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Our Sleepovers

Category: Lesbian Sex
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This is a memory of my first time with a good friend. It happened in the 1980s in a small town in California.

The first time I was with another girl was my senior year in high school, just after I’d turned 18. I was a bit of a late bloomer but by my senior year I’d finally started to fill out, get noticed by boys, and, I suppose, give myself permission to be interested in sex.

My boobs were small, an A cup at best for most of my first three years but by my senior year they’d grown into a solid B and my hips started to expand and I felt more comfortable in my own skin. I stood about 5’5 with shoulder length, dark brown hair. I was an athlete and in good shape and as my body matured, it was nice to feel like I fit in a bit more and that made me less self-conscious.

I learned how to masturbate just after my 18th birthday. I know—what took me so long! I guess I’d played around with myself before but had no clue what I was doing nor of what the ultimate outcome was supposed to be. My nipples have always been really sensitive and I can still remember the tingle that pinching them would give the rest of my body.

I eventually moved on to more than just my fingers and experimented with things like the back end of my hair brush and even the tip of a small banana one or twice. (I even once put a close pin on my nipples—which was also the time that I started to learn and get turned on at the fine line between pleasure and pain, but that’s another story!).

Caroline and I had been friends for a few months when we started hanging out more often and doing regular sleepovers. We’d met on the soccer team sophomore year but didn’t really become friends until we both became starters in our final year.

Also 18, she was short and really athletic, a fast runner with compact legs that led up to a tight butt that helped her to look amazing in soccer shorts and her bikini bottoms. Her chest was about the same size as mine (or maybe a bit bigger with a small C cup) and, also like me, she wore her dark hair down to her shoulders.

I guess you could describe both of us as “Plain Janes”—cute and petite brunettes with dark skin and brown eyes. We were ‘good girls’ who both did well in school and, at least most of the time, we did our best to follow the rules.

Neither of us were big drinkers and we spent a lot of weekends watching movies, eating yummy food, and talking about boys. We’d both kissed a few and had gone as far as third base but we were both virgins and didn’t feel any pressure to change that.

And after all these years, I can remember the question she asked that started it all.

“Do you ever think about giving someone a blowjob?” Caroline said one night after watching a movie while we lay in my full-sized bed together.

“I guess sometimes,” I answered back. “I almost gave Andy one in his car once but I chickened out. Why, do you?”

“I totally do,” she said almost immediately, with a sigh that was wrapped in a devious little smile. “I don’t know why…something about it just makes me want to do it.”

“I’d rather have a boy eat me out than me give him a blowjob,” I said to her.

“Yea, I like that thought, too,” she said, “but I really want to try it…geez I’m a slut!” she said laughing.

“Nooo, I get it,” I said to her, laughing back. “I liked giving Andy a hand-job and I totally wanted to put it in my mouth just to see what it was like but I just didn’t have the guts to lean over and do it.”

“Well if only you did have the guts you could tell me what it was actually like!” she laughed as she slapped her hand down on top of my comforter.

We laughed for another minute but kept talking about blowjobs and which boys we’d be willing to give one to and I remember suddenly noticing that our legs were touching under the sheets, though they had been since we got into the bed.

After about a minute of silence, it was my turn to ask a question.

“Do you masturbate?” I said, somewhat quietly to her.

“No. I mean, not really. Do you?”

“Sometimes,” I said back to her, only slightly embarrassed. “I get so horny sometimes that it’s hard not to…sometimes I just can’t help it.”

“I know,” said Caroline. “And I’m lying…I totally do it, like, a lot.”

“Omygod I do it all the time!” I said to her, somewhat relieved that I wasn’t the only one, as we laughed again together in that bed.

It was quiet again for a minute and I again noticed the warmth of her skin on my leg and felt her hips shift on the bed.

“What do you think about when you do it?” she asked me quietly, as we both continued to look at the ceiling that was lit up with the rest of my room by the light that I’d left on in the adjoining bathroom.

“Blowjobs!” I said as we both started laughing.

