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Double Penetration

After I graduated I rented a room from a gruff house builder called Jimmy. He was a good guy was Jimmy, in his mid-30s. Despite his relatively young age he’d been working 20 years already. Early on as a kid he never finished school and he was too temperamental to handle for any of the bosses at the jobs he did, so he set out on his own. By 19 he had his own small company employing high school drop-outs to clear hard rubble from building sites. By 21 he was employing licensed pros to help expand into roofing, then demolition, then building. With no education but a sense for numbers and a notorious temper for anyone who ripped him off, Jimmy developed a hardworking and honest business that by age 25 allowed him to design, build and own his own home.

As for me, my family lived further up the coast near college, I didn’t know too many people in the city. I first rented a room from Jimmy as temporary accommodation while I grunted away in a summer job for his rubble company one college break. Half way through those holidays my father grabbed my bicep and snorted. He said that rather than serve coffee in the local shop, I needed toughening up in hard labor. He saw Jimmy’s ad and applied for me. It was the roughest month of my life, I really did learn what hard work was. Jimmy told me straight that I’d gone from a wimp to a good worker over those four weeks and I’d never felt so proud.

A couple of years later we ran into each other in a coffee shop in the city. He was overseeing the fitting of a store next door, I had just come out of a final job interview with a design firm. Perhaps with one eye on his own future interests he offered to put me up until I found my own place in the city. I ended up staying 3 years.

Jimmy never married, but he always had good company, the most important of which was Sara M. Sara was younger, my age. She had small features but was strong. She had long, styled dark brown hair and a beautiful face, kind of Natalie Portman-ish; delicate but not fragile. She had a perceptive cleverness and she was polite with it. There was a look Sara had, as if she knew what you were going to say and do before you did it, but she let you finish anyway, not interrupting. It’s fair to say that Sara stood tall, even though she wasn’t. It helped that she was happy all the time, not much seemed to get her down. She was a nice person to have around.

Rarely did I see Sara in pants, it was always dresses or skirts. She was sexy in a young-professional-woman sort of way during the week, but on weekends those dresses and skirts were so short that her ass was covered most times by bare wisps of thread. I can’t imagine I would have felt comfortable if she was my girl. The way guys stared lustfully at so much inner thigh, me included, I would go stir crazy if she was my girlfriend.

I really don’t know how Jimmy and Sara met, she just started turning up more than the other girls until the other ones stopped coming. She stayed over on weekends but on weekdays she was kicked back to her own place. I never quite knew whose rule it was, but I suspect it was mutual. Sara was in a blue chip management consultancy, not long out of their graduate program. She worked as hard as Jimmy.

As for me, I never had too many girls. I wasn’t very good at opening lines. I needed someone to introduce me. I needed time to warm up. I usually lost my chance before my charm had started its motor. So when I was able to get onto a date, or into a girl’s bed, I had to make it stick. In consequence I spent longer than I should have with some incompatible matches, compromising and procrastinating for fear of being alone. Inevitably the end would come, much later than it should have.

There was one, though. Julie. She was nice. I felt natural around her, I was myself. Her mum let her stay over in my room and it was the first time that sex was a regular part of life for me. Most times Julie was the instigator. It was like my sperm gave her energy, her demand for it almost outstripped supply.

I thought we were going really well but then her dad got sick in Canada. She moved over there to be with him. I tried to keep up the long distance thing, flying over a few times. But we couldn’t keep it up. Eventually she drifted into other arms. I rang once on a Sunday morning and heard a sleepy voice behind tell her to get back into bed. She said later she had ‘physical needs’. Such is life.

So when the weekend that changed my life rolled around I was well and truly single, and perhaps a little too strung out for good judgement – though it would be more accurate to say I was emotionally starved of female company than I was in need of dropping a physical load. I had the internet, right? In body I could do it myself, but it would have been nice to be with a real woman for once, not imaginary.

At the time the weather was glorious but Jimmy had a rotten summer flu. He was sick in bed, there was no chance he was going to come out of his room. I’d seen him like this before, he was the type rip her up porno to crawl into bed and sleep the sickness off. Even if he needed the bathroom he had his own en-suite in there.

On Friday night Sara had come over straight from work to look after him. Her white shirt and formal skirt were more conservative than normal, but still she looked smoking hot.

