This is one I've never shared before, with anyone who knows me. To be fair, it's not as though anything illegal or truly “rapey” happened, but this story was initiated without my actual consent, as you'll find out. I'm posting anonymously as it's not something I'd ever share with my sister (whom we'll refer to as "M")…or want her to find out on her own (we're very close and quite forward with one another, and I feel like she'd be offended that I never told her about it, awkward as the conversation might have been to have with her). Also, this is not a short story, so if patience or reading a multiple page story are not your cup of tea, you might be better served finding a two paragraph, most likely fictional “story.” And one last disclaimer, this is no work of fiction. All is absolutely true, and was ultimately a very formative experience for me in my own sensual awakening.
It was around 2003 or '04. I'd just broken off a long-term relationship with a girl I'd been with for just shy of 4 years, and we'd been living together almost a year and a half. I was 24 years old at the time. Not to go too deep into detail, but suffice it to say time showed we were not truly compatible, and wanted different things. Truth be told, she'd been “mapping out our future” without even considering my opinions and future wants/desires, and as I made it more and more known that I also wished to have a say in the trajectory of my life, the relationship started to crumble. Though she was never “dominant” of me inside or outside the bedroom, it seemed as though she wished to be the decision maker and saw me as the type who'd “go with the flow.” While a respectful gentleman, I in no way have ever had the desire to control or dominate a partner, nor be the submissive party to one who's controlling or dominant. As another (the last--I promise!) disclaimer though: this isn't a story about being or becoming a Dom, for all you kinksters out there. But it was indeed a journey that did lead me to find confidence and, strangely enough, comfort in taking the “lead” in intimate scenarios.
After the break up, I moved back in to my parents' house, basically moving into the open family room downstairs in our house and making it “my room.” Not a basement room, but rather literally the big entertaining area on the main floor of the house which you'd walk directly into upon entering the front door. Not much for privacy, but I had little intentions of staying for very long.
Well, it ended up being longer than I'd expected, and about 6 months later strange occurrences started taking place. At the time, I thought I was going through a “second puberty” or something to that effect, as my libido had seemed to get away from me and I began seemingly having very “adolescent” issues regarding my state upon waking a few mornings. I had a futon; a metal, uncomfortable thing with a mattress that was 5 years beyond being acceptably pillow-like and soft. It became so flat and dead it basically felt like I was sleeping on metal rails, and I rarely got restful sleep on that thing. So over time, I basically commandeered the couch in the family room as my unofficial bed. Not the greatest place to catch some Z's, but infinitely better than that damn futon!
I ordinarily am a heavy sleeper as is, and at the time I was working quite hard during the day/early evening and then smoking my brains out after work most nights. The devil's lettuce and I always got along swimmingly, hahaha. But as I preferred the more exotic, “knock-out” types of bud, I tended to be pretty well dead to the world while I slept. It had been some time since I'd been intimate with anyone, as I'd decided I'd abstain from random sexual escapades and would wait until I actually felt a genuine connection with someone before "giving it up" again. Needless to say, this left me insatiably horny most of the time, but through transcendental meditation (and fair share of self pleasure) I curbed my urges to a good extent. Then, there were a few mornings (or sometimes early afternoons) where I awoke to find myself having ejaculated whilst I slept. Something that had never happened to me when I WAS actually going through puberty, so I was bewildered but chalked it up to not "getting off" often enough as it were. I decided to cut out the weed for a little while, wondering if by chance it was happening because I was out so deep every night. My rationale was that perhaps my imagination was going into some sort of sexual overdrive when I hit REM sleep. If I was having sexually charged dreams, I was never waking with the realization that I'd been having them.
A few weeks later I did notice that while still a heavy sleeper, my dreams were becoming much more clear and vivid. And some of them were indeed quite sexual. A few mornings I did wake to find myself stuck fast to my thigh or, on one instance I recall well, I had come out of the little flap in the front of my pajama pants and was quite literally "sex glued" to the fabric. I concluded that my dreams were indeed apparently so erotically charged that I was finishing in the flesh when I was dreaming about climaxing.
Then one "night," I had an immensely intense dream. Some random girl was giving me just the most mind-blowing oral sex I'd ever received. The dream was so vivid and clear, I could literally feel the pressure rising in my core, and had one of those moments where I could "feel" her taking me all the way in, her nose lightly bumping over and over into my pubis. No one had ever done that to me before during fellatio. I came, and I came hard.
