MY FIRST LESBIAN EXPERIENCE
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For the past 8 years, I've been harboring a guilty little secret, which I've never spoken to anyone about. Not to my lovers, not to my best friends, not to anyone. It's one of those secrets that's too embarrassing to tell, but too erotic to keep bottled up inside. It's something I've played over and over in my mind at least a hundred times since it happened, each time bringing back at least a little bit of the feeling I experienced that night.
Recently, I've begun to discover the enjoyment of reading erotic stories, and after several weeks of thinking about this, I've decided that the only way to get this secret off my chest is to share it with someone... anyone... by writing down what happened that night.
Unlike most of the stories on this site, what I'm about to describe is not a fantasy. This is what really happened. As I mentioned, this is something I have thought about for years, so, although some of the details may escape me, I remember this night more vividly than any other night of my entire life.
This story involves my friend Kelly (not her real name) and I. Best friend, to be more specific. We met at the beginning of our freshman year in High School, and we soon became inseparable. Kelly and I did practically everything together. We were both smart k**s, in all of the accelerated & honors classes, and each year, we would plan our schedules together so that we could take the same classes. We had the same lunch periods, gym classes, and we were both in orchestra together... she played flute, and I played clarinet. We studied together, worked on group projects together, and even got in trouble together. We had the occasional fight, but it never usually lasted more than a day or two.
I couldn't even begin to tell you what I liked about her. It was pretty much... everything. She was smart, funny, she had a great personality. Like myself, she was an over-achiever, both in class and in regards to extra-curricular activities. We liked the same movies and music, the same TV shows; you name it.
I guess the best way to describe Kelly is that she was a bit of a Tomboy. She was always wearing jeans and sweatshirts. Thinking back, I have a hard time picturing her in anything else. It's not that she wasn't attractive; she just never dressed the part. There were a few occasions... the Junior Prom, the Senior Ball, our Orchestra Concerts... where she had her hair done, her nails manicured, a dress or skirt on, and she looked amazing! But most of the time, it was "dress down" day for her. As much as I tried to coax her into getting "prettied up" more often, that's just who she was.
It's too bad. She was about 5'5" (slightly shorter than me), with pale blue eyes and shoulder length hair. She's naturally a light brunette, but she would frequently color her hair so that it was more of a reddish color. Not, like, fire engine red or anything, but a natural, vibrant, healthy looking red. I remember her hair as always being very soft and thick. I always thought she had nicer hair than mine, but she never really did anything with it. To describe her figure, I would use the word 'voluptuous'. She certainly wasn't fat, but she had a few extra pounds around the tummy. Her chest was a 36C, making her a bit more top heavy compared to the proportions of her hips and legs. She hated sports, but her legs and arms always seemed to be well toned. Kelly had amazing skin, or at least by my standards. She was half Irish, so her complexion was very fair. There were a few freckles on her face, but they were light, and you could only see them when you were up close. What I remember the most about her skin was that it was soft and smooth. Maybe over the years, this aspect has been exaggerated in my mind, but I can't recall anyone else I know whose skin was that soft and smooth.
I was also quite thick in my teens (and even now, for that matter). My breasts were always a bit larger than hers, but I had quite a bit more padding in my rear end too. Not to the point of "bubble butt", but definitely a voluptuous derriere. I've had long brown hair as long as I can remember. In contrast to Kelly, though, I was definitely more of a girly-girl. I liked having my hair done & painting my nails, and my clothes were trendier & sexier. Not that I dressed trampy or anything, but I would occasionally wear skirts and short shorts to show off my legs.
When it came to dating, though, Kelly and I were complete opposites. I, on the one hand, had dated about 5 or 6 guys throughout High School. I lost my virginity at the end of my sophomore year, and ended up having sex with 2 different guys over the next 2 years. They were all steady boyfriends; I wasn't into one-night stands.
Kelly, on the other hand, was not much into dating at all. Throughout her 4 years, there was only one guy she dated on and off for a few months. It wasn't that she didn't have the opportunity. As I said, despite the fact that she never dressed up, she was cute and had a great personality, so there were certainly a few guys that tried to go out with her. She just wasn't interested. And it wasn't that they were unattractive or nerdy. Even when we discussed the "hot" guys at school, she never seemed interested in them. At this point, you're probably thinking that she's a lesbian, but that's not the case either. I know for a fact that she wasn't interested in girls. After a while, I just began to think of her as asexual in a way. She just didn't seem interested in dating or boys or sex or any of that.
