Gentle First Time Anal
287. Woman's Story: I Was Sore the Next Day (10/11/04)
The first time I ever had sex I was 17. My boyfriend, who I'd been with for 7 months at that time, was 18. He and I had talked about having sex, but he never pushed me. One night, he came to my window. I was surprised, and I let him in my room and laid in my bed with him. It was probably 12:30 at night. He'd said he'd been thinking about me all day, and I the same for him.
He started to kiss me, and I pushed my body close to his. He started to play with the elastic on my pajama shorts, and asked me if it was okay. I said, yes, of course. He slowly slid my shorts off...and started to finger me. I moaned and sighed with pleasure, trying not to wake up my sister across the hall.
He asked me if he could taste me. He slowly went down to my wet pussy, licking and flicking my clit with his tongue. This was the first time I'd ever been eaten out. I put a pillow over my face and moaned when I'd reached an orgasm.
He came back up to me, taking my shirt off and sucking my nipples. He put his hand in between my legs, and I spread them. His cock was throbbing. He teased my clit with it, and then finally stuck it in me. I rocked my body with his, as he pinched my nipples and kissed me.
He pulled out of me and came on my stomach. He cleaned it off like a gentlemen, and I sucked him hard again. After this, he turned me on my side and started to finger me again. He was ready for round two. I stayed laying sideways as he fucked me slowly at first and then faster and faster. The next day I was sore and bleeding, but it was well worth it.
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236. Man's Story: On the Table (7/8/04)
The best time I ever had sex was definitely my first. I was with my girlfriend on a date to see Alien. Nice long movie to get turned on by, and it was a horror, so I could start by holding her hand. I figured it wouldn't be good for IN the movie theater, but, you know...We went home, and we fucked each other. Hard.
Anyway, everything went as planned. We made out in the parking lot for a few minutes, we watched the movie, I held her hand, and at least I got turned on in anxiety. When I drove home I asked if she wanted to have sex. She agreed, but it was her first time so she was nervous. (My first time too, but I was just excited.)
Once we went in my apartment we started to just rip off each other's clothes. She was nervous about fucking so she just started sucking my cock. It was SOOOO good... I started to rub her tits then went to rubbing her clit as hard as I could. Her eyes bulged so much and she stopped sucking my cock and shoved me onto the table. I lay on my back on that table just as I came. Some dripped down and she got on top of me. She pushed my cock into her pussy and screamed.
After that I was rolling and stroking while she was kicking and biting and finally I dumped my load in her. I felt the pleasure subside but I knew it would come again. We only fucked each other for like five minutes but I came three times in the end.
217. Man's Story: Shopping for Condoms (5/1/04)
My girlfriend and I were at the grocery store shopping for stuff to make dinner. We hadn't had full-on sex yet at that point, just stroking and messing around with our clothes on. At one point I was standing in the aisle staring at the condom display, and getting kind of horny. My girlfriend looked over and saw me looking at the condoms. I was busted! But then she came over and laughed at me and said, what kind do you want to get? I was embarrassed, but I smiled and grabbed a packet of Trojans and tossed them in the cart. I'm sure the clerk who rang us up knew what would happen later. When we got back to her place, we actually made dinner and ate it, although my mind was on other things. Eventually we started fooling around and ended up on her bed, half-undressed. She gave me a long kiss, then got up and went to the kitchen and came back with the box of condoms. She asked if she could put one on me. I almost blew my load when her hands touched my cock. We had sex most of that night and fucked our way through the whole box in under two weeks (it was a dozen).
215. Man's Story: First Time Fingering (4/23/04)
The first time I ever fingered and gave oral to my girlfriend was at a church camp. It was the first night of camp and we snuck off in the woods for a little private time. We stopped at a grouping of picnic tables and sat down on one of the tables. It was dark out and the moonlight was all there was to see by. According to the rules for the week members of the opposite sex were to be in groups of 4 or more if they were to be unsupervised...oops. Well, we started making out, and I started rubbing her pussy from the outside of her little blue cotton shorts. I could feel her getting wet, and I didn't want her to go back to the cabin with a big wet spot on her crotch, so I slid my hand inside her shorts. She told me to stop, but then I explained to her what I was doing and she let me go on. Well, I accidentally slipped my hand inside her panties instead and she let out a gasp. I felt bad, so I started to remove my hand; then she grabbed it and held it there. I slid a finger inside her and it felt so good. Then after fingering her I slid down and licked her pussy until she was about to scream. We stopped for fear of being spotted, and I fell asleep that night sniffing my finger that still smelled like her wonderful juices.