After trying her best to play nurse Sara decided to sleep on the sofa to avoid catching Jimmy’s flu. She dragged out a spare quilt and came into the living room. I was watching Chef on cable on-demand. I filled her in on the back story of the first 20 minutes, it’s not a complicated film.

“Can I sleep here tonight?” she asked, though we both knew it was more her place than mine, she was the one sleeping with the owner.

“Take one of the spare rooms, it would be more comfortable,” I suggested politely.

“Nah. I like it here.”

I was on the carpet leaning on one of the single sofas as Sara settled in. After a time she started to do stretches and bend-overs sitting on the long sofa. It looked in the light of the TV that she was grimacing.

“Are you okay?”

“My back hurts. I’m not sure if it’s just my back or the start of Jimmy’s flu.”

“Can I help? Get some medicine?”

“No. No, don’t worry.”

A little while later though she said, “Actually yes”. She asked me to come over to her sofa and turn around. “Sit here.”

She lightly ran her hand up and down my spine.

“Just rub my back like that. Don’t do it hard, guys always push too hard. Just lightly like that. Got it?”

“Yeah”, I said, a bit excited. As innocent as it was, laying hands on Sara in any capacity was boner-inducing.

She crawled down and lay face down on the soft clean carpet, her head on her arms folded in front. She closed her eyes. I completely forgot the movie. My only interest in it was the flickering light it gave, showing me the glory of what I was doing with that beautiful woman. That and the funky salsa music.

I ran my hand lightly up and down her spine on the outside of her soft light-blue pyjamas.

“Like that?”

“Yes,” she quietly purred. I did it some more, being careful to keep her pyjama top flat and not get caught on the bump of her bra strap. I felt excited yet terrified. What if Jimmy knew I had hands on his woman? I couldn’t imagine it would go well, he had a wild temper. Unexpectedly Sara unfolded her hands to reach behind and lift her top up her back until it was bunched under her arms and around her neck. She flicked the clasp on her bra before folding her arms up again and laying her head back on them.

Holy shit.

I was painfully hard. Sara had just given me her naked back to feel up. I tried as hard as I could to massage her the way she wanted, lightly and up and down the middle, but it was difficult to keep restraint. I couldn’t help but run my hands around her waist, and over her shoulder blades, under her bunched-up pajamas to the nape of her neck. I squeezed with all the gentleness I could muster and Sara groaned that it felt wonderful.

I didn’t completely abandon her aching spine but my departures became wider and longer. I expected I would hit a boundary and be slapped into line but Sara aaahed and writhed at my touch which emboldened me.

I wanted to say ‘you feel nice’, but didn’t. I worried my voice would break the spell. Nice wasn’t the right word, anyway. Her body was spectacular; a tiny waist with elegant shoulders and a delicious curve to her back. She was sensually smooth.

“It feels nice,” she said and I almost laughed.

I ran my nails down her spine and swung around to her side. I really really wanted to run my hands along the side of her squashed breasts but dared not. Instead I skirted the hem of her pajama bottoms, testing her reaction to pushing the elastic down. Sara’s breathing was heavy, almost like she was asleep. She didn’t flinch at all to incursions into the borderlands of her pants.

I tried to make it as natural and accidental as I could, sweeping high up her neck then low on her back, my hand in and under the loose elastic. As each sweep made it further inside there could be no mistaking my intention. Sara must have realized what was going on. So I went for it, down into her bottoms looking for her panties.

I didn’t find any.

There was no underwear under her pajama bottoms. It wasn’t at all what I expected. I accidentally held all her bare ass in my hand. I moved away as quickly as I could without letting on how shocked I was. My heart was racing. If she told Jimmy I felt up the bare skin of her backside…a shiver of fear went down my spine.

“Don’t stop,” I heard her moan sleepily.

Oh, I thought. Was it really okay? Could I actually do what I just did, again? Or was she setting me up for a beating, for her own twisted pleasure? I instinctively looked at the door to check, even though there was little chance Jimmy could be up.

Taking rus porno a big chance, I went back into her pants, stretching them. I did my best to stay gentle as I ran my hands over her small shapely rear and the top of her thighs, still pretending to massage. I made the occasional run along her back and shoulders but I just couldn’t stay away from her bottom half for long. It was unbelievable that I was even there with Sara, let alone with hands on her like that.

