Amys First Time 5

The look of pain on Amy's face was, at once, both worrisome and a huge turn-on. I had worked my cock half way into her virgin pussy when she cried out, "it hurts, it hurts!" I asked her if I should stop. "No," she said. "Give me a minute. I want to do this." I held still, caressed her pretty face and waited for the pain to subside. "Okay," she told me. "Keep going." I carefully pressed on, sliding in another inch. Amy took in a sharp breath through clenched teeth. "Oooh".

I pressed forward again, overcoming the last of her hymen's resistance. I was completely inside her. She continued breathing through pursed lips. I let her rest again. "That's it," I told her. "You're not a virgin any more." I kissed a single tear from her cheek.

"Does it get better?" she asked.

"I promise it does."

Amy, a 24-year-old elementary school teacher, was 6 years younger than me. We met at a party thrown by mutual friends. She was a transplanted Iowa farm girl, naive in every charming way. She was raised conservative and Christian. She had a sweet, innocent look about her, needed no makeup. She was a natural redhead with a freckled nose and paper white skin. She looked no more than seventeen and you'd swear if you saw her that you'd seen her before in a Norman Rockwell painting. She had a small body, nicely proportioned with small breasts and hips that flared out invitingly.

Amy and I had been seeing each other for about six months. Her move to the city had left her feeling isolated and lonely. By our third date, she told me she was a virgin, though I had already guessed that. I told her that she could remain a virgin for as long as she liked, that it wouldn't affect my desire to spend time getting to know her. The next time we were together we had a long make-out session on my couch after a dinner of Chinese takeout and a movie.

I whispered into Amy's ear, after breaking a long kiss, that there are lots of ways we could enjoy each other without having intercourse and asked if she trusted me. She said she was willing to let me show her. We ended up in bed together that night beginning with a long hour of foreplay before I gave her her first orgasm from being stimulated orally. She was initially very shy about letting me near her labia, though she had seemed to relish the attention I had lavished on her small breasts.

I told Amy how beautiful her pussy was, as I kissed the lips of her vagina for the first time. I licked slowly and deliberately, taking my time. She seemed to relax as her young pussy dampened with dew. I pressed the issue, splitting her pink lips with my tongue, licking the length of her slit from bottom to top, flicking over the bud of her clit, which brought forth a deep sigh. After ten minutes or so she forgot her anxiety and started to respond with a natural enthusiasm. When I inserted my tongue into her as far as I could extend it, she took my head in her hands while she bucked her hips up to me. I knew she was getting close to her first orgasm so I backed off a bit. I wanted to make this last, eventually teasing her to a full blown hurricane of pleasure. I brought her to the edge three or four times before finally pushing her over the brink with my upper lip grinding her clit while my tongue was buried deeply in her sweet vulva.

"Wow! That was fantastic," Amy puffed between gasps to catch her breath. I moved up her body and kissed her deeply with the taste of her pussy on my lips and tongue. I guessed this was probably her first taste of her own juices. I lay beside her caressing her tummy and the mound of her pubis, letting her bask in the experience, demanding nothing from her in return. She reached for my cock and told me she wanted to do the same for me but she didn't know how.

I took Amy's hand and placed it on my hard cock. "Wrap you fingers around me," I said.

Amy told me she had done hand jobs on her college boyfriend. "Is that what you want me to do?"

"Not just yet," I told her. "Right now I just want to feel your hand squeezing me. Feel how hard being with you has made me? That's what I get out of pleasing you. The taste of you was such a turn-on. Don't try to make me cum right away. Just play with me for awhile. Get familiar with how I respond to your touch. Discover for yourself what makes me feel good.

I kissed her some more while she held my cock firmly and gently stroked it. I moved my hand up to her breast and caressed a small nipple, bending my head down to take the other between my lips. "Do you like this?" I asked. "What does it make you feel."

"Kind of warm and maternal," she said. "I like it."

We lay together like that for a long time. I may have even dozed off for a couple of minutes when I felt Amy scoot down in the bed until her face was even with my cock. "How do I do this?" she asked.

