This is a story about my best friend and me on our road to discovery. It is a recollection of our first time pleasuring each other. I really loved her and fondly remember these experiences from twenty years ago. I hope you enjoy it as much as I enjoyed putting it in writing. This is my first time ever, writing out a story, but all of you have inspired me to give it a try.
Depending on feedback, good and bad, I’d like to continue my story. Please be gentle but honest in your comments. I hope you enjoy.
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I don’t know how old we were when we first met, as it seemed we had always been friends. All I know is that Holly and I became friends sometime in Elementary School. We were just kids, innocent and pure. We lived close to each other and we would walk to and from school together. We would sometimes eat lunch at each others houses and would play together after school and on weekends. To tell the truth, I didn’t even consider her to be a girl. Holly was just a friend and we did everything together. Holly was my equal in anything physical and we had a lot of fun together. We’d ride bikes, play in the park, shoot basketball, play soccer, and just hang out lying on our backs down by the river.
I think the first time I ever realized Holly was a girl was one day in middle school. I over heard a group of boys laughing and making jokes about my best friend. As I listened, I heard them saying something, how shall I say, less than polite about Holly’s chest. I don’t remember when Holly had started developing, but on that particular day, Holly had worn a t-shirt that was a little too tight. I found out later that Holly never wore a bra as she thought they were uncomfortable. Anyways, Holly’s chest was very noticeable through the tight t-shirt. While curious, I was really embarrassed and didn’t know what to do. Fortunately, one of our teachers had noticed and talked to her mother about the situation, and from that time on, Holly always wore a bra (at least from what I could tell). Looking back, the situation was handled pretty well as Holly had been spared any future embarrassment in front of the boys. Holly was a real tomboy and had not realized that her developing physique had any effect on anybody. Like I said, we were both pretty innocent and naïve.
However, from that day on, I suddenly noticed that Holly was not one of the guys, at least not physically. Holly was becoming a young lady and as such, I had to respect that. I knew what girls were like, I had four older sisters. But Holly and I were just friends. Physically we were both developing, but the changes were just cosmetic. We weren’t any different inside. So we continued just being friends and spending time together. We did a lot of outdoor sports and played a lot of soccer with a group of other kids, but we also had our other activities and friends away from each other. I just treated her as one of the guys.
Eventually, Holly and I graduated High School together, celebrated our eighteenth birthdays, and were ready to conquer the world. I had noticed that Holly had blossomed into a beautiful young woman. Holly wasn’t the prettiest girl, but she was very attractive and had a very athletic figure. I never tried to make a pass at her as Holly was still very much a tomboy. If Holly got mad at me, she wouldn’t hesitate to slug me in the shoulder. Of course, I’d just wind up and slug her back, not hard enough to hurt her but enough to let her know I didn’t appreciate the bruise she gave me as she was very athletic and had a nice whollup. Sometimes that would lead to a serious wrestling match and half the time I’d let her get the best of me. Holly was strong, but I kept my strength in check as to not physically hurt her. We were just having fun, but I would have never forgiven myself if I had ever physically hurt her.
In those times when I let her take me, I would let Holly pin me to the ground until I cried, “Uncle!” Then Holly would usually sit on top of me as we both caught our breaths. More than once while Holly was sitting on my crotch, I’d get a huge erection. If Holly ever did notice she never said anything, but I think Holly liked to tease me as I got the distinct impression that she enjoyed grinding her crotch against mine, fully clothed that is. Holly was a tease but who was I to complain. I was enjoying it as long as she did too.
Over the previous few years I had dated other girls as I could never seem to find a way to take Holly and my friendship to the next level. In truth, I was probably scared that Holly would get mad at me and not want to have anything more to do with me. So I dated other girls I knew, while Holly and I remained good friends. Holly never seemed to care too much and we still hung out. We’d occasionally talk about the opposite sex with each other but Holly never dated and never seemed to be all that interested in boys. There were a few times when I thought that Bostancı Escort maybe Holly preferred girls, but that didn’t seem likely either. Holly just didn’t seem all that interested in sex other than the occasional crotch grinding Holly would tease me with. I was still a young, immature young adult and I didn’t know what to think. Looking back, I wish I would have just asked her.
