapped my arms around his neck. I'm sure, Phil. I want it to be special and with someone I care about. I can't think of anyone better than you."

He stood up and carried me to his bedroom then sat me on the edge of his bed. Standing back a little bit from the bed, he stripped down to his underwear. He then came back over to the bed and knelt between my legs. He started kissing me and stroking my hair. I reached up and wrapped my arms around his neck. After a couple of minutes he broke off the kiss and looked in my eyes. "Are you scared?"

I looked at him, "A little bit. I've never even been naked in front of a man before."

He touched the side of my face, "It's alright. I'm nervous too. I don't want to hurt you, and I want it to be special." He then kissed me again, then eased his hands down to the front of my shirt and started unbuttoning it. When he reached the waistband of my jeans he pulled the tail of the shirt out and unbuttoned the last two buttons. He then reached up and eased it off my shoulders, letting it fall to the bed. He then ran his hands across my naked shoulders and down my rib cage.

I shivered a little bit as he touched my naked flesh. He bent down and kissed me again. "You're so beautiful. Just relax, I won't hurt you." He then reached down, unbuttoned my jeans, and lowered the zipper. Then he reached up and hooked his fingers in the waistband and started to ease them down my hips. I laid flat on my back on the bed and arched my hips up so he could slide them off. When he got them off he dropped them to the floor.

The only things I was left wearing were my bra and panties. He made no move to take these off. He got up onto the bed and lay down beside me, pulling me into his arms, kissing me. Then he reached down and stated to rub up and down my stomach and ribs, staying between the boundaries of my bra and panties. He started kissing down my throat, working his way down to the valley of my cleavage. Reaching up to the front of my bra, he started unhooking it. He then opened it up, exposing my breasts, the nipples stiffening. He eased the straps down my arms and off. Then he bent down and started to lick and suck on my left tit, and play with the right one. After a couple of minutes, he switched. Then he got up on all fours, straddling my body. I reached up and started running my fingers through his thick, brown hair.

Phil then stared kissing and licking his way down my stomach until he reached my panties, then stopped. He then moved up to the head of the bed and lay down. He motioned for me to come up and lay beside him, which I did. He then reached down and grabbed his underwear, arched his hip and skinned them off.

Taking my hand he started to move it around on his hairy chest. Smiling at me he said, "Baby, touch me anywhere you want. Get used to my body." He then folded his arms behind his head. I rolled over onto my side and started to run my hand across his chest. My eyes kept wandering down to his erect cock. He and Kevin were the only two live men I had ever seen naked, of course I had seen plenty of pictures but it wasn't the same.

I finally let my hand wander down to his crotch. I ran my fingers through his course, curly pubic hair. Then I ran it down one of his thick thighs. I could feel the muscles work beneath the skin as I touched them. When I reached his knee, I moved over to the other leg and did the same thing. Finally I moved my hand back to his crotch. I ran the tip of my finger lightly over the top of his cock and down the underside. I then ran my finger lightly over his balls, feeling them twitch under my touch. Mike spread his legs farther apart so I could have easier access to him. I wrapped my hand around his dick and started to move it up and down. Looking up at him I asked, "Is this alright?"

He smiled and reached over and stroked my hair, "It's just fine."

"Show me how you like it, please?"

He reached down and wrapped his hand around mine, showing me what he liked, and kind of wringing the head of it on the upstroke. We kept this up for quite a while until Mike's breath was coming in short pants. He then pulled both our hands off of it. He rested for a couple minutes then propped himself up on one elbow and kissed me.

"Hmmm, we had to quit or I was going to cum." He gently pushed me onto my back. "Now I'm going to make you feel good." He got up on all fours and pulled my panties down, then off. Then, spreading my legs apart and laying down between them, he started to run his tongue up and down my slit.

I moaned and arched my hips up. Reaching down, I ran my fingers through his hair. God, it felt wonderful! I had never felt anything so good in my entire life. He soon had me writhing all over the bed and brought me to a powerful, head-swimming orgasm.

While I was recovering, Phil crawled up between my legs and propped them on his, then bent over, resting himself on his elbows above me. Leaning down, he kissed me softly, "Did that feel good, baby?"

I smiled, "Hmmm, there isn't a word in the English language to describe how good it felt."

"Would you like to try and have sex? Or aren't you ready for that yet?"

"Yes, I want to, but I am a little scared."

He stroked my hair softly, "Everything will be alright. I will be as gentle as I can, and if you want to stop just say so and it will stop. I don't want to hurt you, I want to make you feel good."

I looked up into his blue-green eyes, "Alright. Make love to me, Phil." I whispered softly.

I could feel him move one of his hands down between his legs as he kissed me tenderly. Then I could feel the head of his cock rubbing up and down my still-wet slit. Finally he rested the head of it against the opening and started to ease it inside, gently. I winced and tightened up a bit, it hurt.

He kissed me again, "Why don't you wrap your arms around my neck. Dig in if you need to, baby. Try to relax the best you can, it won't hurt as much if you are relaxed."

I wrapped my arms around his shoulders and did my best to relax as much as I could. Phil inched his way in as slow and easy as he could, trying his best not to hurt me.

It took him a long time to reach my hymen. Lying down almost flat on top of me, propped on up his forearms, he kissed me tenderly, "This is it, baby. Yell, scream, and dig in, anything you feel you need to do. I will be as gentle as I know how, but I imagine it's going to hurt."

I wrapped my arms more tightly around his shoulders, preparing for what was now going to become inevitable, more than a little frightened by what was to come.

He kissed me tenderly, and then started moving in and out slightly. Finally on the in-stroke, he slammed all the way through and buried himself all the way inside me. I dug my nails into his shoulders, screamed a little bit as the membrane ripped and felt tears fill my eyes and spill over to run down my cheeks.

Everything I had heard was true, it hurt like a son of a bitch. Phil pulled me tight to him, kissing me and stroking my hair. "It's all over, baby. You won't have to go through that again. Now we can work on it feeling good."

He held still for a long time, letting me get used to him and letting the pain ease up. When I was finally used to him and the pain had dulled, he slowly started to move in and out. After several minutes, the pain started to give way to feeling very good. After several more minutes, I started to urge him to go faster. He got back to the upright position, on his knees, pulled me closer to him and started moving faster and harder. I could see the sweat running off him in streams and hear his sharp pants.

He then reached down and started to rub my clit. That soon had me writhing all over under him, moaning and begging for more. He continued until a few minutes later when I came, hard.

He then bent back over, kissed me softly and started moving faster and faster until in a few more minutes he came, bathing my insides with his cum. He then collapsed on top of me, panting and gasping for air. Kissing the side of my face, he stroked my hair again.

"Mickey, that was good. Did you like it?"

I reached up and ran my fingers through his sweat soaked hair, "It was wonderful."

He rolled off me onto his side and pulled me close to him. I could see blood streaked on his cock. "I know it hurt, but I was as gentle as I knew how to be. You're the last person in the world I want to hurt."

I smiled, "Once I got over the pain, it felt wonderful."

He kissed me again. "Just lay there, I'll be right back." He went to the bathroom, returning with a washcloth and cleaned the blood off me. In a half an hour, we made love again, and this time it didn't hurt at all.

How_I_Lost_My_Virginity