I've always wanted a friend with benefits, but I never thought it would be so easy to find one. I'm Ryan, I'm 16 years old and I live in England.
My life is fairly boring, I'm not hugely popular and I'm a virgin. My best friend is Sam who lives down my road and is three years younger than me. When we were younger we used to play football in the car park behind our houses, to the annoyance of our neighbours.
By the way Sam is not my friend with benefits, I'm definitely not gay. If you were wondering I am 5'10", brown hair, blue eyes and I have a fairly muscular build. I wouldn't say I'm the most attractive guy around but I'm not far off. Well in my opinion anyway. About 3 years ago the house next door to me was sold to one of my mother's friends. She had a daughter who was two years younger than me called Jess. She was gorgeous. She has long, straight, hazel hair that falls below her shoulders and rests on her breasts.
She had green eyes, a slightly freckled face and a well-kept figure. Sam and I didn't take long to start speaking to her; we invited her round Sam's house to get to know her. Considering she was two years younger than me she seemed quite mature, unlike Sam.
I decided in my head that if either of us was going to get this girl it would be me. This was the plan, a year later and I still hadn't done anything. I still fancied her uncontrollably but she had now been put in my 'friend zone.' I was pretty sure nothing was going to happen from that point onwards.
It was a still night in autumn and we were all watching a film at Jess' house. By the time the film was over it was fairly late so we decided to stay over for the night.
As soon as this decision was made a plan popped into my head. I knew that if my plan went well I might be able to get the chance to see Jess naked; this gave me a boner straight away.
Anyway, I continued to join in with the evenings events and let everything fall into place. I texted Jess and told her to stay awake longer than Sam, I didn't want him in the way of things. When Sam finally fell asleep at 2 O'clock in the morning, I texted Jess saying 'follow me.' I led her from the living room to the front door and quietly told her that we should sneak out.
Luckily for my plan, she agreed to it. We quietly crept out of the house and didn't speak until we were far enough away from the house. We decided to go to the school which was a two minute walk from our houses. I got to cuddle her the whole way due to the cold evening. When we got to the school I realized something that could ruin my plan, directly opposite the school was the police station.
We decided to sit in the shadow of the bordering hedge so that we were out of sight. From previous experience I knew that Jess was quite confident and easy going. I decided to see if my plan would work by suggesting that we play dares. This may sound childish but I knew that it may escalate.
We started with dares like run to one of the landmarks we could see in the school grounds, doing silly dances and shouting funny things. I got more confident as the game progressed. I suggested we went to the outdoor fitness equipment that the school had and carry on playing there. This was still in close proximity with the police station so we still had to be cautious. I decided that I had to make a move so I confidently dared her to go on one piece of apparatus in nothing but her underwear.
She agreed to this but said I had to look away. She then completed her dare with me facing the other way.
I turned round just as she was buttoning up her shirt catching a glimpse of her red laced bra. I got a boner but luckily my jeans were sturdy enough to conceal it.
I'm sure as you all know, when playing dares you take it in turns. Unfortunately Jess made me do exactly the same dare however part of the dare was that she had to watch.
I'm not sure if I imagined it but I think she was testing me as well. I removed my clothes and instantly felt the bitterness of the cold breeze. My boxers were not strong enough to hide my throbbing dick so I tried my best to keep my back to her.
I knew she had already seen my toned stomach on a previous occasion so I didn't need to show off my six-pack. Once my dare was over I decided to put my clothes back on and sat back down next to her.
I then really went for it, this was the moment where it could all go wrong. I dared her to get naked and go on each piece of apparatus then she could put her clothes back on. There was a pause; I thought I had ruined the friendship I had taken a year to build. To my surprise she unbuttoned her top. Her navel was beautiful; her breasts, thought still hidden by her bra, looked amazing. Once her top was off she changed the dare.