"Start with some kisses," I suggested, "on the tip and up and down the shaft. You have to take your time. When you feel ready take a little in your mouth, careful not to scrape with your teeth. Get comfortable with me between your lips. You can suck a little, but not too hard. Stroke with your hand at the same time. Take it out of your mouth and rub it on your face and breasts. That's another way to keep me turned on. Handle my balls gently. Enjoy the sensations and don't worry about making me cum. Have fun feeling me respond."

Amy allowed her curiosity to lead the way. She gently caressed and kissed me to hardness. I caressed her face and played with her hair. She was getting comfortable and familiar with my cock. I let her play for a long time - until I couldn't take much more. Finally, I told her, "I need to cum now, Amy."

"How do I do this?" she asked. I don't think I'm ready to have you do it in my mouth."

I pushed Amy over on to her back then climbed astride her body with my cock in front of her face. I promised not to cum in her mouth. "I want to feel it in your mouth, but I'll pull out before I climax. When I do, stroke me with your hand. Squeeze tight while you do. I want to see my cum on your breasts."

I pushed my cock forward between Amy's lips. She opened for me. As I fed her my cock a little at a time, I told her to cover her teeth with her lips and take as much of me in her mouth as she could without gagging then to wrap her hand around the rest. I told he to use her hand to control the depth as I gently pumped into and out of her mouth. I built up a slow rhythm. "Look up at me, Amy. Keep looking into my eyes. Damn, you look so sexy with my cock in your mouth. You're going to make me cum soon. I love how you're doing this. It feels so good."

I neared the edge of the earth, watching Amy suck my cock. Before I fell off the cliff, I pulled out of her mouth and grabbed the hand that was holding my cock, squeezing it tighter around me. I thrust into her hand as I scooted down her body so that I was pointed at her tits. I let go a torrent of sperm, two, three four spurts on her flat her belly, over her milky white tits and up to her neck. "Keep stoking, Amy. Oh, that feels so good. You're making me cum so hard."

When I was fully depleted I leaned over Amy and kissed her long and hard. She sucked at my tongue. I broke the kiss and slid back down to the foot of the bed, spreading her legs and diving back between them with my face. I planted my lips firmly to the lips of her pussy. My tongue darted into her and my lip pressed into her clit. Amy's back arched. It didn't take long to bring her to an intense second orgasm. When it was over we lay snuggled together in the bed, me caressing the smooth skin of her back. She asked, "what's next?"

"I think we should both sleep for a bit," I said. "Stay the night with me. I can show you more in the morning." I took her hand and placed it on my flaccid cock. "This is your play thing, now. I expect you to treat it well."

We slept until morning. Amy woke to my gentle teasing of her nipples with my finger tips. Her nipples were small and rosy pink. They hardened to my touch but didn't get very large. It was a bit of a disappointment to me. I was accustomed to my ex with her large double d tits and sensitive nipples that hardened into bullets. Amy's seemed less sensitive and she didn't seem as turned on by nipple play. Still, she got the message and reached for my cock, already half way to harness and yearning for attention. After a few minutes of play, I rolled onto my back and pulled Amy on top of me. "I want you to lay on top with the lips of your vagina on my cock," I told her. "I want you make yourself wet by rubbing up and down the length of my cock with the lips of your pussy." She seemed hesitant. "It's okay," I said. "There won't be any entry. You're just going to pleasure both of us with contact between your clit and my penis. It's called a pussy job and you'll be in complete control."

Amy got the idea and was soon sliding her labia up and down the length of my rigid cock. I could feel her wetness growing as she slid herself against me. Soon she was panting and stoking me with a regular rhythm. She gradually increased the speed according to the needs of her own pleasure, varying the rhythm. Tiny whines and moans escaped from her lips as she drove herself toward a shattering orgasm. She collapsed on top of me with a final squeal and ground her hips side to side over me in apparent ecstasy.

When she stopped shaking, I rolled Amy off of me. We lay side by side as she recovered. I turned and kissed her. "Good?"

"Fantastic," she said. "I want to do you now."

