2:49 p.m. :: 2002-03-15
My First Time
My girlfriend encouraged me to post this about my first time because she is interested to know what it was like for me. It was a long time ago and some of the events have probably become a bit clouded by sentiment but the important facts still remain intact.
It was school holidays at the end of January 81. I was spending a week with a school friend, Ally, and her family at their farm in the country. I was an only child and had led a fairly shelered existance up until then. I think my parents thought that it would be good for me to spend some time with other kids, hence the holiday. Ally was also 14 and had two older brothers Chris who was 18 and James who was 16. January is summer in Australia an it had been really hot all week. On the second last day of our stay Ally, James and I decided to go for a bush walk in the morning before it got too hot. After about 2 hours we were completely lost and it was getting really hot. James took off his shirt to keep cool and Ally complained that we couldn't take our shirts off too. James said there wasn't any reason why we shouldn't because there was no one around to see us. I remember being hesitant but Ally had her shirt off in no time. I took my shirt off too and we proceeded to try to find our way home. Ally and I had both started puberty early and we were well enowed by that stage. James, who had been walking out in front, soon dropped back and was walking next to us. He was paying a lot of attention to our breasts. I probably would have been a C cup and I guess Ally was about the same. I remember feeling very selfconscious as it was the first time a guy had seen me topless but I also felt sexy walking along half naked in the bush.
After about an hour we worked out where we were and started to head back to the house. Our route took us past a water hole and Ally suggested we go skinny dipping to cool off. James said OK but I wasn't too sure. When we got to the water hole James and Ally just stripped off and jumped in the water. I have a vivid memory of his flaccid penis as it was the first one I had ever seen. All the girls at school talked about how big they were but James' looked so small. I was nervous as I removed my shoes and socks then my shorts. They were watching me from the water and I really didn't want to take my panties off. Ally kept sayin it felt really good swimming in the nude so I finaly worked up the courage to drop my panties. I jumped into the water immediately so James wouldn't have time to see me. I remember nearly fainting as the cold water took my breath away. Once I was in the water we splashed about for ages and had a 3 way water fight and tried dunking each other. There was quite a lot of physical contact but I don't remember it being particularly sexual in nature until James grabbed me from behind to try to drag me under. It probably wasn't intentional but his erect penis ended up right in between my arse cheeks. He almost entered my anus and then slid across my vulva. I reached between my legs and grabbed his erection so I could push myself away, finally making it to the surface shocked and spluttering. I was surprised to see James blushing and he apologised repeatedly.
It took about 5 minutes for what had happened to sink in then it hit me. I think that moment was my first real feeling of sexual desire. I was often horny and masturbated regularly but I had never really felt that I wanted to have sex. At that moment I wished there was just James and I there so we could climb out on to the bank and I could explore his body intimately. We swam about for a few more minutes before climbing out on to the bank to dry off. I was amazed that James was still fully erect. He seemed very un-selfconscious until Ally made a joke about his hard on and he blushed again. I was still nervous about being naked in front of James but was relaxed enough to lie down next to him in the sun. It was Ally who suggested we play truth or dare as we lay there. There was lots of silly truth stuff about kissing boys and kissing girls and masturbating to start with. Ally eventually accepted a dare from James. He dared us to kiss for a count of 30. Ally and I had practiced French kissing with each other many times so it wasn't a big deal. All the truth sex talk had got me horny so that when Ally rolled over and kissed me I literally saw stars. When James had stopped counting neither of us wanted to stop. Ally had next go and she dared me to masturbate while she and James watched. I couldn't say no to the dare and I was so aroused now that I wouldn't have said no anyway.
I spread my legs and James knelt in between them so he could see. Ally and I had watched each other masturbate before so she wasn't very interested in what was going on down below. I basically just did my normal routine. I starting with rubbing my breasts and pinching my mipples then worked my hand down between my legs to play with my clit. I could see James' penis was fully erect now and it looked pretty impresive. I imagined what it would feel like to have it thrusting inside me and that was all it took to set me off. I came quite loudly and was embarased about it. James just said wow and then lay back down beside me. Ally whispered in my ear that I should dare James to masturbate. He accepted and began to stroke himself, slowly at first the much faster. Ally rested her head on my shoulder so she could see what James was doing and started to casually stoke my nipples. After a couple of seconds she asked me to finger her and I obliged by sliding my hand around her soft bum and sticking two fingers into her vagina. Ally's vagina was wet and tight and she squeezed my probing fingers with their every thrust into her body. James' penis looked absolutly huge now and was coated with slick precome. I was intrigued by how fast his hand was moving up and down his thick shaft. He let out a long moan then great fountains of semen shot repeatedly from his penis splattering all three of us. I was awe struck.