I ran my fingers lightly down onto the inside of her thigh. I could sense how deliciously close I was to her heat. I went up and down her inside leg, getting higher each time. Without any push-back, I was getting bolder and bolder. I was fondling her ass, not massaging it anymore. I ran my finger down between her legs. I could feel her folds, I had reached her pussy. I felt a hint of wetness, my head spinning.

Sudden movement shocked me away from there. Sara’s whole front half lifted, I moved my hand out of her pants and braced for the worst. Surely she was about to rip my head off?

I was stunned to see her lift the blue pajama top off and over her head, and the bra straps down her arms, laying back in the same way as before completely topless. For longer than was cool, I froze. Surely this had to be a sign of permission? I took a big chance; to be wrong may be deadly, but to be right would be heavenly. I pulled at the hem of her bottoms, pulling them down over her ass. Sara lifted her hips to make it easier to drag them away. I went over her knees and her ankles, and off. Wow. I was fully dressed (in sleeping kit) and Jimmy’s stunning girlfriend was stark naked face down on our living room floor. In the light of the TV she was everything a woman should be; shapely, clean, sexy. Her perfect naked curves and the sheer beauty of her face in profile reminded me of those artistic porn photos you see, usually in black and white, laying in half-light. Was I actually asleep in front of my computer, dreaming?

I pinched myself. Ouch. It was real.

For the longest time I drank her beauty with my eyes before I dared reach out with my hands, lightly touching everywhere, from her ankles to massaging her head through her hair. But it was all a tease for myself, I had my heart set fiercely on the darkness between those perfect thighs. I couldn’t help it. All my touch was circling toward there. When I again ran my finger at the very top of her inside thighs, they parted ever so slightly.

I gasped when I felt her pussy properly. Not just because it was leaking wet, or that it was hot and soft. What shocked me to the touch was Sara was completely and utterly bare. I had no idea. I hadn’t even dreamed such a thing. I cupped her mound. She had completely shaved her pussy, as smooth as the rest of her. I almost came in my pants, fighting to hold my sperm inside.

I dipped a finger inside her. There was little resistance. Sara’s arms stretched out in front of her and she groaned. I twisted and flicked her insides and she gripped the carpet and shook. I put a second and third finger in and wiggled, searching and learning the shape and size of her insides. It was tight in there, but not so much that it was uncomfortable; she could stretch to fit me. After a period of consolidation I used those fingers to fuck her like I would with my cock. She lifted her hips to give better entry.

This time I would say it, “Sara you’ve got a great cunt.”

She turned back to look at me. A hand went to my thigh, then to my cock on the outside of my pants. I knew it was wrong but my hormones had taken over. Forgive me Jimmy, I thought, as I pulled them down and placed her hand onto my raw penis. I fingered her as she tugged me. I flipped her over to see that bare mound and tits for the first time with my own eyes.

“Oh, shit,” I couldn’t help but say. How could someone so beautiful, with such a dynamite ass and pussy, also have such splendid tits? It wasn’t fair to other girls. They weren’t big but they stood straight up even though she was on her back. I wanted to ask if they were natural, but didn’t.

There was no messing around. Sara shuffled over and positioned herself in front of me, on her back with her thighs open. It was an invitation, one that said ‘quick, before I change my mind’. She literally reached out for my cock and pulled it to her hole, rubbing me up and down herself to get wet, then pulling my hips to hers. Her mouth was open and her eyes pierced mine. She gasped as my cock pushed her open. Her head went back as I hit full depth. She reached up to scramble my top over my head so we were both naked.

“I like it naked,” she panted as I slid in and out.

She didn’t say how to have sex with her, but her eyes told me to do what I could.

What an experience. Apart from the sheer beauty and sexuality of the spectacular nude beneath me, it was completely and outrageously wrong. Sara was Jimmy’s steady. They’d been together for almost two years. I’d known them all of sert porno that time. The fact that this was the first time I’d seen those breasts or had any idea she was shaved is a true indication of the intimacy we’d shared over those two years – absolutely none. Yet there I was with my bare cock in her bare pussy, fucking like high school kids on the living room floor.