Of the other girls I dated, I liked them all, but none of them became more than just casual friends. I mean we would sometimes hold hands and kiss, and there were even a couple of times that we got into some mutual heavy petting. After bringing one girl to orgasm that way, she was more than willing to go all the way, but for some reason, I didn’t want to go all the way. At least not with her! I don’t know. Maybe I’m a little weird that way, I wanted to do it, but on my own terms with someone I really cared about. Oh, she did jerk me off and it felt incredible, but afterwards we just held each other and kissed.
One day while in our freshmen year at the local community college, Holly came over at my house after classes. While doing some homework, out of the blue, Holly asked me if I had ever looked at a men’s magazine before. I didn’t tell her that I had a sizeable collection of my own hidden in my bedroom as she probably would have thought I was a pervert. Wait! I guess I was one, but let’s not get too personal! I asked her why she was asking. Holly said that she had been in her parent’s room one day looking for something and had come across a few magazines that her father had. Holly was curious if all men read these type of magazines and if I, specifically, read them. Read? Yeah right! ‘Looked’ would be the operative word. I was a little embarrassed and I guess Holly saw my face turn red.
I half-lied to Holly and said “Yes”, but that my older brother owned them. Right! He didn’t even live at home any longer but fortunately Holly didn’t catch that one. I asked Holly if she had looked inside any of them and she shyly replied that she had. I asked her what she thought and this time it was Holly’s turn to turn three shades of red. After patiently waiting and a little prodding, Holly said that at first she was just curious but that after a while she became interested. Holly wondered how she compared to other girls and wondered how she measured up. Oh boy! If Holly only knew! I would have loved to have shown her but I kept myself in check as thoughts that could have got me arrested in some States raced through my brain. Or, should I say my groin? I looked Holly in the eyes and told her she was the most attractive person I had ever known and that she should never doubt herself. I added that though I had never seen her without clothing, other than in a swimsuit, I thought she was more attractive than any of the women in the magazines.
Holly smiled and said, “Yeah right!”
I looked her in the eye and without thinking said, “Don’t sell yourself short! I’d pick you over any of them any day of the week!”
Holly stopped for a second as she seemed surprised, and then smiled at me. Holly leaned over and gave me big hug and said, “Thanks. I needed that. Sometimes I feel so awkward.”
Now I don’t know if it was intentional or not, but as Holly hugged me, her breasts pressed into my chest. Suddenly, Junior quickly started waking up! As we separated Holly’s hand fell from my shoulder and accidentally brushed against my growing erection. I think she noticed, as I detected a small gasp in her voice and her eyes got a little bigger. Holly just smiled at me.
I thought the conversation was over and had turned back to my books but then Holly asked me another question. “What do you think about when you look at one of those magazines? I mean, do you feel anything?”
I looked at Holly surprised and said, “I don’t know. I guess I enjoy looking at the pictures. I guess they sort of turn me on.”
“What do you mean by they turn you on,” she said.
I replied hesitantly, “Well, it’s a little embarrassing but, you know, they cause me to get an erection.”
“You mean like when I just hugged you?”
“So you noticed, eh? Yeah, like that,” I said as my face burned with embarrassment.
Holly smiled at me and leaned over and repeated the previous hug. My cock jumped a little! Holly laughed.
“Thanks,” I said. “That’s a really good way to build my confidence!”
Holly smiled at me and put her hand back on my crotch. “I’m sorry. I didn’t mean laugh. I was just…. Wow! That is really hard! Does it hurt?”
“Ahhh, not exactly,” I replied. “I guess it sort of aches, but in a really good way!”
Holly smiled and moved her hand a little. Her eyes grew in amazement as she began gently stroking my cock. “How does that feel?” she asked.
“Oh man…. That’s amazing! Please don’t stop. You’re driving me crazy!”
Holly put her entire hand around my clothed cock and rubbed me gently. I thought I was going to Ümraniye Escort pop right then and there. To my amazement, as my breathing increased, Holly’s appeared to as well. I moaned in pleasure. I leaned back in the chair and allowed Holly to do whatever she wanted to. My cock was aching and needing some serious release.
Holly looked into my eyes and smiled. Quietly she said, “I think you’re turning me on too! I feel all funny in my stomach and my vagina is aching. But, like you said, in a good way!”
“This isn’t going to ruin our friendship is it?” I asked.
