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My First Real Girlfriend

Posted by: Age: 17 Posted on: 3 comments
5 likes 4860 views Category: Masturbation Male-Female Tags: wanking, fingering, panties
How our sexual activity developed

Tony and I lived in the same village and went to the local boys secondary school, he was a year older than me and we were casual friends. We also both went to the Friday youth club and one week he told me that his sister, Olly (Olwyn), was joining as she had just finished some exams. She was 16, about 6 months younger than me and although I had seen her around the village we had never actually spoken. She was lovely, had a fantastic smile, soft voice and a trim figure, over the next few weeks we both went to the youth club and became good friends. When I thought of her it made me horny and she was on my mind most times when I wanked off which was quite often.........Eventually I asked her out, we went to see a film and cuddled and kissed in the cinema but nothing else. I think it was on our third date, I had my arm round her as we sat together, my hand was hovering over her boobs and when she snuggled closer it sort of ended up on them but she just kissed my cheek and didn't move it when I cupped them. Wow my dick was so hard! Once at a party I had groped a girls boobs over her clothes but this was the first occasion I had taken my time and really enjoyed it. About a week later after school, we were alone in her house watching tv, we cuddled together and I cupped her boobs over her clothes, she kissed me and undid her blouse and bra which she pushed up so I could see her boobs. Not big but so pert with small pink nipples, I felt their softness and then kissed them, she seemed happy with this and I was so horny my dick seemed as though it was going to explode, I took her hand and just laid it on my lap so she couldn't but help feel it, she squeezed it so gently but just the once then moved it away but she did still snuggle close and I kissed and caressed her boobs for about ten minutes before she said her parents would soon be back so she needed to get herself sorted. I didn't stay long once they arrived as I had to get home for my tea and homework but she gave me a nice kiss when I left and as soon as I got home I went to my room and wanked off without the need for any porn. Tony was happy with me dating his sister although obviously neither she nor I ever mentioned anything about sex to him, the only time he ever mentioned it to me was once early on when he just said "not to fuck about with her" or he would kill me. A couple of weeks later one of the guys at the youth club had a birthday party at his house, I went with Olly, Tony at that time was seeing another girl from the club and they also went. His parents left us alone for a couple of hours and as it happened one of my friends went to go upstairs to the toilet and had interrupted Tony finger-fucking this girl in the hallway, Tony knew that I knew about this so I felt a little better that he could not act the innocent big-brother about anything Olly and I were both happy doing. We liked each others company as friends, she was feminine but would take part in stuff at the youth club as one of my friends rather than as a girl, I mean like playing snooker or even joining in a football kick-around, my friends liked her and she really fitted in well but when they swore using the word "cunt" she would tell them off which I quite liked as it showed she had spirit. I would walk her home after youth club and also we tried to meet up one other time during the week, I really looked forward to this as we always found time for a cuddle and goodnight kiss and she was quite happy for me to caress and kiss her boobs. On more than one occasion walking back to my house I have had to stop by a garage block and wank off in the darkness. Shortly after my 17th birthday I passed my driving test and was lucky enough to be able to use my aunts small car, she lived in the village and never used her car except for travel to and from work so it was always available in the evenings and at weekends. I had a Saturday job and the first week after passing my test I picked Olly up in the car and we went for a drive into the countryside and parked up in a secluded layby. We kissed and cuddled and I undid her blouse and she said she would take her bra right off which sounded so hot to me as I had never seen her boobs like totally naked, her bra had always been undone but pushed up. I had wanked off in the shower after work and also first thing that morning but I was still feeling horny.......... Olly was trying to get her bra off whilst still in the car so I said she might find it easier outside and we could get in the back seat which she agreed. She put her blouse back on but left it undone. I saw how lovely her boobs were and gently sucked her nipples which she obviously liked as she was stroking my hair and pushing towards me rather than pulling away. My dick was so hard and rather embarrassingly was in a rather uncomfortable position as I was leaning into Olly so I told her sorry but I had