“Seriously,” Caroline giggled. “What do you think about?”

“I don’t know,” I answered. “Hands on me, I guess. Sometimes I think about what it’d be like to have sex. Sometimes I think about getting eaten out. Just the idea of being naked with someone is usually where it starts in my head. What do you think about?”

“The same stuff. I’ve liked it when I had my nipples sucked and I liked it when I’ve been fingered before. And, yes, the idea of giving someone a blowjob gets me going, too.”

Almost all of the sudden I noticed that I was getting turned on and that I was starting to get wet. I was both embarrassed and excited with that realization.

“OK so if we keep talking about this stuff I’m going to get more and more horny,” I announced in a somewhat sarcastic voice.

“Is that bad?” she said to me, turning her head away from the ceiling and towards me.

“No it’s not bad I just may have to put on new panties after a while,” I said to her with a laugh.

“I’m wet too, if it makes you feel any better,” she said through her grin.

“Ha!” I responded. And I’m only a little bit wet!”

“Then what if I told you that Andy was ready to suck your nipples and put his tongue all over them and kiss your neck and your stomach and then eat you out!”

“OK, definitely wetter now…what are you trying to do to me?” I said with a giggle.

“Well you said you were only a little wet so I was just trying to help,” she said with a smile of her own and a told-you-so tone.

Our thighs and knees were pushing together a bit harder now, as her leg bounced up and down in a nervous nonchalance next to mine.

“What else can I say to get you wetter?” Caroline asked me.

“Pretty much everything you’re already saying,” I said to her. “And if you weren’t here I’d definitely be masturbating by now!” I said with another laugh.

The room got quiet until Caroline said: “Why should me being here stop you?”

I paused.

“I don’t know?” I said back to her. “Is it weird if I wanted to? And I only would want to because of what you’ve been saying about sucking nipples and getting fingered!”

“Well…go ahead…you should do it if you want to,” she said, almost under her breath.

I waited a few seconds as I thought, as my mind raced with the idea of touching myself in my bed next to my friend Caroline.

“I will if you will,” I finally said to her, never taking my eyes off the ceiling.

“OK,” she said back to me after a second of quiet. “We’ve come this far and I’m too horny to say no,” she said into the air with another laugh.

I reached my right hand under the covers and pushed it down my body to my stomach and finally to the elastic of my panties. My hand slipped past as my index finger pushed its way across my vagina.

I heard Caroline suck her air in, as her fingers must have also found what they were looking for, while we both gently spread our legs into each other and pressed our hands into ourselves.

We were both mostly quiet and I could feel the bed trembling as we both slowly but deliberately rubbed ourselves.

After less than 30 seconds Caroline asked me, with a somewhat panted and deeper voice than I was used to hearing from her, what I was thinking about.

“Blowjobs and the fact that I’m masturbating in a bed next to another girl,” I said with an exhale and forced giggle.

She laughed a bit and said: “Me, too,” as she pushed the covers down past her chest. “It feels really good, though.”

“I know,” I said back, as I slid my left hand up my shirt and on to my right nipple that was hard and as sensitive as usual.

“Do you mind if I take my panties off?” she asked as she started to pull them off with a wiggle of her hips before I answered the question.

“Only if you don’t mind that I’m taking mine off, too,” I said, as my hand left my nipple and my thumbs went under the elastic at my hips and pulled my panties off in one quick motion.

I started to spread my legs again and our thighs pressed against each other and I pushed my knee underneath her thigh and our legs rested on top of each other.

“Is that ok?” I asked as my fingers found my bits and picked up where they’d left off. “It gives us more room…”

“Mmm-hmm,” she said back, followed up by “how do you do it?”

“Do what?” I asked as I continued with my index finger, as our legs draped across and pushed harder into each other.

“Rub yourself,” Caroline said, “how do you rub yourself”?

“With my index or middle finger, up and down,” I said in somewhat of a pant. “What do you do?”