202. Man's Story: Johnny Cum Lately (1/18/04)
I was a Johnny-come-lately, so to speak, to the sexual world. I was 18 years old, as was the girl I was seeing. We had fooled around a lot, but had never done the deed. She was a virgin who wanted to wait for marriage, and I was a virgin who didn't. One night about three months after we started dating, I got her real horny. I was dying to stick my dick in her tight little pussy, but I held off. We had somehow ended up on the floor. I was sucking on her tits and kissing her all over. I asked her if she wanted me to stop. She shook her head "no". So I helped her onto the couch and knelt down in front of her, maneuvering my stiff cock to her wet hole. As I pushed in, she stopped me. "It hurts," she said. I told her it would, and not to worry, I'd be gentle. I pushed in again, feeling my dick stop against her inner wall. I pushed again, and again, but since this was also my first time, I nutted after about 30 seconds. Although it hurt her a lot, we kept having sex after that. It hurt her the next two times, but then got better for her. I can now last longer too!
186. Man's Story: Help With Homework (11/13/03)
I was 16 at the time and had only really been interested in sports. Rachel was the same age and good at math, so that evening when my parents were away at a concert, she came round to my house to help with the homework. Sitting on the bed, she spotted a soft porn mag of my father's that I had rescued from the bin. "Do you enjoy wanking?" she asked. I was shy but had to admit that I did, whereupon she asked if she could watch me do it. Surprising myself, I got my cock out, laid on the bed, and started stroking it. She watched with interest and was soon to see wads of come spurting from my dick. She carefully cleaned me up with some tissues and asked if she could touch my now sagging dick.
I had never been with a girl before and the excitement was incredible. She started to stroke me as I had done before, and within a couple of minutes I was spurting more come all over my belly. Once again she obliged with the tissues and asked if I would like to touch her. How could I refuse? She pulled her short skirt up to her waist and opened her legs, exposing her white panties. She put my hand on her crotch. I was surprised because she was very wet and I thought she had peed herself. She was obviously enjoying it with the noises she was making. After a few minutes she asked me if I wanted to do it. She removed her panties and lay on the bed with her legs wide open. She told me to climb on top and do what I read in the magazine.
Getting on top was easy, but I couldn't find her cunt with my cock. After considerable squirming and help from her hand, I was inside her. The feeling was exquisite and I couldn't help but thrust away quickly. I came again within seconds of entering her. All I wanted to do now was sleep, but she undid her blouse and lifted her tits from out of her bra and put my hands on them. Till then I had been shrinking inside her but now things were starting to happen again. My cock was hard again and I started to slowly move inside her. This time I took things a bit more slowly and probably managed to fuck her for about five minutes before coming again. It was only after she had left that I realized that this had not been her first time.
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170. Woman's Story: One-on-One
It was a Thursday afternoon, which meant game day at our high school. I was on the girls basketball team so I helped set up for the boys game. I went into the gym to find my ex-boyfriend shooting around. He looked at me and I looked at him and we both just smiled. I looked over to see the economics teacher Mr. Tanke deeply reading his news paper. I paid him no mind and went on to talk to Leron. As we went on talking, somehow the subject of sex came up (mind you that all of the time we were together we never fucked) and he suggested that we go into the locker room. Being the stubborn person that I am I asked why. He shook his head in anguish as if he were mad at me, and I hate that, so I said sure. He looked pretty surprised but wasn't completely shocked. He took my hand and led me into the locker room to find it completely empty. He took me to the back portion which was called the cage. He threw me against the wall and we began to kiss deeply and passionately. Before I knew it I felt his hard dick in his warm up suit and I couldn't help but to drop to my knees and suck his sweet long cock. It felt and tasted so good in my mouth that I wanted to swallow it all, and before I knew it he exploded in my mouth. It tasted so great he was surprised to see that a 18-year-old could suck so well. He then feel to his knees and pushed me onto the floor and ate my sweet little pussy vigorously. I had no choice but to cum in his mouth. I was still wet and he was hard again. We fucked hard for about fifteen minutes or so before we both came. I guess all the noise we were making attracted attention cause before we knew it one of his team mates walked in. We looked up from the floor and laughed. He laughed too and said it's game time. Leron said, OK, just give me a minute. We quickly dressed and left out of different exits of the locker room. It was the best one-on-one ever. No winner, no loser, just both opponents satisfied.
