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The Proposition

Category: Anal Sex
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“I’ve never done that before, will it hurt?” she asked, sleepy eyed. We hadn’t seen each other in over a month, we’d been kissing and had shed most of our clothes. The atmosphere was heavy with lust, it seemed like a good time to ask.

“I don’t know, beautiful, I’ve never done it either. If it does, we’ll stop,” I answered. I appraised her mood, then added, “It might just be fantastic.”

She stared distantly at the bookshelves lining the walls of the living room as she considered the sex act I had proposed. My erected cock attracted her scrutiny and a seductive smile touched her lips. She drained her zinfandel and slipped off her lilac silk undies. Bingo.

He had left a phone message at my apartment asking me to pick him up at the heliport when I got home from work. Over a bite to eat he’d told me happily that his idea had worked, the new platform was successfully online, and that he had two weeks off. There was more. He’d showed me a two thousand dollar check payable to Gregory Wright: moving expenses. He’d been offered a new position at the main office, a good one in engineering. He’d said he was going to sell his house, and asked me to quit my job, move to Houston and live with him. I’d accepted at once.

At last, an end to the long, lonely separations and bittersweet satellite phone calls (he called them sexsats). Soundbites of raising kids and dogs on a pleasant suburban street in Houston flickered briefly in my mind. But there was no indication from him on how he felt about that. He liked my body, obviously, and in his methodical way he was moving to secure access to it in the future. Was there anything else happening here? Well, there would be time to reflect later.

When we’d gotten to his house he’d fired up the gas logs and I’d poured some drinks. We’d toasted to our future, then he’d asked me very considerately for anal sex. It was the first time he had asked me for anything unusual, but I wasn’t surprised by it. He had hinted on several occasions about wanting to do more with my ass than just admire it, but I had nervously laughed it off. I knew the idea fascinated him when rear entry gradually became his favorite position for making love. So far, though, I had resisted anal because I was afraid it would be painful. I had an sudden inclination to be obstinate and refuse again, in the face of this obviously engineered ‘romantic’ situation. But perhaps it was time to change my mind. He wouldn’t hurt me intentionally, I was certain of that. I looked at his ripe dick, well proportioned, high and hard, and decided that his proposition stimulated me more than it frightened me. Besides, didn’t roommates share everything with each other?

“It’s your lucky day, Wright. My ass is up for grabs,” I teased. He laughed, threw a duvet over the big Queen Anne’s chair next to the fireplace, and sat down. I stood in front of him and turned away.

“Do you want to use a rubber?” he asked, quietly.

“I’m OK without it, if you are,” I said.

“Then up against the rod and spread ’em, baby.” he said, playfully. I showed myself to him unashamed, opening my buttcheeks with my palms. He rubbed his hands over my inner thighs and through my crack. Then he spread my legs outside of his, pulled me over him, put a generous drop of lubricant on his finger and touched my butthole. I shivered. He held his dick up for me and I used the armrests to lower myself onto it. I was very turned on and when the bulbous head began to penetrate me, the thought of what I was doing brought on a small orgasm. Warm liquid trickled down one thigh. I took a moment to recover, then tried again.

“Wait, sweetheart,” he said, then took his dick and slid it back and forth through my wet pussy lips.

She became exhilarated when my naked cock touched her sex, and she grabbed it with both hands and leaned forward to sink her pussy onto me. I pulled her back. She whimpered, her legs shaking. She seemed to be building to a climax already, or maybe just ending one. I repositioned her luscious backside over my cock, and she lowered herself onto me.

“I don’t know about this, you’re awfully big,” she said fearfully, pausing.

“It’ll be fine,” I assured her. I was hoping that if I got her quickly past the initial entry things would proceed smoothly from there. So I held her firmly around the waist with my cock touching her butthole, wanting to make sure that she didn’t get startled and stand up. I flexed the muscles in my dick to harden it, then I lifted my pelvis and my wet cockhead slid suddenly through the muscular resistance at her entrance.

She stiffened and sighed, “Fuck.”

“Are you all right?” I asked her.