"Okay," I told her. "I want you to curl up with your head on my tummy. Don't touch me yet. I just want you to watch my cock. Watch until it goes completely soft and when it's small I want you to take it in your mouth, the whole thing. You should be able to do that. I want to feel it grow in your mouth. As it does, you can back off as you need to, but keep as much of me in your mouth as you can for as long as you can."

Amy scooted down in the bed and curled up as I suggested. We lay still except for me again, caressing the tender skin from her shoulders to her lower back. I felt her lurch a couple of times as my attention came close to a tickle. It took quite awhile for my cock to go soft. That was mostly due to my anticipation at having my entire organ in Amy's mouth, a dick that was now well seasoned with the juices of Amy's sweet pussy.

Finally, I was ready and I gave Amy a little nudge. She dutifully open her sexy mouth and took my cock completely in. It started to swell immediately and Amy did her best to hold me as deeply in her as she could. By the time I had reached full hardness, Amy had about half of me in mouth. I rolled us over so that we were on our sides facing each other. I began sawing my engorged cock into and out of her mouth, pausing from time to time to savor the pleasure she was giving me. As I neared my own orgasm, I gripped my cock so I could thrust more forcefully without choking Amy. At the last moment I pulled out and shot a load of cum onto Amy's neck and cheeks. After the last thick stream of jizz left me I shoved my cock back into her mouth, leaking that last few drops onto her tongue. I felt her swallow. I rubbed the tip of my cock through a pool of sperm on Amy's cheek then touched it to her lips. She responded by opening her mouth so I could make another deposit. Again I watched her swallow. I gathered more sperm with the tip of a finger and dabbed it on Amy's lower lip then watched as she swept it into her mouth with her tongue. It was the sexiest thing I had ever seen. So much for her fear of cum in her mouth. I finished up by rubbing the cum on her tits into her translucent skin as if it were a moisturizing lotion.

Over the next few weeks, Amy and spent our weekends together. It wasn't all sex. We talked, went for walks and often cooked together. We listen to music, mostly classical, with the lights off, often with Amy kissing, caressing and gently sucking my cock as if it were an object of worship. We'd end up in bed getting each other off by any means we could think of. My only regret was that I couldn't really tit fuck with her because her breasts were too small. I once coated her small tits with baby oil and had her drag them up and down the length of my cock. It felt nice but I couldn't come that way. Mostly we just ended up making a mess. Several times I lubed my cock with oil and fucked Amy's thighs from behind her. I did cum that way, but really I longed to fuck Amy's cunt. I didn't put any pressure on her though. I didn't want to be that guy.

As we talked, I learned much about Amy's upbringing and her past, what little of it there was. She went all through high school, having had only a couple of dates. She was just too shy as a teen, could hardly talk to a boy. She had never masturbated, wasn't sure how or even why someone would to that. Our first night together was her first orgasm ever. She was completely knocked out by it and didn't stop thinking about it for days afterward. She had read or heard about it and knew what it was but the actual experience shocked her. In college, Amy finally had her first boyfriend. It was a small religious school that produced teachers. The boy, Nick, was nearly as repressed as Amy was. Sex was limited to him feeling her up her tits while she gave him hand jobs in the front seat of his car, usually at a drive-in movie. They cleaned up with napkins from the concession stand.

It was January and the city experienced a huge blizzard. I ran to the grocery to stock up on what I could but there was little left on the shelves by the time I got there. I barely made it Amy's apartment through the deep and drifting snow. We both were relieved that we wouldn't be snowed in alone. One thing I did find at the store was a package of condoms. It was almost the last one. A lot of couples were expecting to be snowed in. I didn't mention it to Amy.

The storm lasted three days. On the second night we were together, and just after I had brought Amy almost to tears with my tongue, she said, "I'm ready for you. I want to do it. I want to give you my virginity."

"Are you sure?" I asked her. "I will if you want to but only if you're really sure."

"I'm sure," she said. I've been thinking about it for weeks. I want you inside me."

"Of course I want it too," I responded but I have to be sure. What if we sleep on it tonight and if you still want to, we'll do it tomorrow night. Think about how you're likely to feel about it a week or a month after and how it'll be for you if we do or if we don't end up together."