I remember slowly opening my eyes, with the fog of sleep still heavy in them. What my eyes took in was not me having had a traditional wet dream at all; my sister's fairly recently-legal and fellow high school senior best friend, we'll call her T, had her little hand wrapped firmly around the base of my manhood, and had me fully engulfed. It was HER nose that I'd felt repeatedly pressing against me during the tail-end of my dream! As I could see only the top of her head, and she obviously was unaware I'd woken at all, I simply closed my eyes and feigned sleep. Still twitching and pulsating from my orgasm, I could hear the slightest little moan of satisfaction come from her as I felt her ease back off of me and stop right at the base of my helmet. She wrapped her lips around a little tighter and I heard the slightest low-volume "pop" made as she finished withdrawing me from her mouth. In my state of fake sleep, my mind swirled with thoughts of how long this had been going on and whether I would sort of confront her about this, or simply say nothing and "obliviously" enjoy my occasional morning releases.
Less than a minute or two later, I heard my sister heading down stairs saying "all ready, T?" To which T replied affirmatively. And that's when I realized that not only had this tiny little cutie been sucking me off in my sleep, she'd apparently also been swallowing my c*m. I immediately knew she didn't always do this, as evidenced by the mornings I woke up to a bit of a mess...but irregardless, I was incredibly turned on by not only her adventurous naughtiness, but also her being forward and daring enough to just go after "it." For those reasons, I decided to play it cool at least for a little while. I certainly was not going to complain about being regularly serviced by this newly discovered sexpot.
Now, for some background info on T. She grew up the next street over from us, and she and my sister had been best friends pretty much since they started school and rode the bus together. I watched her grow up through pretty much her entire childhood, minus the 18 months or so while I was living with my ex. Admittedly, I was "too serious" about our relationship to keep close enough ties with my parents and siblings...you know, the codependency evident in most young adults' relationships that we're completely blind to while we're in them. Well, in that short time, T had certainly changed, physically at the very least. When she was younger, she was a very tiny and skinny little thing, and quite tomboyish. Same went for my sister.
My sister hit puberty fairly early, and started to look much like the young woman she'd become. T, well, not so much. She stayed very short, very thin, and very childlike in appearance pretty much up until I'd moved out to live with my ex. By that point they were both 16, and my sis had already gone through her growth spurt and had been fully "budded" for a few years, whereas T still looked like she were 10. Maybe 4'6" and couldn't have been more than 70 pounds. No sign of the "feminine mystique" settling in for her at that point in time. I honestly hadn't taken notice to her stunted physical maturation pretty much until that point, as for the few years prior they had both gone through a goth/emo phase. Lots of black, loose fitting clothing and no shortage of flannel and Doc Marten's. But now, being of driving age and moving into the middle part of high school, they'd both begun dressing far more feminately, with their intent obviously being to catch the attention of boys. While T was still lagging behind in the "curves" department, I did take note as to how her facial features had changed from the cherubic softness of childhood, and had become much more angular, defined and pronounced. Her eyes had become big, brown and beautifully doe-like. Very expressive, as it were. It was then for the first time that I subconsciously acknowledged that she was certainly going to be a stunningly beautful young woman someday.
Fast forward to my moving back home, and the first time really seeing T since then. I'd worked a rare early shift at work, and got home around 4:00 PM or so. The girls were hanging out upstairs in our living room, and when I got to the top of the steps my sister came running over, calling me by my nickname and coming in for a hug.
"Hey T, our big bro's home. Come say hi," she jubilantly exclaimed (as only having an older sister, T and my sis had been referring to my brother and I as her brothers as far back as I could remember).
I was admittedly, though I'd like to think not obvious to her, stunned by the vision heading towards me from across the room. T was still very, very tiny...not quite 5' tall, and still quite thin, but her maturation was undeniably on display. A tiny mid-thigh pleated skirt framed long, smoothly shining and toned legs leading into a pair of very cute and simple white sneakers. A white tee showing just a hint of midriff gave notice to a pierced bellybutton, and a flat, muscular stomach. Her beautiful doe eyes were done up in slightly smokey black eyeshadow, and her traditionally bob-cut hair was now long, dark and wildly wavy. Her now pouty, full lips being brought to one's attention by the light gleam of the clear lip balm she wore. And the most surprising thing to me was how she'd gone from barely having "mosquito bites" for a chest to now having an undeniably lovely pair of full, large breasts. Not huge, but quite big for her very petite frame (I immediately estimated they had to be C cups). When she came in and wrapped her arms around me, pressing herself into me, it became obvious that this was most likely an accurate guess and not trickery involving a padded bra or anything like that. I could feel their firm fullness pushing into my upper abdominal muscles as she hugged me tightly.