Although I got my driver's license when I was 16, I didn't have a car because my family couldn't really afford another one. At some point, Kelly's grandfather had bought a new car, so he gave her his old one. She would always drive down and pick me up, and we'd usually hang out at her house. It was a 2-story house, with 3 bedrooms upstairs. Her father died when she was very young, and although she had an older brother and sister, both of them were in college, so she lived alone with her mom. Kelly's bedroom was upstairs. She actually had the whole floor to herself. Her mom had polio when she was young (I guess that was before Polio shots came out), and as a result, one of her legs wasn't so good, so her bedroom was downstairs. She hardly ever came upstairs, maybe 2 or 3 times a year, so we never really got bothered when we were up there.
Kelly also had an above ground pool in her backyard, which is another reason I liked hanging out over there. It was great during the hot summers. As I said before, Kelly wasn't really into boys, so it was usually just her and me in the pool, and sometimes her neighbor. I think he was a year ahead of us in school.
At some point during my senior year, I began to feel some sort of attraction to Kelly. I couldn't even tell you what triggered it, but over the span of a month or two, it definitely got stronger. I think it may have just started out as some sort of crush, and just developed from there. Kelly & I were both born in January; I was 2 weeks older than her. From what I can recall, it was shortly after we both turned 18 that I began to have these feelings.
As you may have gathered from my description of her, Kelly was quite modest with her body. Of course I had seen her in her swimsuit, and even her underwear...we used to change for gym class together, but I had never seen her in anything less than a bra and panties. It's something I had never given much thought to, but at some point, I began to wonder what she looked like underneath... without a bra, without her panties, without a swimsuit... naked. I think it began more out of curiosity than anything, but then I began to wonder more and more, and it eventually developed into something sexual. I began to enjoy looking at her when she changed, always trying to get a peek at her rear end as she bent over to pick her gym shorts off the floor. I was very discreet about it. After all, I know that Kelly wasn't interested in girls, and I certainly didn't want to ruin our friendship over something this frivolous. Still, I couldn't help but wonder what her breasts really looked like. Were the areolas big? Were they light pink as I suspected? Was she trimmed down there? Was it thick? Dark Brown? Light Brown? As the weeks went on, I began to ponder more about it, and even fantasize about her.
It was in early or middle March, a Saturday night that I was at her house. I think we had rented a movie and were watching it up in her room. It was the sort of night that we'd had a hundred times before. After the movie ended, we hung out a little bit, and when it got late, Kelly and I got our coats on so that she could drive me home. As we went downstairs, we could see through the front window that there was a huge snowstorm outside. We lived in upstate New York, so although this wasn't a big surprise, I don't think either of us was expecting that we'd get dumped on this much. We both figured that it was stupid to drive me home on such slippery roads, so I called my mom up and told her I was going to spend the night at Kelly's, just as I had done dozens of times before.
I'm pretty sure we went back upstairs and watched a little more TV before we decided to go to sleep. Kelly let me borrow a pair of her pajama bottoms and a t-shirt. She went to the bathroom and got changed into a pair of her own pajamas. I will never forget that they were blue and green flannel PJs. It's just one of those things that I think of every time I re-play that night in my mind. Not sure exactly what I changed into... just that it was pajama bottoms and a t-shirt.
When she came out of the bathroom, I went in and got ready. Since I wasn't prepared to spend the night, I didn't have my toothbrush with me, so I'm pretty sure I just used some of her mouthwash to rinse out. She must have gone downstairs when I was in there, because when I came back to her room, I didn't see her. I hopped in bed and waited for her to come back up and shut the light off. Kelly and I had been having sleepovers for years now, and I always slept in the bed with her. It was a Queen size, so there was room for both of us. As I lay under the covers, I realized that this was the first sleepover we were having since I had become "attracted" to her. Although all kinds of fantasies about Kelly began to run through my mind, I'm a very realistic and rational thinking person, and I knew that it would never be anything more than that.
After a minute or 2, Kelly came back upstairs. She turned off the light and got into bed right next to me. For the first time in my life, I was completely intoxicated with the smell of her hair. I was practically overcome by the fantastic feminine scent of it, resting gently on her pillow not more then a couple of inches from my face.
We talked for a few minutes about something, I think. Then we turned away from each other and went to sleep. Well, she did anyway. I laid there with my eyes closed for probably a good half an hour or so. I just couldn't keep my mind off of her. And lying there right next to her, it was practically torture not being able to touch her. I tried to think about other things... school, the movie we just watched, what college would be like, anything to take my mind off the subject. Eventually, I was able to fall asleep.