Amy put out her lower lip to express disappointment. I laughed at her and took the lip between my teeth, growling like a bear as I bit down. "OUCH!" she feigned pain from the gentle nip. "No biting."

"Meanwhile, you can give me one of those perfect hand jobs," I said. "Let me cum on your lips so I can watch you lick it off."

That brings us back to the opening of the story, the third day of the storm. Amy and I spent the day together doing non-sex things and looking at each other not sure of what to say. She finally asked, "do we really have to wait for tonight?"

"Not if you're still sure," I said.

The wind from the storm made the old building drafty and cold. I suggested we start in the shower to get warm before we slid under the covers of the bed. We had a long shower and played a lot of sexy touching and teasing games. Once in bedroom I asked Amy about the issue of birth control. I was relieved when she told me that her period was due tomorrow of the next day (she was very regular). At least I wouldn't have to explain the condoms I'd bought at the store. It also meant I would be able to cum inside her, making my first time with her that much more satisfying.

We started slowly, petting, teasing and kissing until Amy was soaking wet and I was rock hard. I put Amy on her back and brought her to a first orgasm by eating her out. I was sure to leave behind a lot of saliva mixed with her natural lubrication. After resting awhile I set Amy to sucking my cock, leaving me good and wet to provide even more lubrication. Then I positioned myself between her legs and massaged her slit with the tip of my penis, eventually spreading her lips and inserting just the very tip of my cock. I had never done this before, so I was only guessing at the proper way to approach taking a woman's virginity. My toying seemed to please her and I pushed in a little, stopping to measure her reaction. She gave me a nod.

I had worked my cock half way into her virgin pussy when she cried out, "it hurts, it hurts!" I asked her if I should stop. "No," she said. "Give me a minute. I want to do this." I held still, caressed her pretty face and waited for the pain to subside. "Okay," she told me. "Keep going." I carefully pressed on, sliding in another inch. Amy took in a sharp breath through clenched teeth. "Oooh".

I pressed forward again, overcoming the last of her hymen's resistance until I was completely inside her. She continued breathing through pursed lips. I let her rest again. "That's it," I told her. "You're not a virgin any more." I kissed a single tear from her cheek.

I withdrew just an inch or so, pushed back into to the hilt, then out again, being as careful and gentle as I could. From Amy's reaction I could tell the pain had lessened. I kept up my motion, gradually speeding up until my in and out motions seemed not to be causing further pain. It didn't take me long to spill a pint of cum deep inside her. When I finished I lay still until my cock shriveled and slid out of her pussy on it's own. The thin film of virgin blood on it is something I'll never forget. I had rarely felt more satisfaction and I told her so. I asked how it had felt to her.

"The pain never went completely away but it wasn't so bad once you were all the way in. I've heard the first time isn't that great. What I'm really looking forward to is when it's normal, but you have to promise me two things."

"I can't refuse you anything right now, Amy. What two things?"

"No matter how much we both like having the regular kind of sex, you won't stop using your tongue on me and you'll still want me to use my mouth on you. I love both of those things. I think you've made me an addict."

I quickly agreed.

Amy and I didn't end up together. She was the kind of girl who belonged in the country or in a small town. That wasn't the life for me. That eventually became clear to both of us and we parted company after just over a year, when Amy's contract expired and she didn't renew it, realizing she didn't want to stay in the city. She ultimately did go back to Iowa. We didn't communicate after that. Forty years later, I found Amy on Facebook. That's what prompted me to write our story. I didn't try to message or friend her. I just wanted to see how life treated the only woman who ever gave me the gift of her maidenhead. Amy married. The husband wasn't a farmer but he owned an insurance company that sold crop insurance. They had just one child, a daughter who looked as though she had stepped out of a Norman Rockwell painting.

A friend once told me that a woman never forgets the man who took her virginity. I always hoped that was true and I know for sure it's true for the man, at least it has been for me. Amy will never know the number of times I masturbated to the memory of that look on her face when my cock hit bottom inside her that first time. I like to think she has pictured that third day of a blizzard at some random hour while she's washing dishes, listening to her favorite Dimiti Shostakovich , or teaching the children in her class the definitions for a noun and a verb - all with no regret.