“Circles,” she said with the same pant. “Two fingers and circles…and then I push a finger inside sometimes.”

“I haven’t done circles…does it feel good.”

“Really good…try it.”

And so I did. My index and pointy finger started to slowly make circles on my clit and I moaned almost immediately as my leg pushed further into Caroline on the bed.

“That didn’t take long-told you,” I heard her say with a smile.

“It feels amazing,” I said back. “How have I not been doing this?”

“It feels good but I didn’t realize it felt THAT good,” she said with another laugh.”

“I just have talented fingers, I guess,” I said to her with a smile as I turned my head towards her and she turned her head towards mine. “Ah…circle, circle, drag. That feels really good, too,” I said.

We kept our eyes on each other, with our faces just over a foot away as we continued to masturbate together.

“What do you mean ‘circle, circle, drag’?” she said, not taking her eyes off of mine.

“Fast circles with your middle finger and then a slow drag across,” I said to her.

She looked at me with a blank expression.

“Show me,” Caroline said, as her eyes narrowed on me and as that devious smirk swept across her face.

“Show you how?” I asked back with a smile of my own. “Like pull down the covers and watch me do it ‘show you’?”

Another pause.

“No…I mean show me like this,” she said as her damp fingers touched my left wrist and wrapped it with her hand, tugging at my arm and pulling it from my vagina towards her own. “Show me on me.”

I resisted at first but then I let her bring my hand closer to her, as she set it on top of her thigh, let go of my wrist, and again whispered “show me,” as her eyes narrowed further onto mine.

“Really?’ I said, just as quietly. “Should I?”

“We’ve come this far…” she said, as I felt her fingers brush against the top of my thigh, as the tips of them slowly and shakily stroked against my skin.

I remember being unsure, with my hand resting very lightly on the top of her thigh and my instinct was to pull it away. But I was so turned on and so wet that the idea of her touching me was too much to ignore and I knew that I wanted it to happen. I started to move my fingers and hand down towards the inside of her thigh, turning my body slightly towards her, as her hand moved further against me and as she more deliberately moved it down and I felt her fingers graze the top of my pubic line.

“Show me, Beth,” she said again, smiling at me with what to this day is the most erotic expression I’ve ever seen on another person, as I felt her middle finger move gently across my pubic hair, to my clit and further down so that her entire hand was covering my bits and her fingers were gently sweeping across my vagina.

My breath automatically exhaled and my knees pushed further out as her fingers started to move harder and more deliberately on me, as I let my hand slowly fall down the inside of her legs, down her thigh and to the top of her vagina. She had thicker pubic hair like I did and we were both equally wet with excitement, as our fingers began doing circles and drags across each other’s vagina.

“Oh wow,” she said as I watched her eyes close. “That feels really good…I like the circle-drag thing…please keep doing that”

“I like how you’re doing it, too,” I said back in between breaths. “You’re really good at it…and you’d better not stop, either.”

We both spread our legs further into each other and fully committed our hands and fingers to what we’d decided to do. We were both breathing heavily, both moaning and ‘ah-ing’ and letting out quiet ‘uhs’ from our throats with each circle and touch and I finally sank my finger inside of her, as she let out a slow ‘yesssss’ and pushed her own middle finger inside of me. In and out we went, moving each of our fingers up and down and back and forth inside of the other.

After a few minutes of this mutual masturbation Caroline turned to me again and whispered “will you suck my nipples…?” through her lust filled eyes and I slowly, yet shyly, shook my head yes, as she pulled her fingers out of me and leaned forward to pull her t-shirt off while I kept my fingers inside of her.

Her light pink nipples were sticking out and they were long, pointing towards the ceiling with energy and excitement as her back went back down to the bed, while she tugged at the bottom of my shirt up and asked me to take it off, too. I pulled my fingers from her and took it off, dropping it off the side of the bed as we turned our naked bodies to each other and leaned to pull ourselves in closer.