And I stayed asleep, for maybe 2 or 3 hours. I think I woke up at about 3 a.m. to go to the bathroom, and when I came back to bed, I laid there for another 15 or 20 minutes, imagining what it would be like to touch her... to feel her breasts, to kiss her, to see her naked. I tried to fall asleep, I really tried. At this point, I began to seriously consider a plan. I knew Kelly was a heavy sleeper. Heavy isn't even the word. She slept like the dead. It's almost impossible to wake her up in the morning. I figured it wouldn't hurt if I just put my arm over her. I could hear her snoring a little, and I figured if she woke up, I could just pretend I was sleeping, and she wouldn't think anything of it, other than that I had rolled over during the night.
After a few more minutes of lying there stiff as a board, I decided to go for it. I rolled over gently, so that I was facing her back. Both of my arms were under the covers. She was still snoring, so I went ahead and put an arm around her, still under the covers. I was pressed against her back, with my arm over her, my hand resting lightly against her stomach. I froze in this position for several minutes. I was almost too afraid to move a muscle, but I began to tell myself "Whatever happens, just pretend you're asleep and everything will be fine." I managed to nudge my hand up an inch, and then a few more, till the side of my finger was touching the bottom of her breast.
It was like a spark of electricity at that moment, I could barely contain my excitement. Everything was going fine so far, so I continued to move my arm up a bit more until I was cupping her breast in my hand. I think I held this position as still as a statue for a minute or two before I began to massage it. It was truly a wonderful and erotic experience. Although my breasts were even bigger than Kelly's, and I had felt them hundreds of times, feeling her chest for the first time was indescribable. As the minutes went by and she continued to snore, I got bolder and started to brush her nipple through the pajama top with my thumb, pinching it lightly, and then a bit more.
It was at about this moment that I got the scare of my life! She made some kind of loud snore/clearing her throat sound, and then rolled towards me a little so that she was on her back. I thought she had woken up, and I froze in my position, pretending to be sound asleep. It turned out to be nothing, so after catching my breath for a moment, I continued to massage her breast before moving to the other one.
I gave it the same treatment: the massaging, the rubbing, pinching her nipple lightly, squeezing it gently in my hand. I began to feel more confident that she was sound asleep and would never suspect anything. As I felt her nipples hardening through the pajama top, I knew that at least on some subconscious level, she was enjoying this. I suppose it had been about 20 minutes since I first began to touch her, and I decided to go a step further.
I slid my hand down her torso, inch by inch... slowly. I reached her tummy, paused, and then continued down. I remember reaching her waistband and thinking that this was some kind of "border" that I shouldn't cross, but my emotions got the better of me and I continued down over the front of her pajama bottoms.
Finally, my fingers had reached their destination! Words cannot even begin to describe the way I felt at that moment! My heart was pounding in my chest, I was breathing heavy, and my mouth was dry. I think it was the most aroused and excited and naughty I've ever felt in my entire life. My best friend Kelly was sleeping next to me, and I had my hand practically right on her pussy.
To be honest with you, I don't know what I was doing with myself at this point. I know I was wet and completely aroused. I think I may have been touching myself a little, but I didn't want to cause any more motion than I had to. After all, I could touch my pussy any night I wanted to, but tonight, I was only interested in hers.
Her legs were together, I remember that. I was only able to get one finger between them to rub her there. I slid it back and forth for at least a minute or two before I noticed that her breathing began to change. Instead of the light snoring sounds she had been making, she started to breath heavier... the kind of breathing you do when you're aroused. Her head moved from side to side a little, and I knew that she must have been enjoying this. Maybe she was dreaming that some guy was feeling her... I don't know. But whatever it was, she was becoming visibly aroused by it.
To my surprise, her legs spread apart just a little more. I couldn't believe it! I took the opportunity to slide the rest of my fingers between her legs and rub against her pajama-covered clit. It was at this point that I realized that the crotch of her pajamas was warm and wet with her juices. This got me even more aroused! I couldn't help but press harder and rub more firmly against her, trying to focus on where I thought her clit was. As I did this, her breathing got even heavier, and her body moved even more, rocking, bucking against my hand. Even though I got more and more aroused, I also got more and more scared that she would wake up. I decided to quit while I was ahead, and pulled my hand back away from her. I laid there for a few minutes, almost in disbelief at what had just happened. And not a moment too soon.
Within about 5 minutes, her dog started barking. He did this every once in awhile. Someone was probably turning around in her driveway. Whatever the reason, it woke her up. I was SOOOOO glad I stopped when I did. I would have been mortified if she caught me with my hand down there. Even if I was pretending to be asleep, it's still an embarrassing situation. I felt her get up and go in the hall, and she told the dog to shut up. She went to the bathroom, because I heard the toilet flush. While she was in there, I took the opportunity to smell my fingers. Wow! What an incredible scent! I will never forget that smell as long as I live. Besides my own, it was the first pussy I ever smelled. I licked my fingers, but honestly, all I could taste was my own sweat. I was so nervous!