She said she'd only do it if I did it at the same time as her and went ahead so that I couldn't see her. Although this meant I'd only catch glimpses I still agreed. We stood back to back and got fully undressed, then I shouted go and ran to the first apparatus. Running with a semi is not very easy. I could just hear giggling coming from behind me. As I ran between the apparatus I turned my head to see her. It was so dark that I could only just see her. It was very unclear but she was beautiful.
She had one hand over her boobs and the other over her pussy so I couldn't actually see her properly. Once we got to the final piece I told her to keep her clothes off. We went and sat by a big tree so we couldn't be seen from the road or the police station. We sat there, I had my arm around her shoulder, my dick was now rock hard and in full view so she could see it. She still chose to keep her privates covered though.
We just sat there and talked for a while before she became relaxed. I'm not sure if it was intentional but the hand covering her boobs fell and lay with the other over her pussy. Her tits were amazing, her nipples were hard and pointy because of the cold night. Because my arm was around her neck my hand was within centimetres of her boob. I had to resist grabbing it. I'd never seen a real girl naked before, let alone touch a boob.
As we sat there and became more and more comfortable, I decided to move things on again. I came up with another dare. "I dare you to touch my dick." She giggled nervously and then with her index finger she gently poked about half way down my shaft.
She was surprised at how warm it was so I cheekily said you can gold it if you want. I said it in a sarcastic tone, so either her hands were really cold or she was horny as she did indeed hold it. Her hands were much smaller than mine and looked tiny wrapped around my throbbing penis.
After a little while of just holding it she started playing with it. Almost as if she was a toddler playing with a new toy.
I decided that this was the chance for me to get my first contact with a tit. I reached out with my hand and gently squeezed it. It felt so good, so soft, so amazing. She didn't seem to mind me touching her so I raised my other hand and felt both boobs at the same time. I pressed the two together and massaged them gently, this was my first time and I didn't want to do anything wrong. I tweaked her nipples gently and then clasped her boobs gently and bounced them up and down.
My dick was so stiff by now. I dared her to start jerking me off. At first she seemed a bit reluctant but then slowly started pumping on my shaft. I couldn't believe that she was actually going along with it. I didn't want this moment to end, so when she stood up and went over to where her clothes were I quickly followed and grabbed her around the waist and put my lips to hers and kissed her.
As we embraced I felt her warm boobs pressed against my chest and I could feel my dick digging into her legs. We were still kissing when I thought I'd take it to the next level. I lowered my hand and gently rubbed her pussy.
It was dripping wet and really warm. I gently pressed my fingers against it, I didn't really know what to do because of my lack of experience.
I felt around for a bit just to get used to the feeling. I felt what I think was her clit, I rubbed it gently and she let out a quiet moan. Gaining confidence I felt around a bit more. Without meaning to my fingers slipped deep into her pussy. My fingers were engulfed. She was so tight, it felt amazing. I could only just fit my index and middle finger in. I think I hurt her a bit, but she insisted that I continue. I slowly pushed my fingers in and out.
She kept moaning softly as I continued to kiss her. I felt bad that I was using one of my best friends, but it felt amazing and I wasn't going to complain. She started pumping on my dick again, I thought I was actually going to explode, cum started shooting out and went all down her front.
She was butt naked, dripping with my cum. This was understandably the best moment of my life, however we soon realised that she would have to put her clothes back on.
She scooped up as much of my cum as she could and wiped it on a leaf off the floor. She then slipped her clothes back on, I followed her actions and also got dressed. It was a slow walk back to the house, we didn't say much, just enjoyed each other's presence. When we got back we quietly opened the door. I went straight back to the sofa a lay under the covers and let her go and clean up in the bathroom.
I don't know how long she took because I fell asleep before she returned. I dreamed about what had happened. In the morning we didn't say anything about it to each other. However she did give me a very cheeky smile from across the room. In return I mouthed "thank you" in her direction. To this day Jess has been my friend with benefits and to this day not a soul has been told. Well that is, until now. This is how I got my friend with benefits.
Absolutely 100% of this story is true apart from our names. I may write more stories about other things we have done since. Please rate this story and leave your comments below.
Thank you, PornPiggy.