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Two Tantalizing Tomboys

Category: Group Sex
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My roommate, Rob, was out of town that weekend, but that didn’t stop me from hanging out with Rob. There was another Rob that we hung out with pretty frequently and I ended up going out with him and Hugh that Saturday night. After a few hours at the bars, drinking a number of beers but failing miserably with the women, Hugh headed home and Rob and I headed to his house to crash.

Rob and his older sister, Carolyn, still lived with their parents, which made sense since the house was so damn big and it was rent-free. They also had a really choice guest room.

It was a cold winter night, so it was nice to see the big down comforter topping the queen-sized bed in the guest room. I stripped down to my birthday suit, dropping my clothes to the floor on the side of the bed away from the door, and climbed under the covers. I think I was out as soon as my head hit the pillow. I had no idea how much time had passed when I was awakened by a light in the room. Squinting toward the source, I saw Terri, one of Carolyn’s friends, looking back at me, holding a shirt in front of her. She got a naughty look on her face as she realized who I was laying there, and lowered the shirt to reveal that she was wearing only a bra and panties while asking what I was wearing under the covers. When I groggily told her that I had on less than she did, she asked if I would be willing to share the bed if she was willing to lose her lingerie. I was already stiff under the covers, concealed by the thickness of the comforter, so I eagerly agreed.

I’d known Terri back in high school and had wondered about her sexual preferences because she was very tomboyish. The fact that she was good friends with Carolyn, who was also very tomboyish, didn’t help to clear things up, either. As she reached behind her back to unclasp her bra, releasing a pair of pretty incredible tits, I was pretty sure that she wasn’t a lesbian, at least not full-fledged. I had never paid much attention to Terri’s physique, partly because she seemed to dress in loose, not very flattering clothing, so I was pleasantly surprised not only by her large tits, but by her flat abs as well. The sexy bra and matching bikini panties were also a definite contrast to her rugby shirt and cargo pants.

She slid her panties off her hips, letting them slide down her legs as I admired her light brown bush, before lifting the covers and climbing into bed. We met near the middle of the bed, each reaching out to find the other’s bare flesh. I could taste alcohol on her breath, as I’m sure she also could on mine, as my hand slid down over her hip and around to her ass. Her hand found my ass as well while mine moved up to her substantial tits as we made out passionately. When her hand found my rigid cock, she pulled away from me and breathlessly asked me if I had a condom. I told her I did, in my wallet, and she told me to get it because she wanted me inside her. I rolled toward the side of the bed, found my jeans on the floor and quickly had my wallet and the condom out. I tore open the package and rolled the latex over my tool as I moved back over to Terri. Her hand found my latex-encased cock and was already pulling me toward her waiting pussy as I moved over her. As she guided me to my target, I pushed my hips forward and slid easily into her hot, slick pussy. We both groaned as I penetrated her, pausing once my full length slid completely into her.

As I slowly started pumping in and out of her, I brought my lips down on Terri’s, her mouth immediately opening to admit my tongue. Her pussy felt amazing as my cock slid in and out and I was incredibly turned on to be fucking and making out with her. Terri was raising her hips to meet each of my thrusts and soon my slow, rhythmic lovemaking picked up in pace to more frantic fucking. Despite being incredibly fired up, I didn’t feel as though I would be cumming too soon; on the contrary, I felt as though I could fuck Terri all night. Terri seemed to be enjoying it, too, based on the sounds that were escaping her mouth only to be muffled by my own. When she finally broke our liplock, she asked if she could be on top. I think I said, “Hell yeah” before flopping over onto my back. I was glad she’d left the small bedside lamp on because looking up at her as she mounted me was a vision I wouldn’t want to have missed.

She swung her leg over me and reached down to guide my erect cock to her pussy. As she lowered herself onto me, I think I enjoyed watching my cock disappear into her light brown bush as much as I enjoyed the feeling of her hot, wet pussy. As she started moving up and down, my gaze moved upward. I was impressed to see the definition in her abs each time they contracted as she fucked me. Looking slightly higher, I admired the large, pink aureoles surrounding her hard nipples atop her big, bouncing breasts. I was hypnotized watching her tits bounce while enjoying the feel of her pussy sliding up and down. A sort of gasping moan eventually broke my trance, causing me to look up at Terri’s face. The look on her face at that moment could only be described as rapture. The color was high in her cheeks and with each panting breath, she let out a little moan. The moans seemed to be getting closer together as I could feel the pace of her riding me picking up. I brought my hands up to play with her bouncing tits as she got closer to orgasm, brushing my thumbs over her erect nipples. Finally, Terri stopped moving and a shudder seemed to pass through her as she let out a shaky breath.