When she came back, I had my eyes closed, pretending to be asleep. She lay down next to me, and I was making my own little "snoring" sounds, so that she'd think I was sleeping the whole time and wouldn't get suspicious.
After a few minutes, I could feel her sort of nuzzling her back against me. She must have thought I was asleep, because she took my arm and placed it over her. Once again, my hand was on her tummy, but as she did this, my finger had brushed against the side of her leg, and it was then that I knew she had taken her pajama bottoms off in the bathroom. I couldn't believe it! She must have been just as aroused as I was!
With my arm over her, she backed herself up against me, snuggling up. I didn't know what to do. I just kept pretending I was asleep. I kept up my snoring act, but I think she was still awake. With my hand on her stomach, I could feel her moving under the sheets. I realized that she was secretly unbuttoning her pajama top. I knew for sure when I felt the fabric get gently tugged from under my hand, and my fingers found themselves touching the bare skin on her stomach.
Over the course of the next few minutes, I kept my hand limp, and she squirmed her body around, gradually nudging my hand up over her breast. There were probably a billion thoughts running through my head at that very moment, but I stuck to my act and pretended to sleep. Before I knew it, her hand was on top of mine, and she began to lightly squeeze it, so that my hand would squeeze her breast. She did this a few times, and then eventually eased up. Following her lead, I continued to squeeze it, all the while making my snoring sounds. She never suspected I was awake.
As my hands blindly groped her chest, my fingers fumbled around her nipples. I didn't want her to think I was too aware of what was going on. I could hear light sighs coming from her lips, and it sent shivers through my entire body like nothing else ever has.
With my eyes closed, and the covers over both of us, it was hard to tell exactly what was going on, but when I heard the sound of fabric being rubbed, I immediately knew what Kelly was doing. She had worked her hand down between her legs as was masturbating through her panties. This went on for several minutes, and I almost came from the thought of it!
Just like before, she began to nudge my hand, but this time, downwards. She subtly guided it down her body, so as not to "wake me up". I knew exactly what she was doing, so I played along. With my limp hand on the front of her panties, she guided my fingers down between her legs. When I felt how completely SOAKED her panties had gotten, I almost gasped out loud! They were just... soooooo wet!
Now, as a point of reference, since that time, I've had sex with about 8 or 9 other girls. All girls are different... some girls get very wet, some don't. There have been occasions where I've gotten very wet myself. I even had one very experienced boyfriend tell me that I was the wettest girl he was ever with. But believe me when I tell you, Kelly was in an ENTIRELY different league of wetness. Her panties where just so slippery, and absolutely drenched... from the crotch halfway up the front!
Just like with her breast, she pressed my fingers against her panties a few times, until I began to do it on my own. When she moved her hand away, I pretended to fumble around down there. I wanted to appear as "asleep" as I could. My fingers glided across the surface of the panties as I pressed firmly against her clit. I could actually feel it through the fabric now, and as I massaged it, Kelly bucked her hips to put more pressure on the area. As much as I wanted to slide my fingers in her panties, I didn't want to be too obvious.
My patience paid off. She nudged my hand up to her stomach, and I thought that was the end of it, but I felt her lift her body up and slide her panties down. I think she only slid them a few inches down her thighs, but that was enough. Kelly nudged my hand back down, and my fingers worked their way through the soaked bush between her legs. It was then that I realized she didn't trim herself, but I didn't care. It felt wonderful! I rubbed her bare clit like the world was about to end. As she bucked her hips, I moved my hand down deeper between her legs.
Before I could stop myself, I plunged a finger inside of her. Within about 2 seconds, I could sense her body tense up. I think this was the moment she had her orgasm. She held her breath for about 15 seconds, while my finger went in and out of her. As her muscles relaxed, she immediately moved my hand away from her. I guess she was too sensitive.
As I lay there, still pretending to sleep, I could tell she was pulling her panties back up and buttoning her pajama top. After a few more minutes, she got up and went to the bathroom again. Since I was so close to orgasm, I quickly made myself cum while I licked Kelly's syrup off my fingers. I would rank that in the top 3 orgasms I've ever had in my life. By the time she came back, her pajama bottoms where on, and I was rolled over, "asleep".
When we woke up the next morning, neither of us said a word about it. And that was it. It never happened again. To this day, I'm convinced that she thought I was sleeping the whole time.
After we graduated, we went to different colleges. We saw each other during summer and breaks, but after college, she moved to the Midwest and we kind of lost touch.
Regardless, nothing can shake the memory I have of that night. I don't know why I didn't pursue her more after that. Maybe because I don't think either of us was ready for that kind of relationship. Who knows. All I know is that I feel better after getting this off my chest.