“Not a chance!” Holly replied while getting up. “I’m your friend and we’re not doing anything that either of us doesn’t want.”
Holly took my hand and we walked to the sofa. We sat down next to each other and I leaned over and kissed her. She was surprised but didn’t resist. We broke apart and then Holly kissed me and climbed onto my lap, straddling my crotch, while continuing to kiss me. My cock was straining in my jeans as Holly ground her crotch against mine. We broke for air and Holly took both my hands. Smiling, Holly moved my hands to her breasts and told me squeeze them gently. As I did, I felt her nipples becoming erect. As I gently kneaded them, Holly began moaning and leaned back.
“Oh God, that feels wonderful!” she said. After a few minutes Holly added, “Would you feel embarrassed or laugh if I removed my shirt? I’ve never had any one touch me like you have today and I am so turned on. I need your hands touching my bare breast and I know I can trust you not to make fun of me.”
I paused, as I didn’t want to appear too anxious, and then said, “Only if you’d like to, but I’d really like that too.”
Slowly, Holly reached down and pulled her shirt up and over her head exposing her incredible breasts clad only in a lacy, white brassiere. I watched in amazement as Holly reached behind her back and unclasped her bra. She let it hang loose for a moment and then pulled my hands up and under her bra. I gently cupped Holly’s breasts in both hands and she let the bra fall from her shoulders. Oh god, they felt so good and it is a moment that I’ll never forget. It felt so amazing, as Holly’s nipples pressed into my hand. I moved my hands around and circled my thumb and forefinger around her nipples. I couldn’t believe how erect Holly’s nipples were and how perfect her breasts looked. I had seen a few of my girlfriend’s breasts before, but not even one of the women in the men’s magazines photos had breasts that were as perfect as Holly’s. I gently continued to massage Holly’s breasts and pinched her nipples. Holly moaned and closed her eyes. She was breathing hard and I couldn’t help myself. I leaned forward and took Holly’s right nipple into my mouth.
“Oh lord!” Holly moaned and leaned her head back. “Please don’t stop. Suck my nipples! That feels so good!”
Truth be told, it would have taken a crowbar to pry me from Holly’s incredible breasts. I sucked her nipples like I was a starving baby and she clasped her hands around my head and pulled me closer. Suddenly, Holly shuttered and moaned out loud, “Oh God! Oh God! Oh God!” and started thrashing about. Holly was moaning and grinding and massaging the back of my head as I continued sucking. After a moment, Holly pushed me back and kissed me hard. She hugged me tight and held onto to me. Then, Holly leaned into my ear and thanked me for making her feel so good.
“I don’t know what happened but it was incredible!” Holly said. “You started sucking on my breasts and sudden I felt like my body was exploding. I don’t know what happened but I know I could get used to that feeling.”
I asked Holly if she had ever felt something like that before and she replied that she hadn’t. I explained to Holly that I thought that she had had an orgasm. She just smiled and kissed me again.
“Well, then thank you for making me orgasm. It felt incredible! I’m so happy that you’d do that for me. I was so scared that you’d think I was a pervert for even suggesting doing something like this. You don’t think I’m a pervert do you?” she asked.
I smiled and kissed her. “Of course not, silly. You’re my friend. I’d be happy to make you feel that good anytime. I thought you’d think I was a pervert if I ever tried to do anything like that!”
Holly gave a small giggle and wiggled on my lap.
“Oh, I’m so sorry. I forgot about you. Is your penis still aching?” she asked.
Holly moved back a bit and looked down. My cock was bulging in my pants and she said, “Wait, stupid question!”
Looking into her face, I saw Holly watching my bulge and deciding what to do.
“Would you mind if I undid my pants and took my penis out?” I ventured.
Holly smiled and shook her head no. I undid the button at my waist and slowly lowered my zipper. Then, I had Holly raise herself up a bit so I could lift my hips and pull my pants and underwear down my thighs. Holly gasped, and sat back down.
“Touch Anadolu Yakası Escort me if you want to,” I said. “But gently, I am pretty sensitive down there right now”.
Smiling, Holly reached down, all the time watching my cock to see what would happen. I gasped and moaned.
“Oh my! You’re so warm and I can’t believe how big your penis is! Are all penises this size?” she inquired as she wrapped her hand around my cock.