168. Woman's Story: Summer Break
The summer before I came to college, I went on a two- week trip to Mexico. My high school group met up with ones from Indiana and Florida. I was hot for a guy from Indiana named Rick. I'm not sure why, he wasn't my type at all. He was cute in that Superman/Clark Kent way, and he never said much. Well, the last night of the trip I got drunk at a disco in Puerto Vallarta. My friend Nikki, who had a thing for a different Indiana guy, was with me and we motivated each other to go try to hook up with them. I did the sluttiest thing ever and walked up to Rick with my room key and said, "If you come with me now, you're going to get laid." He accepted the offer. The minute we got back to the room we started taking our clothes off. I started by sucking him off. He had the biggest dick I've ever seen, long and fat. I got a little scared. He started to finger me and I was dripping pussy juice all over his hand. I laid down on the bed and spread my legs. I figured we would just go straight to fucking, but instead he licked me softly and nibbled my clit. I was grabbing handfuls of his hair and groaning. I wanted him to fuck me so bad. He was getting off on it to. I was basically begging for him to give it to me. Finally he stopped eating me and slipped his dick in. I felt something rip but I wasn't about to stop him. We fucked like animals all over the bed, we did positions I had never done before (hey, I was just out of high school). when it was over we lay there sweating and panting. I realized that huge cock had torn me open and I was starting to get sore. Since it was the last night of the trip, the next morning we said goodbye and went to our separate groups. I had trouble walking for days.
165. Woman's Story: First, Best, Hardest
I was at my boyfriend's house and we were talking about love. He said he loved me and that he thought the time was right. I had thought that for a long time already. I was wearing a low-cut spandex shirt and a mini skirt, that's all. No underwear. I quickly agreed and jumped onto the bed. We were both virgins. He started by pulling off my shirt, squeezing my nipples and licking all over my round, full tits. He was driving me crazy. I unzipped his pants and took out his thick, big, hard cock. God, he must have had 8 inches. I started stroking it, and in about a minute he came without even touching my cunt. I groaned, "You're a sure thing, aren't you?" I slipped his huge prick into my pussy, and got on top. I rode him until he flipped me over and slammed into me. He howled, "I'm gonna fuck you harder than you ever will be again, you little whore." And he did. I had to muffle my screams with a pillow. He got me off many times that night, more than any other guy ever could. He finished by again sucking my huge, firm tits. We are still having sex, 6 years later, and I've never had better than him.
5. Woman's Story: First Time Blow Job
Joey was a few years older than me. He was so cute and strong, and I admired him and thought he was really exciting.
When he invited me over to his house one day, I enthusiastically walked to the bus and got there as soon as I could. His mother was home and he introduced us.
"Let's go to my room," he said, and his mother looked at me approvingly.
We sat on his bed for a few minutes, talking about school. Then he asked me if he could teach me something that I hadn't learned in class -- how to get a boy off. I giggled and agreed, hoping his mother wouldn't know. I heard her doing the dishes while Joey unbuttoned his Levi's (I remember those so clearly -- and he wasn't wearing underwear). He took off his pants and held his cock in his hand, which looked massive to me.
He told me to grab it. Then he told me to suck on it, so I bent down, my face cautiously moving toward him.
He smelled clean and the skin of his cock was smooth. I was warm and comfortable and pleased with myself that I was learning this great lesson about sex. I wrapped my mouth around and ventured to suck, like he had asked.
"Just slide your mouth up and down," he suggested, and I did. He pushed my head down, encouraging me. Then his hand covered my hand (which was wrapped around the base of his cock still) and he made motion for me to stroke him. It was difficult to coordinate with the sucking, but it didn't take long before he started shaking and making soft moaning noises. He pulled away from me quickly, and I watched his cock spray cum on his bed in front of me.
79. Woman's Story: First Time's the Charm
It was my first time doing anything with a guy. I was so nervous. The guy I was with was also a lot more experienced than I.
I snuck out of my house at about 1:00 am. From there we met at his car a little ways down the street and drove off to his house. When we got to his house he put on some music and we relaxed. Soon things starting heating up and I started sucking on his fingers. He seemed to enjoy it, so because I was in a risk-taking mood I asked if he would like me to suck somewhere else.