If there is anyone out there that has been through a similar experience, I would love to hear from you, so I don't feel like I'm the only one that's ever tried something like this. I think Kelly and I both enjoyed what happened that night, so I guess that's all that matters.
Recently, I've begun to discover the enjoyment of reading erotic stories, and after several weeks of thinking about this, I've decided that the only way to get this secret off my chest is to share it with someone... anyone... by writing down what happened that night.
Unlike most of the stories on this site, what I'm about to describe is not a fantasy. This is what really happened. As I mentioned, this is something I have thought about for years, so, although some of the details may escape me, I remember this night more vividly than any other night of my entire life.
This story involves my friend Kelly (not her real name) and I. Best friend, to be more specific. We met at the beginning of our freshman year in High School, and we soon became inseparable. Kelly and I did practically everything together. We were both smart k**s, in all of the accelerated & honors classes, and each year, we would plan our schedules together so that we could take the same classes. We had the same lunch periods, gym classes, and we were both in orchestra together... she played flute, and I played clarinet. We studied together, worked on group projects together, and even got in trouble together. We had the occasional fight, but it never usually lasted more than a day or two.
I couldn't even begin to tell you what I liked about her. It was pretty much... everything. She was smart, funny, she had a great personality. Like myself, she was an over-achiever, both in class and in regards to extra-curricular activities. We liked the same movies and music, the same TV shows; you name it.
I guess the best way to describe Kelly is that she was a bit of a Tomboy. She was always wearing jeans and sweatshirts. Thinking back, I have a hard time picturing her in anything else. It's not that she wasn't attractive; she just never dressed the part. There were a few occasions... the Junior Prom, the Senior Ball, our Orchestra Concerts... where she had her hair done, her nails manicured, a dress or skirt on, and she looked amazing! But most of the time, it was "dress down" day for her. As much as I tried to coax her into getting "prettied up" more often, that's just who she was.
It's too bad. She was about 5'5" (slightly shorter than me), with pale blue eyes and shoulder length hair. She's naturally a light brunette, but she would frequently color her hair so that it was more of a reddish color. Not, like, fire engine red or anything, but a natural, vibrant, healthy looking red. I remember her hair as always being very soft and thick. I always thought she had nicer hair than mine, but she never really did anything with it. To describe her figure, I would use the word 'voluptuous'. She certainly wasn't fat, but she had a few extra pounds around the tummy. Her chest was a 36C, making her a bit more top heavy compared to the proportions of her hips and legs. She hated sports, but her legs and arms always seemed to be well toned. Kelly had amazing skin, or at least by my standards. She was half Irish, so her complexion was very fair. There were a few freckles on her face, but they were light, and you could only see them when you were up close. What I remember the most about her skin was that it was soft and smooth. Maybe over the years, this aspect has been exaggerated in my mind, but I can't recall anyone else I know whose skin was that soft and smooth.
I was also quite thick in my teens (and even now, for that matter). My breasts were always a bit larger than hers, but I had quite a bit more padding in my rear end too. Not to the point of "bubble butt", but definitely a voluptuous derriere. I've had long brown hair as long as I can remember. In contrast to Kelly, though, I was definitely more of a girly-girl. I liked having my hair done & painting my nails, and my clothes were trendier & sexier. Not that I dressed trampy or anything, but I would occasionally wear skirts and short shorts to show off my legs.
When it came to dating, though, Kelly and I were complete opposites. I, on the one hand, had dated about 5 or 6 guys throughout High School. I lost my virginity at the end of my sophomore year, and ended up having sex with 2 different guys over the next 2 years. They were all steady boyfriends; I wasn't into one-night stands.
Kelly, on the other hand, was not much into dating at all. Throughout her 4 years, there was only one guy she dated on and off for a few months. It wasn't that she didn't have the opportunity. As I said, despite the fact that she never dressed up, she was cute and had a great personality, so there were certainly a few guys that tried to go out with her. She just wasn't interested. And it wasn't that they were unattractive or nerdy. Even when we discussed the "hot" guys at school, she never seemed interested in them. At this point, you're probably thinking that she's a lesbian, but that's not the case either. I know for a fact that she wasn't interested in girls. After a while, I just began to think of her as asexual in a way. She just didn't seem interested in dating or boys or sex or any of that.
Although I got my driver's license when I was 16, I didn't have a car because my family couldn't really afford another one. At some point, Kelly's grandfather had bought a new car, so he gave her his old one. She would always drive down and pick me up, and we'd usually hang out at her house. It was a 2-story house, with 3 bedrooms upstairs. Her father died when she was very young, and although she had an older brother and sister, both of them were in college, so she lived alone with her mom. Kelly's bedroom was upstairs. She actually had the whole floor to herself. Her mom had polio when she was young (I guess that was before Polio shots came out), and as a result, one of her legs wasn't so good, so her bedroom was downstairs. She hardly ever came upstairs, maybe 2 or 3 times a year, so we never really got bothered when we were up there.