Far from seeing her as anything other than a younger "adopted" sister until now, I still simply pushed away thoughts of any attraction to her newfound look as a natural response, and was happy that this awkward late bloomer had come into her own. She had absolutely turned into the complete stunner I'd realized she could be those couple years before. And she seemed happy, confident, and fully aware of her being very pleasing to the eye. Things stayed this way in my mind, and despite my constant horniness and single status, I'd not even thought of her during self-pleasure time due to still somewhat seeing her as my sister's awkward, tomboyish little friend, and I as her unofficial big brother. Up until that fateful morning, that is.
For the next few weeks, I played it cool and acted asleep when I wasn't so zonked out, even with coming to realize her playing with me was becoming a nearly daily routine. Sometimes I was too out cold to know anything was going on, but other times I was somewhere between sleeping and awake and was acutely aware she was pleasuring me. I came to conclude that she would get to our place a little earlier than my sister would be ready by, and waited in the downstairs area where I stayed (we had a TV and our computer down there, so I'm sure my sister never gave it a second thought. I also deduced that it seemed the more time she had, the more daring she would be. With a lengthy window, she seemed inclined to orally pleasure me, while other times she simply squeezed, massaged and stroked me with her hands. Not always to completion, admittedly to my chagrin those times I was aware enough to feel what was going on, but almost every single morning during the week...as far as I could make out, and the often leftover evidence reinforced my deductions when I was too out cold to be aware. I was content with playing blissfully unaware, until one day in November of that year.
The morning started with my coming to and feeling the warmth of her mouth enveloping me. I don't know how long she'd already been at it, but she had to have arrived early that day. As I lay there, eyes clamped closed, every little movement and sensation she delivered were simply sublime. She would take me all the way in, then slowly make her way back off of me. Swirled her tongue around the head and then lightly traced the outline where the shaft meets the head. Kissing all around and up the shaft, then flicking her tongue ever so lightly at the tip. Gently and sweetly blowing air on my saturated member, causing great sensitivity and even more engorgement. Then repeating the process by gently popping me back into her tiny mouth.
This continued on for a good 15 to 20 minutes before I could feel my impending climax, coming along despite my attempts to delay the inevitable for more personal enjoyment. Then, as I erupted into her mouth, I could again just barely hear an audible moan and feel her taking every last drop of me. I was amazed not only at her very thorough and capable skills, but also by how whisper quiet she was as she did this. I mean my sister was most surely in the upstairs bathroom getting ready for school on these occasions, but T took special care to be sure she became none the wiser. After hearing them depart for their day, I got up and decided that I was not going to allow this to continue on without her knowing I was fully aware of what a naughty little thing she'd been lately. Tomorrow, I told myself, will be the day she gets her own surprise in the morning.
While my mind was mostly made up, I did still have some admitted hesitation about this. Except later that day, after working another early shift, I came home just as the girls were heading out to hang out with some friends, or go shopping, etc. As they went to leave, M said bye to me as T trailed behind her towards the door. She had on this adorable little sundress (it was a warm November afternoon during an Indian summer), and said bye to me as she reached the door, twirling around to close it and very coyly giving me a barely noticeable wink and blew a kiss my way. As she twirled in one motion towards the door and then back towards the outdoors, the bottom of her dress lifted up just enough that I caught an unmistakable glimpse of her bare bottom. Either this girl was wearing very small and barely there panties, or she was wearing none at all.
At this point I must confess that I have always had a weakness for ladies in skirts and dresses, and even greater weakness when there is nothing paired beneath said dress. Basically, I find the ease of access, along with the slightly taboo playfulness of going sans underwear, to be an irresistible combination. In large part this is why I've never been much of a fan of wearing underwear myself. Yes, I was indeed going to proceed with my plan.
So the next morning, after staying awake the vast majority of the night, I waited until right around when my sister's alarm would go off and then "went to sleep." Like clockwork, about a half hour before they'd normally head out, I heard the front door open and T walk in. Hearing her call to my sis, and her response of "I'll be down in twenty or so," I hoped she would be emboldened to go for her morning "snack." She did not disappoint.