to adjust it, she kissed me and said that was ok and maybe she could help....I was thinking Wow what did she just say, so I said yes if she was sure but she didn't have to....... I was wearing a sweatshirt and jeans and as I sat up Olly undid my belt and zip, my dick moved and was now poking against the front of my boxers, she said did that feel better and I laughed and said yes as it had been kind of bent before. She asked if she could see it so I pushed my boxers down and it was there pointing up at her. She was sweet and said it was the first boner she had seen in real life...I said something totally stupid like she could see it again whenever she wanted and we both laughed. She kissed me and at the same time held my dick which felt totally awesome. For the past three years or so I had wanked off most days and on occasions watching porn with two or three close friends we had wanked each other for fun but this was the first time a girl had touched my dick and it was so hot. I said that if she wanted to see it properly I would take my boxers off and she said yes. I put my jeans back on but only pulled them up to my knees and we both laughed that if anyone drove up we could be decent again in two seconds. I cuddled into her again and kissed her and caressed her boobs and she held my dick again and started playing with it, particularly watching herself moving the foreskin back and forth over my end, I told her that there was a good chance of me shooting cum out if she continued and she laughed and said not to make a mess on her. I moved a little so I was sitting more naturally on the seat rather than leaning into her, my dick was rock hard and I could feel my orgasm building, I held my boxers ready just in front of my dick and put my other hand on hers for the final couple of seconds before my cum spurted out onto them. Wow what a fantastic feeling! My first hj from a girl and we had both enjoyed it, she kissed me then watched as my dick softened and I squeezed the last drops of cum out onto my boxers. Her nipples were fully hard and as she took her blouse off to put her bra on again I gave them a gentle kiss and she said that felt good. I saw her again on the Wednesday evening, I was kicking a football around with some friends on the local playing field and she said she would come down once she had finished her schoolwork. It was about a 15 minute walk from her house on the outskirts of the village and she arrived just as it was getting dark and we were packing up. There were no showers or changing facilities just an old open fronted brick building with toilets at one end so to unwind a little we all used to sit on the edge and drink a beer before going home. Olly joined us and we all chatted for about 30 mins or so watching the sun go down. Everyone lived in different directions and a couple of the guys had bikes so when we left we were soon on our own, Olly and I were snuggling close to each other as we walked and she asked if the boxers had washed ok and I said yep I had rinsed them to get rid of the smell and stains before putting them in the laundry, this made me horny again... I went in and had a coffee with her parents who were watching a dvd then Olly came with me to the back door to say bye bye, this door is in an enclosed solid porch with total privacy so we knew we had a few minutes to ourselves. As we kissed I slid my hand under her tshirt and bra and caressed her boobs, this had become the norm I guess and as usual I was rock hard. Olly put her hand on my boner and then unzipped my shorts and got my dick out, there were no lights on but she looked down and asked if I had a handkerchief and I said yes and took some tissues from my pocket. She just kissed me and started wanking me and quite quickly she made me cum for the second time. Olly was a great friend and also a great girlfriend, I loved being with her just doing everyday stuff and any sexual fun was a bonus. The next Saturday evening my parents were away at a concert so after I got home from work Olly came round and we had the house to ourselves as we settled down to watch a dvd. We were cuddling on the sofa and pretty soon I had undone her blouse and she seemed more than happy the way things were going so I said how about going up to my room and we could cuddle properly in bed, she thought for a second or two and said okay but she was keeping her panties on and that area was out-of-bounds so I said yes that was fine....tbh I was a little disappointed but quite happy to agree to her wishes. She undressed and carefully folded her clothes then smiled at me as she got into bed, she looked absolutely amazing and I am sure I could make out a dark shadow of pubic hair through her pale blue panties, my dick was rigid again and I tried not to appear in too much of a hurry as I completely undressed and left my clothes on the floor. I had wanked off twice earlier in the day, morning shower and after work shower but was so horny....a lovely girl practically naked in my bed...wow! At first we just cuddled and it was so hot feeling skin on skin contact for the first time ever, I kissed her lips and nose and boobs and she was happy for me to push the duvet back so I could see her full body and I could see looking at me and my dick..