Kelly also had an above ground pool in her backyard, which is another reason I liked hanging out over there. It was great during the hot summers. As I said before, Kelly wasn't really into boys, so it was usually just her and me in the pool, and sometimes her neighbor. I think he was a year ahead of us in school.
At some point during my senior year, I began to feel some sort of attraction to Kelly. I couldn't even tell you what triggered it, but over the span of a month or two, it definitely got stronger. I think it may have just started out as some sort of crush, and just developed from there. Kelly & I were both born in January; I was 2 weeks older than her. From what I can recall, it was shortly after we both turned 18 that I began to have these feelings.
As you may have gathered from my description of her, Kelly was quite modest with her body. Of course I had seen her in her swimsuit, and even her underwear...we used to change for gym class together, but I had never seen her in anything less than a bra and panties. It's something I had never given much thought to, but at some point, I began to wonder what she looked like underneath... without a bra, without her panties, without a swimsuit... naked. I think it began more out of curiosity than anything, but then I began to wonder more and more, and it eventually developed into something sexual. I began to enjoy looking at her when she changed, always trying to get a peek at her rear end as she bent over to pick her gym shorts off the floor. I was very discreet about it. After all, I know that Kelly wasn't interested in girls, and I certainly didn't want to ruin our friendship over something this frivolous. Still, I couldn't help but wonder what her breasts really looked like. Were the areolas big? Were they light pink as I suspected? Was she trimmed down there? Was it thick? Dark Brown? Light Brown? As the weeks went on, I began to ponder more about it, and even fantasize about her.
It was in early or middle March, a Saturday night that I was at her house. I think we had rented a movie and were watching it up in her room. It was the sort of night that we'd had a hundred times before. After the movie ended, we hung out a little bit, and when it got late, Kelly and I got our coats on so that she could drive me home. As we went downstairs, we could see through the front window that there was a huge snowstorm outside. We lived in upstate New York, so although this wasn't a big surprise, I don't think either of us was expecting that we'd get dumped on this much. We both figured that it was stupid to drive me home on such slippery roads, so I called my mom up and told her I was going to spend the night at Kelly's, just as I had done dozens of times before.
I'm pretty sure we went back upstairs and watched a little more TV before we decided to go to sleep. Kelly let me borrow a pair of her pajama bottoms and a t-shirt. She went to the bathroom and got changed into a pair of her own pajamas. I will never forget that they were blue and green flannel PJs. It's just one of those things that I think of every time I re-play that night in my mind. Not sure exactly what I changed into... just that it was pajama bottoms and a t-shirt.
When she came out of the bathroom, I went in and got ready. Since I wasn't prepared to spend the night, I didn't have my toothbrush with me, so I'm pretty sure I just used some of her mouthwash to rinse out. She must have gone downstairs when I was in there, because when I came back to her room, I didn't see her. I hopped in bed and waited for her to come back up and shut the light off. Kelly and I had been having sleepovers for years now, and I always slept in the bed with her. It was a Queen size, so there was room for both of us. As I lay under the covers, I realized that this was the first sleepover we were having since I had become "attracted" to her. Although all kinds of fantasies about Kelly began to run through my mind, I'm a very realistic and rational thinking person, and I knew that it would never be anything more than that.
After a minute or 2, Kelly came back upstairs. She turned off the light and got into bed right next to me. For the first time in my life, I was completely intoxicated with the smell of her hair. I was practically overcome by the fantastic feminine scent of it, resting gently on her pillow not more then a couple of inches from my face.
We talked for a few minutes about something, I think. Then we turned away from each other and went to sleep. Well, she did anyway. I laid there with my eyes closed for probably a good half an hour or so. I just couldn't keep my mind off of her. And lying there right next to her, it was practically torture not being able to touch her. I tried to think about other things... school, the movie we just watched, what college would be like, anything to take my mind off the subject. Eventually, I was able to fall asleep.
And I stayed asleep, for maybe 2 or 3 hours. I think I woke up at about 3 a.m. to go to the bathroom, and when I came back to bed, I laid there for another 15 or 20 minutes, imagining what it would be like to touch her... to feel her breasts, to kiss her, to see her naked. I tried to fall asleep, I really tried. At this point, I began to seriously consider a plan. I knew Kelly was a heavy sleeper. Heavy isn't even the word. She slept like the dead. It's almost impossible to wake her up in the morning. I figured it wouldn't hurt if I just put my arm over her. I could hear her snoring a little, and I figured if she woke up, I could just pretend I was sleeping, and she wouldn't think anything of it, other than that I had rolled over during the night.