I was watching Terri’s face, my hands now on her hips, as she blinked rapidly and seemed to become more aware of where she was. She smiled and swung her leg over, my cock popping free as she dismounted me. I panicked for a moment, thinking she was done with me, before she lowered her face to the pillow next to mine, still remaining on her knees.

“Doggie-style, please,” was all she said before I was up and moving around behind her, my cock waving in front of me. I hadn’t had a look at her ass yet so I admired it briefly before guiding my cock back into her still hot and slippery pussy. I started out holding her hips and pumping my cock rapidly in and out of her but soon leaned forward to fondle her fantastic breasts. As I held her hefty melons in my hands, gently brushing her nipples, I was humping my hips against her muscular ass. I slipped one of my hands down over her flat stomach and between her legs, seeking out her clit. Finding it, I stroked it in time with my cock pumping in and out of her pussy. The alcohol, fatigue and thin layer of latex could only help my staying power so much in the face of such a snug, slick, hot pussy so it wasn’t much longer before I could feel my own orgasm finally coming on. Straightening up, I grabbed Terri by the hips again and began fucking her harder, my hips slapping against her ass. I watched as one of Terri’s arms moved from up around her head to underneath her, presumably so that her hand could replace mine on her clit.

She’d already orgasmed once, so I wasn’t too concerned about her keeping up with me; I was at the point where I just wanted to cum. I was really enjoying her pussy, making the most of it in case I never found myself in this position again. Terri was pushing back against my incoming thrusts and letting out little moans again. When I was just seconds away from blowing my load, Terri let out a soft cry and I started to feel little tremors around my cock. That did it for me and I let loose, shooting my wad into the reservoir tip. Once I was finally spent, I pulled out and flopped on the bed next to Terri.

Instead of lying next to me, Terri straightened up on her knees again and slipped the condom off my shrinking cock. Offering to take care of it, she moved to the edge of the bed and stepped off. I was still warm from the activity, so I didn’t pull the covers back up, just admired her nude form as she left the room. I was surprised that she hadn’t at least covered herself with something since we weren’t the only ones there, but started to doze before I had much time to think about it.

Terri filled me in later on what had happened when she’d left the room. Her immediate destination actually had not been the bathroom, but Carolyn’s bedroom. She went in and turned on the bedside light, waking Carolyn up and, waving the used condom before her, sang, “Guess who just go laid…” Carolyn was awake quickly listening to Terri’s story of finding me in the guest bed and the ensuing activity. Terri claims that Carolyn then said she wanted to get laid, too, so Terri suggested that I probably would not mind if she brought Carolyn back with her. She disposed of the condom while Carolyn grabbed a couple of unused ones from her nightstand, then they both returned to the guest room to find me snoozing. Instead of just leaving me to rest, they closed and locked the door, then took position on their knees on either side of me. I woke up at about the time I first felt lips and a warm mouth wrapping around my cock.

Blinking the sleep from my eyes, I thought I must be seeing double realizing that there were two women taking turns sucking my cock. Terri noticed I was awake and came up to kiss me and explain that Carolyn was horny and asking if I’d mind fucking her, too. I said that I would if I could eat Terri’s pussy at the same time. Terri got that devilish look on her face again asked Carolyn if she was ready to get fucked. She slid my cock from her mouth and it looked (and felt) as rigid as it could possibly get. Carolyn produced a condom, slipped it onto me then moved into position above me, straddling my hips. She was thin like a runner, with small, perky tits topped with hard nipples. Her short hair was naturally reddish, as proven by the neat bush topping her pussy. As she settled down onto my cock, her pussy feeling snug and slick like Terri’s had, Terri straddled my head, her pussy hovering above my face.

As I felt Carolyn starting to ride me, I raised my head and began to lick Terri’s pussy, tasting the juices that were flowing copiously. Other than Carolyn fucking me, I had no idea what else was going on above me as I devoured Terri’s sweet pussy and raised my hips up to push deeper into Carolyn. When I paused to readjust my position to allow me to finger Terri’s pussy while eating it, I took the opportunity to peek out from under Terri to see if I was missing anything. Imagine my surprise when I saw Carolyn’s hand on Terri’s tit, Terri’s fingers on Carolyn’s clit and the two of them seriously sucking face. I didn’t think it possible, but I felt my cock swell even bigger. I went back to working on Terri’s pussy with a vengeance, fingering her while licking and sucking her clit. My renewed effort and enhanced cock seemed to have an immediate effect on both of them as I could hear them now moaning into each other’s mouths. I kept at it, enjoying the taste of Terri’s pussy and the feel of Carolyn’s sliding up and down my shaft. I felt Terri beginning to shudder above me and was rewarded with a fresh flow of pungent juices. Before she finished cumming, I felt Carolyn slam herself down on me and experience a prolonged shudder herself.