I felt the thin bedsheet I'd used slowly start to be lifted up and pushed towards the back of the couch, until I could tell my lower half was no longer under cover. I'd made sure that I was "out" of my pajamas before she'd arrived, and the impending excitement of her arrival and my plan had me more than a bit "swollen" in anticipation. While not erect, I was nonetheless showing, with very little growing needing to be done to become full mast. I'm not going to embellish and talk of how "huge" I am, because that's not accurate. I'm self aware and comfortable enough with myself to know that I'm no John Holmes by any stretch, but that I am definitely adequately equipped and am quite confident in using what I've been blessed with when it comes to pleasure. Not to mention, I ordinarily get off more satisfactorily by getting my partner off, which no lover I've ever had has complained about.
Feeling her hands work around my legs, and then tracing their way up my thighs, I could feel myself begin twitching and pulsating as arousal fully took over. Before I knew it, there was the little hand wrapping around me, and the slow licks and kisses exploring my hardening manhood. I lay there enjoying every second of her efforts and affections, and allowed her to do her remarkably adept "thing." All things considered, it didn't take me all that long to be knocking on the door of an intense orgasm...this girl and the "inappropriate" nature of what was going on had me more turned on than I'd ever been before in my life. I came, and I came intensely yet again. She'd also once again had me all the way in her mouth when I did, and so I very casually opened my eyes and took in the sight of her completely down around the base of me.
Wild, wavy hair had fallen in front of her and was lightly resting on my stomach. I was just barely able to make out the contrast of the pink hue of her beautiful lips against the slightly darker tone of my still twitching and pulsating hardness, due to the slight part in her hair. It was as erotic a moment that I'd experienced in my relatively young life to that point. As she slowly began her ascent, going teasingly slow, I focused my gaze on her. Once she reached the top of me, my attentions still fully entrenched with her lips, I saw her just barely (and unintentionally sultrily) open her eyes and glance towards what I'm sure she expected to see: a very satisfied but dead-to-the-world asleep me. But rather, I lay there with my intense gaze and side-mouthed grin fixed on her.
Her eyes went from mere slits, to me seeing those big, lovely doey eyes open wide...and form into the "deer in headlights" look of someone who's been caught doing something they shouldn't. If it weren't for her still having me partially inside her mouth, I think she might've let out a scream or yelp due to her shock and surprise at seeing a fully awake me looking intentfully into her eyes. Rather, upon hearing my sister say "I'll be down in a minute or two," I simply gave T the international sign to "shhh" by placing my index finger vertically over my lips. Upon releasing me from her mouth's grasp, her eyes fluttered a bit and she lowered her head a ways with a bit of a bashful look washing over her. But, an unmistakably small grin formed along those pretty lips of hers as she lowered her head.
I quickly stuffed my now semi-relaxed c*** back into my pajamas and proceeded to get up from the couch, never taking my eyes away from her... and all the while she looked at me and then down repeatedly until I began to move past her. I could hear the low rumbling of my sister beginning to make her way to the stairs. T was again in a little dress, this one a bit tighter than a sun dress, but flaring slightly at the bottom. A flirty but functional little black dress, or LBD as the ladies like to refer to them, showing just enough of a hint of cleavage to drive men's (and ladies') imaginations wild. As I passed and made my way towards the downstairs bathroom, I placed my hand on her hip, leaned in and planted a silent but sweet kiss on her forehead, while artfully reaching my other hand back and up under her dress, lightly grabbing the tight little buttocks hidden beneath. Breaking our contact and continuing towards the restroom, she looked at me with a bit of pleading in her eyes, as if to convey to me her embarrassment. I again made the "shhh" sign to her, and gave her a coy wink.
All I could think about at that point was that there were no panties that met my hand on her cheek, nor did I feel a panty line when I rested my hand on her hip.
There's more to the story, and our little playful dynamic, that continues beyond this recounting. It also gives quite a bit of exposition as to her motivations and rationale. If you've enjoyed this answer, I would be happy to share more in the future...that is, of course, if you care to believe this to be the truth. It is, but I'd rather not bore any of you with more to read if you doubt the authenticity of my experience.
But that is the origin of my most inappropriate interaction with one of my sister's friends, by far. I didn't try to present this as erotica, yet I have nothing but fondness for the memory, and for T. So in writing this, I felt I should express it in the closest way to the way I feel about it all. Which is with genuine love and appreciation, and so it comes across as quite "romanticized."
Stay true, my friends.