After a few more minutes of lying there stiff as a board, I decided to go for it. I rolled over gently, so that I was facing her back. Both of my arms were under the covers. She was still snoring, so I went ahead and put an arm around her, still under the covers. I was pressed against her back, with my arm over her, my hand resting lightly against her stomach. I froze in this position for several minutes. I was almost too afraid to move a muscle, but I began to tell myself "Whatever happens, just pretend you're asleep and everything will be fine." I managed to nudge my hand up an inch, and then a few more, till the side of my finger was touching the bottom of her breast.
It was like a spark of electricity at that moment, I could barely contain my excitement. Everything was going fine so far, so I continued to move my arm up a bit more until I was cupping her breast in my hand. I think I held this position as still as a statue for a minute or two before I began to massage it. It was truly a wonderful and erotic experience. Although my breasts were even bigger than Kelly's, and I had felt them hundreds of times, feeling her chest for the first time was indescribable. As the minutes went by and she continued to snore, I got bolder and started to brush her nipple through the pajama top with my thumb, pinching it lightly, and then a bit more.
It was at about this moment that I got the scare of my life! She made some kind of loud snore/clearing her throat sound, and then rolled towards me a little so that she was on her back. I thought she had woken up, and I froze in my position, pretending to be sound asleep. It turned out to be nothing, so after catching my breath for a moment, I continued to massage her breast before moving to the other one.
I gave it the same treatment: the massaging, the rubbing, pinching her nipple lightly, squeezing it gently in my hand. I began to feel more confident that she was sound asleep and would never suspect anything. As I felt her nipples hardening through the pajama top, I knew that at least on some subconscious level, she was enjoying this. I suppose it had been about 20 minutes since I first began to touch her, and I decided to go a step further.
I slid my hand down her torso, inch by inch... slowly. I reached her tummy, paused, and then continued down. I remember reaching her waistband and thinking that this was some kind of "border" that I shouldn't cross, but my emotions got the better of me and I continued down over the front of her pajama bottoms.
Finally, my fingers had reached their destination! Words cannot even begin to describe the way I felt at that moment! My heart was pounding in my chest, I was breathing heavy, and my mouth was dry. I think it was the most aroused and excited and naughty I've ever felt in my entire life. My best friend Kelly was sleeping next to me, and I had my hand practically right on her pussy.
To be honest with you, I don't know what I was doing with myself at this point. I know I was wet and completely aroused. I think I may have been touching myself a little, but I didn't want to cause any more motion than I had to. After all, I could touch my pussy any night I wanted to, but tonight, I was only interested in hers.
Her legs were together, I remember that. I was only able to get one finger between them to rub her there. I slid it back and forth for at least a minute or two before I noticed that her breathing began to change. Instead of the light snoring sounds she had been making, she started to breath heavier... the kind of breathing you do when you're aroused. Her head moved from side to side a little, and I knew that she must have been enjoying this. Maybe she was dreaming that some guy was feeling her... I don't know. But whatever it was, she was becoming visibly aroused by it.
To my surprise, her legs spread apart just a little more. I couldn't believe it! I took the opportunity to slide the rest of my fingers between her legs and rub against her pajama-covered clit. It was at this point that I realized that the crotch of her pajamas was warm and wet with her juices. This got me even more aroused! I couldn't help but press harder and rub more firmly against her, trying to focus on where I thought her clit was. As I did this, her breathing got even heavier, and her body moved even more, rocking, bucking against my hand. Even though I got more and more aroused, I also got more and more scared that she would wake up. I decided to quit while I was ahead, and pulled my hand back away from her. I laid there for a few minutes, almost in disbelief at what had just happened. And not a moment too soon.
Within about 5 minutes, her dog started barking. He did this every once in awhile. Someone was probably turning around in her driveway. Whatever the reason, it woke her up. I was SOOOOO glad I stopped when I did. I would have been mortified if she caught me with my hand down there. Even if I was pretending to be asleep, it's still an embarrassing situation. I felt her get up and go in the hall, and she told the dog to shut up. She went to the bathroom, because I heard the toilet flush. While she was in there, I took the opportunity to smell my fingers. Wow! What an incredible scent! I will never forget that smell as long as I live. Besides my own, it was the first pussy I ever smelled. I licked my fingers, but honestly, all I could taste was my own sweat. I was so nervous!
When she came back, I had my eyes closed, pretending to be asleep. She lay down next to me, and I was making my own little "snoring" sounds, so that she'd think I was sleeping the whole time and wouldn't get suspicious.