When she’d finished cumming, Terri removed herself from my face and suggested to a flushed and sweaty Carolyn that she try it doggie-style. Though dazed, Carolyn seemed to be into the idea and swung her leg over me, my rigid cock popping free of her pussy. I sat up and maneuvered onto my knees, delaying Carolyn from getting into position so that I could kiss her first. As my tongue entered her mouth, I took her ass in both hands, letting go only when we stopped kissing. I turned to Terri and made out with her, too, putting one hand on her ass and moving the other back onto Carolyn’s. When I broke off our kiss, I said, “Now you two,” indicating that it was their turn to kiss. They went ahead and made out as I felt up their asses.

Carolyn finally stopped and said she was ready for more fucking, moving into position and lowering her head. I got behind her and guided my cock back into her, loving the snug feel of her pussy. Terri was kneeling beside me so that we could make out and she could feel Carolyn’s ass while I fucked her. I had one hand resting on Carolyn’s lower back and one grasping Terri’s ass while I pumped my cock in and out of Carolyn’s hot pussy and my tongue explored Terri’s mouth. Eventually, Terri moved away from me and positioned herself, legs akimbo, in front of Carolyn. I leaned forward over Carolyn, first playing with her small tits as I humped her ass, then slipping a hand back between her legs to play with her clit as I had when I’d been fucking Terri. Carolyn had both hands between Terri’s legs, spreading her pussy open and fingering her hole as she licked and sucked Terri’s clit like someone who had been there before and knew exactly what Terri liked.

I managed to get Carolyn’s knees out from under her so that she was lying flat on her stomach while I continued to fuck her and play with her clit. Carolyn continued to work on Terri’s pussy, which I was much closer to in this position. I was able to watch Carolyn’s talented tongue working on Terri’s clit and could feel the effect on my continuing arousal. Terri and Carolyn were both moaning again, so I was fucking Carolyn harder, wanting to cum as closely with them as possible. As it turned out, I started the chain reaction. Carolyn’s pussy felt so good as I was fucking her that I finally couldn’t hold out any longer and began to pump my load into the condom. Carolyn felt my cock twitching and spasming as I came and began to cum herself. As she moaned against Terri’s pussy, Terri experienced her own orgasm.

We lay there catching our breath for a minute before I slid out of and off of Carolyn, the night air cool against my sweaty stomach. Terri moved down onto Carolyn’s other side but Carolyn got up, taking my condom herself this time. I watched as she pulled on a robe that she’d apparently shed upon entering the room while Terri slid over closer to me. I don’t know how long Carolyn was gone because, by the time she came back, Terri and I were both asleep. I woke to sunlight starting to stream through the windows and found myself under the covers, snuggled between Terri and Carolyn.

The two of them began stirring at about the same time as me and we were soon touching each other again. They both wanted to get fucked but we didn’t think it would be safe to linger this way for too long, deciding that discovery by any of Carolyn’s family would probably be bad. My cock was rigid and ready to go, so Carolyn sought out another condom while I explained what we were going to do. As I rolled the condom down my shaft, Terri positioned herself on her back in the middle of the bed with a pillow under her ass. Carolyn then lay on top of Terri, positioning her pussy just above Terri’s. They immediately began to make out as I slid into Terri’s waiting pussy. Terri’s pussy felt great, but Carolyn’s was waiting, too, so after a dozen or so strokes, I pulled out and pushed into Carolyn. Carolyn’s pussy felt great, too, but I soon went back to Terri’s again. As I positioned myself to slide back into Terri, I could see that they each had a hand on the other’s clit and were working them vigorously as I alternated fucking them. I went back to my rhythm, fucking Terri for a while then switching to Carolyn and back again. Our initial concern had been with someone finding us, so we were trying to do all of this pretty quickly, but satisfying for all of us. Terri came first, at a point right after I’d pushed back into her, so I kept fucking her as long as she kept cumming. Her orgasm made her pussy feel even better, so I worried that Carolyn would be out of luck if I didn’t pull out of Terri soon. Luckily, as I pushed back into Carolyn, she started to cum, so I didn’t need to worry. As her pussy flooded with fresh juices and swelled with blood flow, that was it for me and I began to cum as well.

Once we were all spent, Carolyn slipped into her robe and recon-ed the hallway. Finding it safe and quiet, Terri collected her clothes and slipped out along with Carolyn. By the time I got dressed and headed downstairs, Carolyn already had a pot of coffee on and was starting breakfast. Rob and his parents eventually found their way to the kitchen, no doubt lured by the aroma of fresh coffee and bacon, and we all ate breakfast together, with no one the wiser that Carolyn, Terri and I had spent the night together.

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