“I’m OK. Go slow.” She shook her head and her short chestnut hair brushed my face. Her leg muscles trembled from the effort of holding herself halfway up, and with her asshole clenched around the head of my organ, it provided an interesting sensation, to say the least. I could smell the musky perfume wafting up from between her legs. Wow, this was just about all the foreplay that I could handle.

He pulled down firmly on my hips, and eased himself inside me. I was very tight and he could not enter easily. I could sense his urge to fuck me growing stronger now, and I knew he was resisting the desire to ram himself in. I didn’t think I could handle that. He sunk his shaft a little further and it was too much, too quickly.

“No! I can’t!” I cried out.

He stopped immediately and whispered to me encouragingly, “Don’t worry, babe, I won’t hurt you. We’ll go at your speed now. Tell me if you need to rest.”

“OK,” I agreed. I usually take his advice in sexual matters, he’s more experienced than I am. I relaxed a little, and I felt myself open around his hardness. His dick is not extremely long, I can cover his shaft with both hands, but it’s fairly wide and his cockhead is as big around as an egg. I am petite and quite narrow in the hips. I knew what we were doing was physically possible, some of my girlfriends told me they loved it, but I still had some reservations.

He spread some lube on the shaft of his dick, then sat completely still. I settled down on him slowly, a little at a time, testing for uncomfortable feelings. As I engulfed his body with mine, the increasing pressure in my bowels made me feel like I had to take a dump. I resisted what I guessed was an spurious impulse, given the circumstances. When most of his shaft had been worked into me I froze and gulped at another unfamiliar sensation. I was feeling some pressure at the expansion of my butthole, nothing serious, but I also felt something deeper inside that stirred a forgotten memory. My body thrilled to the kind of adrenaline rush I hadn’t felt since my first orgasm in elementary school.

“Still OK?” he asked, concerned.

“Uh-huh,” I affirmed. I realized suddenly that this wasn’t going to hurt at all, it was fun actually. He was getting what he wanted, and it was starting to feel pretty damn good to me too. A win-win situation. I became elated.

She hesitated and I thought she’d taken as much of me as she could. But somehow she knew to adjust the angle of her hips and then abruptly sat down fully into my lap.

“We did it,” she said brightly.

I smiled, “We sure did, honey. You’re amazing.” It was true. I don’t think I could have done that. I’ve had prostate exams and just a finger was lively enough for me.

This was a long held fantasy come true. Fantasies are a good thing when you’re 20 miles offshore in the Gulf of Mexico, surrounded by roughnecks for a month at a time. I admit that thinking about taking her in the ass had inspired quite a few ‘manual pressure reliefs’ this past year. Her little tush sported beautiful third order curves that jiggled pleasingly when she walked. I couldn’t look at her in a skirt anymore without wanting to lift it up and fuck her from behind, which I do regularly. Now I was really livin’ in the tall cotton.

Our future looked bright. Holly and I had met through mutual friends on a dinner-dance cruise over in Galveston. We had felt an instant attraction and we’d been seeing each other exclusively ever since. She was serious about her career and worked long hours, so my lengthy absences didn’t seem to overly upset her, as they had other women I’d known. We trusted each other so much that we’d both had HIV tests and had recently stopped using condoms. Yes, we were having a lot of fun together, but did she want a protracted relationship? I hoped so. She was smart, funny, pretty, socially graceful. I liked her a lot.

I ended my reverie and took in the view. Her feet were off the carpet now and dangling against my shins. Her thighs were on top of mine, her nicely rounded buttocks pressed tight and hot against my groin. All the tautness in her body was gone, she seemed happy and relaxed. She leaned forward experimentally, and her perky little breasts and delicate waist were so beautiful it hurt to look. My cock was steel pipe hard, shot straight up through her asscheeks, penetrating her deeply. Her channel held me tightly like a pair of strong, velvet-gloved hands. Shit, my hormones really kicked in now. My heartbeat speeded up and hot blood flushed into my cock as I had a sudden mental picture of what this beautiful young woman and I were doing with each others bodies. She must have felt me growing into her and I swear she mewed like a cat.

He put a finger on my clit. I knew he meant well, but I didn’t want to come like that so I took his hands and cupped them over my tits.