“I don’t think so,” I replied. “I think they all come in different sizes, something like the different sizes of women’s breasts.”
Holly pondered that for a moment and then said, “Well in case I forget to mention it later, I think I like the size of your penis. It seems to fit my hand perfectly! Do you want me to rub your penis some more?”
I wrapped my hand around Holly’s hand and started moving her hand up and down. “Why don’t you just stroke me like that for a couple of minutes?”
Holly enthusiastically continued to stroke my cock with her hand, rubbing me up and down. I directed her to tighten her grip a bit and leaned back to enjoy her handy work (no ‘pun’ intended). My cock stretched to the maximum and pre-cum leaked from the tip. I was in heaven!
Looking at her heaving breasts and watching her stroke my cock was too much. I could feel my balls tighten and my eruption close at hand. “Careful Holly, my cock is going to explode any minute!” I warned.
I thought Holly would jump back or stop pumping but surprising she just sped up her hand movements and gripped me a little harder. God, what a feeling! It was too much and I felt the dam burst. I started shooting cum up in the air. The first spurt hit her in the face and the next couple landed on her chest. I felt like I had died, as spurt after spurt rushed out the tip of my cock. I don’t think I had ever come that much and I couldn’t believe Holly was doing it.
Slowly I came down from the high and opened my eyes. Holly was looking at me with amazement and smiling. I smiled at her and then Holly bent down and kissed me.
“Did that feel good?” she asked. “Wait, stupid question again! I guess that’s what you’d call an orgasm, eh?”
“Yes, now, THAT was an orgasm! I don’t think I’ve ever come so hard! Thank you so much,” I said as I kissed Holly back.
“What do you mean by ‘ever’?” Holly asked. “You mean you’ve done this before?”
“Not exactly,” I replied. “But we can talk about that later. We better go into the bathroom and get cleaned up, my parents will probably be back soon and I think I slimed you good.” I apologized for hitting her in the face and covering her chest with cum.
Holly smiled and said, “Don’t worry about it. It was fascinating watching you orgasm! I’ve never done anything like this and I’m glad that it was with you! Maybe we could try this again sometime?” she cautiously and coyly asked.
“Anytime you want, Holly! Anytime!”
We got off the sofa and left for the bathroom. I grabbed a washcloth and ran it under the warm water. I turned to Holly and started to wipe my cum from her face and chest. Holly’s nipples started to get erect again and I couldn’t resist leaning down and taking a nipple into my mouth. I sucked gently and she moaned. Gently Holly pushed me back and said that we’ll do that again sometime. Then, taking the wash cloth from me, she rinsed the wash cloth in the warm water and knelt down between my legs and wiped me clean. My cock immediately started growing and within a few seconds was rock hard and standing proudly at attention. Holly smiled and lightly kissed the tip of my cock.
“Did I cause that?” she asked innocently.
“Well sort of,” I mumbled. I couldn’t believe I was standing with my pants around my knees and my cock just inches from her face. Holly stroked it again and looked at it in fascination.
“Will you orgasm for me again?” Holly begged. “I want to see your penis explode again!” she said while stroking my cock slowly back and forth.
I stepped closer and asked Holly if she would take my cock into her mouth.
“I don’t know,” Holly replied. “I’ve never had a penis in my mouth before and I don’t know what to do.”
“Well, to be honest, I’ve never had one in my mouth before either…. but I’m sure we can figure it out,” I teased her.
Holly smacked me on my butt, which caused my cock to swing from side to side. She giggled in amazement while watching my cock sway. With Holly’s mouth mere inches from my cock, I grew harder and she grew more interested. All the while she slowly stroked my cock with her hands.
“God, I’m so horny! I’m sure I wouldn’t take long to have another orgasm if you put it in your mouth,” I said.
“Are you sure you want me to put it in my mouth? I might hurt you!”
I looked into Holly’s eyes and replied, “Holly, nothing would make me happier than if you’d at least try. I think there’s no way you could hurt me as long as you keep your teeth away from it.”
Hesitantly Holly replied, “Well…. I really want to make you feel good and have you orgasm again, so I guess it wouldn’t hurt to try. Your penis is so warm in my hands and I love holding it and stroking it and feeling it pulse. I can’t believe how big it can get and how purple the head gets.”