Ally was the only one who hadn't come and James wasted no time in daring her to masturbate while we watched. Ally asked if I could suck her nipples while she masturbated and James agreed. I removed my fingers from inside her and she rolled on to her back spreading her legs wide so James could get a good look from between her knees. Ally began to masturbate immediately and I sucked and gently bit her hard nipples. I desperately wanted to come again so I stuck two fingers into my vagina from behind and began to pump them in and out. James was kneeling now and stroking his hardening penis while he watched his sister and I going for it. Ally must have been really turned on because she came violently, bucking and swearing. That set me off and I came for the second time.
We all lay back down and spent a minute or two recovering. James lay there slowly stroking his erection again. Ally eventually leaned over and asked me, "Truth or dare". I was puzzled because I didn't think there was mush else I could be dared to do. Why I said dare, I still to this day don't know. Ally said, "You have accepted a dare and now you have to go through with it." "What is it?", I asked. "I dare you to fuck James!" I don't know who was more shocked, James or myself. I tried to talk my way out of it but Ally wouldn't budge. To be honest I really wanted to have sex with James there and then but I wasn't sure that I wanted Ally to watch. In the end the sexy goings on of the last couple of hours and my desire got the better of me and I agreed. All I said was, "I want to be on top."
I had fantasized about what sex would be like but I had never imagined it would be on a rock beside a water hole. I knelt facing James straddling his erection and reached between my legs to hold his penis. It was much harder than I thought it would be and was still coated with his earlier ejaculation. Ally moved around behind me and said, "Tell me exactly what it feels like." This is the clearest memory I have of that day. With my free hand I spread open the lips of my vulva and slowly lowered myself down towards James' penis. I couldn't bring myself to look and relied on my hands to get us into alignment. The tip first touched somewhere between my clit and vagina. A quick adjustment and the head of James' penis was inside me. I stopped there for just a second or two before my shaking legs gave way and I sank down on to James lap, his erection buried deep inside me. To this day I try to get the exact same feeling of that first penetration but without success. Ally said, "Oh.......God." And then, "What does it feel like?" All I could manage was, "Big and Hard." I thought it was really going to hurt but aside from being streatched both lengthways and widthways it wasn't too bad at all. James had a grimace on his face and I asked him, "Are you OK?" "Don't move because I'm trying not to come," he replied. After a few minutes of just sitting there locked together, James put his hands on my hips and urged me gently to start moving. Slowly at first, then building speed, I moved up and down on him. His hands went to my breasts and he squeezed and rubbed them firmly. Ally, sitting behind me said, "My God Kate, your pussy is huge. Oh fuck, it looks great" The pleasure was so intense I came immediately. I screamed, "Oh, FUCK" It was only one or two pumps more and James grabbed my hips and pushed me down hard on his crotch. I hadn't even thought about his orgasm but now it was happening right inside me. I could feel every pump of his ejaculation right in my very core. Completely drained, I collapse on to James' chest. Our lips met and we just started kissing and didn't stop. Ally was saying something behind me but I didn't hear what it was. We just lay there, his penis still hard inside me, kissing.
Ally jumped back into the water and after an age we broke our embrace and joined her. I tried to wash as much semen out of myself as possible but didn't have much success. Finally we dried off, dressed and headed back home. James and I walked along hand in hand. That was actually a really special moment as I felt very close to him. I was pleased that he accepted and liked me even with my clothes on. That night after everyone had gone to sleep I creept into James' room and we spent the rest of the night together making love. We eventually fell asleep curled up together with him inside me. The next morning James' mother woke us for breakfast. "Did you two have fun last night?", she asked. I was amazed that she wasn't angry. Later that day she took me aside and told me she thought I was probably a bit young to be having sex and that I should wait until I was more responsible. I guess in hindsight I'm very lucky I didn't get pregnant. James and I dated for nearly two years but we didn't ever have sex again. A shame really. Funnily enough, I didn't have sex with a guy again until I was nearly 20 and in my first year of university. I did have sex with a lot of girls though!
There you go, that was my first time. Sorry if it was a bit long winded.
Did you miss...?
Casual, Random Sex - April 22, 2009
For Your Eyes Only - 2008-05-29
Amanda - 2008-05-29
Faithful Wife - 2008-05-17
Nasty Mother In Law - 2008-05-17
Orchids
post yours
fresh
spent
profile
notes
contact
about
links
diaryland