(it's nothing special.... uncut and just under 6 inches with black pubic hair at the base but not along the shaft). We cuddled again and my dick was sort of against both our tummies, Olly held it and started wanking me again, she said she didn't really want the cum to go on her and I said that was fine and lay more on my back and when I did cum it spurted onto my stomach with Olly closely watching. Wow! Over the next few weeks we grew more confident together and she let me cum on her tummy but still kept her panties on when we were having fun so I never tried to go down there. We continued seeing each other and enjoying each others company for a couple of months, the youth club was having a weekend camp at some proper campsite about 40 miles away, I was going and so was Tony and five other girls so Olly's parents agreed that she could also go. The sleeping arrangements were two separate tented areas and everyone was told that there was a strict embargo on visiting the other tents/showers? etc. Everything went really well, there were 10 guys between three tents and the six girls in two tents, I shared with a close friend John and another guy who was ok, on the Saturday night we had a bbq and everyone went to bed fairly late and very tired, I had wanked off in the toilet block mid-afternoon and told Olly what I had done cos I had been thinking of her and she had just laughed. We had agreed that during the camp we wouldn't hang around together all the time as that would have been quite embarrassing and not what the camp was about. About 2am I woke up to see Olly undoing our tent door and sneaking in, John and the other guy were fast asleep, Olly was smiling and kissed me, I unzipped my sleeping bag and she snuggled in beside me saying everything was fine but she was awake and wondered if I was. She was wearing some loose tracksuit bottoms and a tshirt and I just had on a pair of boxers and when we cuddled I could feel that she didn't have her bra on as her boobs were so warm against my chest. We hugged each other really close, I caressed her boobs under her top and she held my dick which was sticking out of my boxers, I wondered if we would just fall asleep like this but she whispered to make sure I didn't cum on her clothes as her mother would be washing them when she got back so I said I would wriggle out of my boxers and cum on those. This only took a couple of seconds and then we cuddled again, I was mainly laying my back facing her and she was more on her side playing with my dick....she had got used to judging rhythm by now and didn't need much "guidance"....I was cupping one boob in my right hand and holding my boxers ready in my other one and loving every second of it. . Then she briefly stopped and held my right hand taking it off her boob and sliding it under the loose waistband of her bottoms, she kissed me and went back to stroking my dick again. OMG!... this was so unexpected but so much wanted.....as gently as I could I slipped inside her panties and felt her soft pubic hair......I was thinking that at any second she would pull away but she didn't, she kissed my cheek and slightly moved backwards and then I was exploring the warm wetness of her cunt..........woooooow.....two fingers inside...so good.....so unexpected OMG. I felt my climax building and quickly put my boxers by the end of my dick as the cum spurted out. Olly didn't say anything but I felt her body relax, she kissed me as I wiped my fingers on the boxers and then we cuddled and fell asleep for a couple of hours before she sneaked back to her own tent. The next morning Olly was all smiles and when someone else asked if she had slept well she laughed and said perfectly.... We never really talked about me fingering her but everything was good between us and she wanked me off down the week when we cuddled outside her back door. The Sunday after we got back I borrowed the car and we went to the coast, Olly looked lovely, she was wearing a thin cotton swirly skirt and a short sleeved loose blouse, her hair which was usually mid-brown and well below her shoulders had been lightened and cut so that it was now just below her collar..maybe three inches shorter, I asked her what her natural colour was but just laughed and said this was her summer look. She rarely used any make-up as her complexion was fine, she had blue eyes and a cheeky smile and to my eyes was perfect. On the way back we parked up in a country lane and after kissing for a few minutes Olly was undoing my shorts and I was undoing her top and bra which she had worked out how to easily take off in the back of a car and we had also realised that by moving the front seats fully forward we had much more space to stretch out in ......... I pushed my shorts and boxers down to my ankles and undid my shirt and Olly rested her head on my shoulder as she stroked rather than wanked my dick. A couple of hours earlier we had been in an amusement park and I had wanked off in the toilets as just being