He un-zipped his pants and his cock popped out. Slowly I started licking and sucking getting harder and faster and repeating everything he said he liked. I continued this for about 5 minutes until he pulled me away and took of my shorts and panties and started fingering me. It was amazing...and before we knew it we were sixty-nining and enjoying the hell out of it. He was so incredibly good I didn't want to stop. I must have come about twice when finally we decided to stop. We laid on his bed talking for a bit then he took me home. I cannot wait till we do this again. thinking about this makes me so horny. This definitely was not bad for a first time.
74. Woman's Story: Her First Time
In high school I felt like the only virgin around. All my friends were doing it, and while I went out with guys all the time, I never met anyone who I really wanted to fuck. I wanted my first time to be special, and all the guys I dated were just too lame.
Still, I was horny as hell. I masturbated all the time, in the morning, after school, at night, I even locked myself in a plane bathroom and fingered myself. I became obsessed with cumming, it just felt so good. I would go online read a nasty story, get all wet, and then lie on my stomach on my bed, and hump my right hand...Still, there was something missing...namely a cock.
My parents sent my best friend and I on a graduation trip and I vowed to myself I was going to get my cherry popped. After a couple days of sitting on the beach and checking everyone out through my sunglasses, I saw this really really hot guy...Well, it didn't take long for us to get to his hotel room.
We started out slow, he carefully undid my bikini top, and touched my boobs... we kissed gently and pulled at each other. I got hotter than I ever have with a guy and began to feel my pussy get wet and tense. I moved closer to him, unlaced his trunks and saw my first real penis. Oh my god it was beautiful, it sprung up to meet me. I really couldn't believe how big and hard it was. I am used to sticking my finger in my pussy...and not even that, I usually just play with my clit until I cum. So, needless to say, I was a little worried.
Nick (that's his name) was really sweet...he sucked me all over, my breasts, my neck, my stomach, my clit...his lips made me so hot and horny. I touched his penis and wanted to suck it, but realized I really just wanted it in my pussy, I mean I can give head whenever. Nick sat on the bed and I tried to lower myself onto his cock, but it was so big...I could get it half way in, but it hurt, and I wanted him to be able to really fuck me...I wanted to feel his weight on me. We rotated and he mounted me, at first he just placed his hard cock near my pussy and made me move my hips searching for it...then he slowly pressed it into me. It was so warm and hard I really felt the best connection with him. It hurt like hell, but then again I was being fucked so I can't really complain.
After about 8 strokes of him entering my vagina, we really got into a rhythm. I stopped having to cringe with pain and began to pant, he was making me so hot. Nick pumped my pussy and I began to yell, "fuck me, fuck me, fuck my wet pussy...yeah yeah fuck me." I don't even know where it came from...But yelling make it so much better. He did fuck me, and while I have nothing to compare it to, it was so much better than fingering myself. As his cock slid in and out of me and my pussy got tighter around it, his cock got bigger and exploded so much cum into me...The best thing was, he kept pumping a little, as if he was trying to really jam the cum in me...It was the best feeling in the world. I cannot wait to be fucked again!!!!!!
61. Man's Story: First Love
One of my male friends from high school had a sister who was kind of cute so I asked her out on a date. I think we went to a movie and went parking afterwards. We were kissing and petting through our clothes and we started opening but not removing clothes because it was cool outside. I was fingering her cunt and she was rubbing my now hard dick. I paused for a moment and the next thing I know she has her mouth on my dick and it is feeling great. I was so surprised that she did this, on the first date even. So we went out whenever we could and every time I got a great blow job. She was 14 or 15 at the time. One night she was babysitting and she invited me over. I came over and she said we could go up to the bedroom. We stripped and she guided my hard dick into her pussy. The look on her face as my dick slid in was priceless. I will never forget it. Never.
14. Woman's Story: Vibrator first time
The first time I went shopping for a vibrator, my friend and
I stopped by Good Vibrations in San Francisco. They have a great selection
and wonderfully enthusiastic employees, who suggested I try out one of the
vibrators in their "dressing room." It was explained to me that I need to
keep my underwear on, but that I can try out how it feels. I brought one
into the private room, dropped my pants and turned on the vibrator. It had
a healthy buzz, despite the fact that it was a small device -- "perfect
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