I wanted to talk. I wanted to say how amazed I was to be inside someone so beautiful. I wanted to ask if she was sure she wanted to do this? Wouldn’t she feel guilty later? How could we face Jimmy after doing this? But I said nothing. I leaned down to latch my mouth on those stunning breasts. How could they be so tight? I could feel her cunt slide and slop and fill with air as I pumped it. Her nails dug into my ass. We flipped and she rode me, her hips as enthusiastic as any girl I’d known. Who knew Sara would respond so amazingly to cock? It was a huge surprise.

She pressed her tits to my chest and kissed like she was pashing me, pushing into my jaw and invading with her tongue. I held her ass, in rhythm with her grinding. Was it me that excited her, or did she masturbate herself to that orgasm? I’ve never had a girl do that, not a real one. And Sara, she squirted. Her hips shuddered on my cock like an electric shock was zapping through them. Her lips went to my ear.

“Cum. Please. Cum.”

How could I not? I didn’t even ask if she was on the pill, I just lost it. Rope after rope of semen splattered Sara’s insides.

“Oh god,” she said kissing my lips hard. Her cum kept on past mine. Finally we came to rest with her body on mine, out of breath. My half-hard cock was still in her, sperm and air gurgling. I held her fabulous ass tightly.

“That was…that felt good,” she said kissing my face with delicate small pecks. “I’ve always wondered what it would be like with you. Thank you.”

“Your back feels better?” I teased.

She laughed and lifted herself. As my cock dropped out, a trail of semen poured from her bare flaps. She knelt over me with her hand between her legs holding it in.

“That was a big cum,” she said.

“You or me?”

“You! I could feel it. How much did you put in me? A whole carton?”

“You’ve got brilliant tits,” I said, changing topic. “Can I have them.”

I dragged her down and put one in my mouth. Sara held herself over me, taking her wet hand from her pussy and rubbing in on the carpet. Silently she watched as I tattooed her breast with a hickey, right above the nipple. Looking at how huge it was afterward I wanted to ask what Jimmy would say, but held off.

“Can I have my actual massage now?” was all she asked.

I laughed. “Sure.”

Sara lay in the original position and I massaged her all over with my hands and lips, long enough for me to get hard again. She giggled at my prowess as I pushed into her pussy again, from behind this time. Having cum already, that second fuck was a long, slamming affair. Physically we connected well, I seemed to be able to sense when she needed more of something, or was ready for a change of position. We turned and twisted, we sat on the sofa in all sorts of contortions and even lay her on the coffee table as I knelt between her thighs – though not for long, it was cold on her back. It was remarkable she could stay wet and fuck so enthusiastically for that long.

“Last weekend I was away, and the weekend before was my period. I haven’t had it for 3 weeks,” was her explanation. “3 weeks is long time…for me anyway.”

I was dreading her asking me when my last one was. The answer would be embarrassing. Luckily she didn’t.

In the end I couldn’t help it, I fell asleep laying behind that beautiful woman on the carpet, one hand around on a breast, my softening cock falling out of her pussy along with more of my semen. I was blissfully tired.


I woke in half light, sore from having slept on the floor. I was covered by Jimmy’s spare quilt that Sara had brought down.

Sara. Where was she?

I turned to see her squatted next to me putting on her bra. The light was low but she looked naked otherwise.

“Where are you going?” I asked

“Shhh, sleep. I’m not meant to be out here naked with you, remember? I’m going back into Jimmy’s room.”

“It’s still early. Stay a bit longer. Please.” I reached out to touch her thigh. Sara hesitated. I took the opportunity to shuffle closer and push my hand to the top of her inside leg. I pushed sideways, asking her to open for me. Sara sighed and opened one leg, giving me her clitoris.

“I may not have this again,” I said.

“You can’t,” she whispered

“So don’t go yet. Just a few minutes more. It’s still not proper light.” I shuffled next to Sara as she sat with her legs under her, my finger creeping down, drawing wetness from her slit. I pulled the quilt off me, showing the outline of my morning wood.

Sara reached out and held it, slowly tugging in sync with my two-finger forays into her vagina.

“We can’t do this,” she moaned. “Jimmy would kill us both.”

“It’s still early. And we already did it. Just a little bit longer…”

Sara was squeezing my cock hard, perhaps surprised I was so ready for her.

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