with Olly made me so horny and I didn't want to cum too quickly when we were together like this. I kissed and caressed her boobs and then slowly moved my hand down her tummy just to see what her reaction would be and she seemed fine, her skirt had an elasticated waistband and she moved slightly to open her legs more as I slid my hand under it and into her panties...pure heaven....just feeling her pubic hair made me so excited and I think my dick twitched in Olly's hand cos she started wanking me as two fingers slid inside her. I was a complete novice at this and just gently moved my fingers in and out, Olly kissed my cheek and a few seconds later I moved more onto my back and whispered that I was about to cum. Olly held my dick close to my own tummy and my cum spurted out onto it, she liked to see this and kept hold of my dick till it softened. I used some paper napkins to clean up then we cuddled close for a few minutes before driving home. On the Friday Olly came round to my place for tea before we both walked down to the youth club, she got on very well with my parents in the same way that hers liked me. It started to rain before club finished and Olly's brother Tony borrowed his dads car and picked us up and dropped me off first so there was no time for anything other than a quick kiss goodbye and then an urgent wank once I got inside. The next afternoon and evening my parents were out with some friends, after I got back from work Olly came round and we had some pizzas and french beers my mum had left ready then we went up to my room. She seemed in her usual good mood and helped me undo my jeans and take them and my boxers off, my dick was like semi-stiff until she touched it then Wham! rock hard. I was naked a couple of seconds later and made to take off her tshirt but she laughed and told me to get into bed, I turned the duvet half-down and lay on the bed rather than in it, holding my dick but not playing with it in case I cummed right then and there. Olly took her tshirt and bra off and as neatly placed them on my dressing table the she took her jeans off and placed them there too, she turned towards me and took her panties off and gently threw them for me to catch as she walked the couple of steps to the bed. I couldn't really see her cunt but she did have a trimmed triangle of dark brown pubic hair, she laughed and said that I had asked what her natural hair colour was and this was the easiest way to show me. Rather than lay next to me on the bed she got under the duvet and then said she was sorry and put her panties back on which were just laying by me, I kissed her and asked what was she sorry about and she said putting her panties on again but she really needed to do that. I told her that was totally good for me too and we hugged and for a split second I thought she was going to cry but she didn't. We lay on our sides on top of the bed and she snuggled up really close to me and said that it wasn't about not trusting me etc but she was so scared of getting pregnant like one of her class had that she mentally needed her panties on when cum was about. I told her that made total sense to me and that in future one of us would always have our pants on and this made her laugh. Although I hadn't touched them yet her nipples were rock hard against my chest and my dick was resting against both our tummies fairly stiff but not fully, Olly now seemed totally relaxed, she moved onto her back and looked at both our bodies and said something like Ok the deal is her panties always on and mine always off as she held my dick and started wanking me. I just lay there on my side and let it happen, she knew me and my dick well enough, as I started to cum she held it so that it spurted over her tummy rather than mine then leant forward and kissed me. WoW! We cleaned up and I pulled my boxers on and went to make us some coffee, I knew we had at least two hours before my parents were due back so we could just enjoy being together. We drank the coffee sitting up on the bed and seeing Olly's boobs from like sideways convinced me how pert and perfect they were from all angles, I told her so and she said that she wished they were bigger so I cupped one in my hand and said it fitted perfectly she smiled and cupped my soft-ish dick in her hand and said the same and we both laughed and hugged each other. She was still holding my dick and it was growing........I kissed and sucked her boobs and was now fully hard again, I put my hand on top of her panties and felt the outline of her cunt, rather than go from the top I slipped my hand inside one leg hole and gently fingered her and her response was to kiss me and build up a rhythm on my dick. This was soooooo goooood. The amount of cum wasn't as great as before and Olly let it spurt on me instead of her but I didn't care at all, she was happy and so was I. We dated for another nine months or so till I went to work away from the area, she was a lovely girl who was strong enough to say what she felt, we never progressed to oral or fucking but, guess what, it didn't matter.

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