And I didn’t mean to do it but when we turned to face each other I automatically leaned my face towards her and our lips met, gently and somewhat awkwardly at first as we both started to resist what I’d done—but then we relaxed and pressed towards each other more intentionally, as we committed to it and gave into the desire, as our mouths opened and our tongues met and twisted and licked each other in a passionate kiss that lasted for a few minutes.

Caroline leaned her head back and I kissed my way down to her chin and then to her neck, draping half of my body across hers as I started to crawl on top of her and I finally stopped at her collarbone, lightly kissing it with my lips, pressing into her skin, and finally finished by running my tongue the length of her collarbone to her shoulder blade.

Her hands were smoothing the back of my own shoulders and one cupped the back of my neck with her fingers, as she used her other hand to run her other fingers through my hair, all the while letting out little sighs and moans as she hungrily fidgeted her hips under mine.

I could feel the heat and hair and wetness of our vaginas pressing together as I finally rolled entirely on top of her and as she spread her legs and wrapped them around me while my tongue pushed further into her mouth and our vaginas pressed together.

I pushed my pelvis into hers and we slipped across each other, moaning in our throats as we continued to kiss and as our wet vaginas slid and opened across and against each other. I pulled back from her and looked at her face that was now flushed and the lustful expression she carried was such a turn on.

I slid my boobs across hers as I licked down her neck again to her shoulders, moving my own chin towards her nipples, as I reached my hand up and put it on her chest, letting her erect nipple slide in between my index and middle finger and I pinched it and as her body tensed up.

I kissed down her chest, still with my pussy-soaked fingers on her boob, as I spread her own juices across her nipple while my tongue traveled down between them both and my mouth licked around every inch of her boob—without ever touching her nipple.

Finally I took her pointing nipple between my lips, like one might take a straw into their mouth to have a sip of something that they’d been looking forward to tasting.

“Mmmmm,” was all she could muster as I popped her nipple in and out of my mouth, licking and pressing it hard with the fat of my tongue and flicking it with the tip. “The feels amazing Beth…god…”

I continued to play with her left nipple while I sucked on her right one, finally moving my hand away from her chest as my lips moved over to the newly alone tit and I sucked it inside, feeling it grow tighter in my mouth.

My left hand went back down her body, to her thigh and then back to her vagina, as my index finger easily slid back inside of what was now her sopping wet pussy.

“Oooooohhhh,” was the long sound of the exhale that came from her stomach, as I gently nibbled and sucked her nipple and found her clit with my thumb. “I think you’re going to make me cum,” she said in almost panicked tone, “nobody but me has ever done that before…”

My pursed lips took her nipple in and out of my mouth with my tongue flicking against it each time it came back inside. My middle and ring finger pushed inside her pussy while my thumb rubbed her clit as her hips began to gyrate and as her body began to shake, while little cries starting slipping from her mouth.

I felt her try to hold her breath as she started to come, finally letting it go with her hips shaking and her vagina pulsating against my fingers. I kept at it with my lips and tongue on her nipple and her hips started pulling away from me as she shook harder, with my hand soaking wet and still going in and out of her with her arms finally reaching around my body to pull my face tight against her chest, as I heard her faintly squeal and pant.

“Omygoddddddddd,” she said quietly as she panted more and tapped her fingers on both hands across my back. “That was ah-mazing.”

“I’m glad you liked it,” I said with a smile and with my ear pushing into the skin of her chest.

“An orgasm feels so different when someone else gives it to you,” she said with a tone that sounded like a revelation. “Have you ever had that happen?”

“No,” I said back. “I’ve had them but only from myself.”

“Then you’re going to let me give you one,” Caroline said to me, lifting up her head as she began to slide my body off of hers.

“Um, OK,” I said somewhat sheepishly. “How?”

“You tell me…” she said, lifting her torso up onto her elbow and leaning her cheek into her hand. “I owe you now so I’ll pretty much do whatever you want me to.”

“Anything, huh?” I said with a smile. “I mean, since we’ve come this far…what if I asked you to eat me out?”