After a few minutes, I could feel her sort of nuzzling her back against me. She must have thought I was asleep, because she took my arm and placed it over her. Once again, my hand was on her tummy, but as she did this, my finger had brushed against the side of her leg, and it was then that I knew she had taken her pajama bottoms off in the bathroom. I couldn't believe it! She must have been just as aroused as I was!
With my arm over her, she backed herself up against me, snuggling up. I didn't know what to do. I just kept pretending I was asleep. I kept up my snoring act, but I think she was still awake. With my hand on her stomach, I could feel her moving under the sheets. I realized that she was secretly unbuttoning her pajama top. I knew for sure when I felt the fabric get gently tugged from under my hand, and my fingers found themselves touching the bare skin on her stomach.
Over the course of the next few minutes, I kept my hand limp, and she squirmed her body around, gradually nudging my hand up over her breast. There were probably a billion thoughts running through my head at that very moment, but I stuck to my act and pretended to sleep. Before I knew it, her hand was on top of mine, and she began to lightly squeeze it, so that my hand would squeeze her breast. She did this a few times, and then eventually eased up. Following her lead, I continued to squeeze it, all the while making my snoring sounds. She never suspected I was awake.
As my hands blindly groped her chest, my fingers fumbled around her nipples. I didn't want her to think I was too aware of what was going on. I could hear light sighs coming from her lips, and it sent shivers through my entire body like nothing else ever has.
With my eyes closed, and the covers over both of us, it was hard to tell exactly what was going on, but when I heard the sound of fabric being rubbed, I immediately knew what Kelly was doing. She had worked her hand down between her legs as was masturbating through her panties. This went on for several minutes, and I almost came from the thought of it!
Just like before, she began to nudge my hand, but this time, downwards. She subtly guided it down her body, so as not to "wake me up". I knew exactly what she was doing, so I played along. With my limp hand on the front of her panties, she guided my fingers down between her legs. When I felt how completely SOAKED her panties had gotten, I almost gasped out loud! They were just... soooooo wet!
Now, as a point of reference, since that time, I've had sex with about 8 or 9 other girls. All girls are different... some girls get very wet, some don't. There have been occasions where I've gotten very wet myself. I even had one very experienced boyfriend tell me that I was the wettest girl he was ever with. But believe me when I tell you, Kelly was in an ENTIRELY different league of wetness. Her panties where just so slippery, and absolutely drenched... from the crotch halfway up the front!
Just like with her breast, she pressed my fingers against her panties a few times, until I began to do it on my own. When she moved her hand away, I pretended to fumble around down there. I wanted to appear as "asleep" as I could. My fingers glided across the surface of the panties as I pressed firmly against her clit. I could actually feel it through the fabric now, and as I massaged it, Kelly bucked her hips to put more pressure on the area. As much as I wanted to slide my fingers in her panties, I didn't want to be too obvious.
My patience paid off. She nudged my hand up to her stomach, and I thought that was the end of it, but I felt her lift her body up and slide her panties down. I think she only slid them a few inches down her thighs, but that was enough. Kelly nudged my hand back down, and my fingers worked their way through the soaked bush between her legs. It was then that I realized she didn't trim herself, but I didn't care. It felt wonderful! I rubbed her bare clit like the world was about to end. As she bucked her hips, I moved my hand down deeper between her legs.
Before I could stop myself, I plunged a finger inside of her. Within about 2 seconds, I could sense her body tense up. I think this was the moment she had her orgasm. She held her breath for about 15 seconds, while my finger went in and out of her. As her muscles relaxed, she immediately moved my hand away from her. I guess she was too sensitive.
As I lay there, still pretending to sleep, I could tell she was pulling her panties back up and buttoning her pajama top. After a few more minutes, she got up and went to the bathroom again. Since I was so close to orgasm, I quickly made myself cum while I licked Kelly's syrup off my fingers. I would rank that in the top 3 orgasms I've ever had in my life. By the time she came back, her pajama bottoms where on, and I was rolled over, "asleep".
When we woke up the next morning, neither of us said a word about it. And that was it. It never happened again. To this day, I'm convinced that she thought I was sleeping the whole time.
After we graduated, we went to different colleges. We saw each other during summer and breaks, but after college, she moved to the Midwest and we kind of lost touch.
Regardless, nothing can shake the memory I have of that night. I don't know why I didn't pursue her more after that. Maybe because I don't think either of us was ready for that kind of relationship. Who knows. All I know is that I feel better after getting this off my chest.
If there is anyone out there that has been through a similar experience, I would love to hear from you, so I don't feel like I'm the only one that's ever tried something like this. I think Kelly and I both enjoyed what happened that night, so I guess that's all that matters.
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