Caroline immediately smiled again and leaned her face towards my body, pushing the covers from my knees to the edge of the bed as she slid down my torso, pushing my right leg up from the thigh and spreading me open. Her chin went down to the top of my leg with her mouth dropping tiny little kisses down my thigh and I nervously inched myself up the bed, trying to guide my wet pussy to her mouth faster.

She pulled her head up from my thigh and put her hand just under my stomach, and finally down further to my pubic hair, with her face no more than four inches from my pussy. I watched her look at it, pulling her fingers through the hair and then back up, as I could feel myself opening each time she moved her hand across my skin.

Her eyes looked up my body to mine and we both gently smiled at each other.

“Ready?” she asked me.

I very barley shook my head yes as my toes curled in anticipation of something that I’d been fantasizing about for months.

She leaned her head forward and gently and just slightly kissed the top of my vagina, as electric charges shot through me and as I continued to watch her face in my mildly lit bedroom.

I felt her tongue gingerly make contact with me, and then it pushed harder against me, as her hands gripped the tops of my thighs and her lust escaped her lips in a moan and she leaned in closer and her full tongue licked slowly, from top to bottom, of my vagina.

My legs spread further open and met her moan with one of my own and then my eyes closed and my hands reached out, with my fingers gently stroking her hair and touching the top of her head.

With both of her hands she pushed both of my thighs and opened my legs even further, spreading me and opening my pussy wider in the process. Her tongue licked me up and down, sinking inside of me and then back out and then up to my clit, where she circled around it, gently flicking it and then pushing across it with the thick part of her mouth and tongue.

She was licking at an even pace and I could feel her breath on me, as I squirmed and bounced just a little on the bed and as I felt her finger run the length of my opening, finally finding its way inside of me and as her tongue went a bit more purposely on my clit.

“Right there, Caroline,” I managed to say through clenched teeth. “Keep doing that…that, that, that!” I said louder than I’d meant to as I felt my own body start to shake and my very first sex-induced orgasm growing from deep inside of me.

She used the tip of her tongue and flicked it on my clit, never losing contact with my bits as my orgasm started to come out, with my hips slowly beginning to shutter and a passionate and shaky cry quietly escaping from my lips.

“Uhuhuhuhuh,’ I said as one word as I began to come, as Caroline plunged a second finger inside of me and leaned in harder on my clit, taking me into her mouth with a fast tongue furiously lashing against me, pushing my thighs up even higher so that my butt started to life off of the bed, while I came in her mouth and while she rode my orgasm as my hips continued to arch and until it finally ended and I sank back into the bed.

When I finally finished shaking, Caroline lifted her wet and shiny face up from me and smiled that devious smile at me.

“How did I do?” she said as she pulled herself back up my body, wiping her face with her hand while I continued to catch my breath.

“You did good,” was all I could manage, and I felt my pussy throb and my legs still tingle from the most intense orgasm that I’d ever experienced. “It was better than I’d been hoping it would be.”

“Next time you’ll do it for me then?” she asked.

“Uh-huh,” I said, “I totally will.”

We lay there wrapped up in each other for a while longer and finally fell asleep after climbing back under the covers—but without putting any of our clothes back on. She kissed me on the cheek when we woke up that next morning and we made each other promise that it would be our secret.

We played around with each other a few more times (yes, I eventually returned the favor—and we even went a bit farther, though that’s likely another story) that year and always stayed friends, though we eventually lost contact with each other.

The great part was that it never got weird between us and neither of us “fell” for the other in a way that messed up our friendship. We continued to have those fun sleepovers (even when we eventually had boyfriends) and got pretty good at getting each other off.

We stayed true to and honored the fact that I was our little secret. And aside from sharing the details with my husband, this is the first time that I’ve ever told the story.

Looking back, it was an amazing few years of discovery for both of us and I have no regrets at all that it happened.

Nineteen years later, we recently connected again on Facebook and, who knows, maybe we’ll get to revisit that fond memory all over again at our 20-year high school reunion next summer!

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