“On my boobs, if you don’t mind,” I said. He pulled me back to rest against him. I could feel his organ enlarging inside me and my butthole was expanding quite a bit around its base. This was getting pretty intense.

He breathed into my hair, “Baby, you’re beautiful.”

I whispered back, “I feel your dick in my throat.” He chuckled and ticked my nipples. I jumped.

“You bastard,” I said, completing our little ritual. He squeezed his pubic muscles and moved his dick sensuously inside my ass. His mouth began devouring the back of my neck, I trembled as his tongue wetly tasted me. His strong hands rhythmically squeezed my breasts, sending gusts of pleasure through my body. God, this was much better than I thought it would be.

I cursed in a husky voice and said, “You feel wonderful.”

She put her hands on the chair arms and lifted herself up, but we were a little dry and my expanded organ now locked us together quite tightly. Her upward movement painfully stretched the skin of my cock over its hard inner core, like a condom. I tensed, and she sensed my discomfort and nestled her buttocks back down into my lap. Her weight was fully on me, and it was obvious that we were not going to be moving much, so we just rested there for a few moments. What do I do now? This wasn’t at all what I had pictured anal intercourse to be. I had imagined her on all fours, me kneeling behind deep stroking into her. Or possibly…

“Put your legs together,” I ordered. His breathing rate was slowing, and I sensed that the lack of movement would not be stimulating enough to get him off. This was unacceptable, but I thought I had a solution. I reached down to gently lift his ball sack and allow him to bring his legs together. Then I brought mine together on top of his, trapping his testicles comfortably in the hollow space between his legs and my bottom.

“That’s friendlier,” I said, satisfied. I knew that his balls were very sensitive, I could make him come by just holding his shaft and playing with them. I moved my backside around on his crotch and felt his dick jump inside me. It was working. Now I was really getting excited, I hadn’t touched myself but I was close to coming. I thought he might be too. Some sex talk, then, he liked that.

She reached under my thighs to get some leverage, and squirmed her ass around on my nuts. That felt interesting. How did she know these things?

“I’m really stoked,” she said suddenly, and pulled herself down, hard. My cock inched in a little further.

“What?” I said stupidly, taken by surprise.

“I want you to come inside my ass,” she explained, completely unembarrassed.

“Why you saucy little tart,” I chided. She rocked from side to side and spread her butt cheeks apart one at a time with her fingers, molding herself more tightly onto my genitals. I was balls to the wall, now. The heat where our bodies coupled was incredible.

She added quickly, “I’m ready, let’s go.” She rotated her bottom on me and bounced a little, really getting into it. We both groaned. I put my face in her hair and my hands on her waist and hung on for the ride.

Suddenly she stopped moving and turned her head back, her voice like heavy cream, “Mmmmm, come inside me, baby, I wanna feel you spurt. I’m gonna come all over your beautiful cock when you do. Everything’s OK, just relax and let go. It’ll feel so good, babe, you know it will. It’ll feel so good, so good.” Fuck! I was speechless. This was most fantastic sex I had ever experienced. I was so deeply inside this girl I could feel her pulse. Pre-orgasmic contractions were chasing through my cock, now. I tried to calm myself so I could enjoy this a little longer, but I was being galvanized by her words and the sensations her body was giving me.

As I wiggled my ass on him, a past experience came to mind, and I closed my eyes to visualize a handjob we had once shared. I love this as much as he does because he shoots more sperm than anyone I have ever been with. I had straddled his hips and stroked him off with baby oil while holding his organ straight up. He came hard, it was fascinating to watch the fleshy head inflate to the bursting point with each squirt. His dick had swelled and jerked powerfully in my grip and I had to hold on strongly to keep it upright. He’d shot long jets of come at least 5 inches into the air. It flowed down over both of my hands, hot and slick. The thought of him coming like that inside my rear end prompted a shiver of excited anticipation. It was going to be incredible.

She was a wildcat again, moaning and wriggling in my lap, actually waving her arms like she was dancing the dang twist or something. And every bounce was kneading and squeezing my balls indescribably. The sounds of our lovemaking, the scents of our bodies, the fleshy voluptuous feel of her, it was too much.

“Oh God, babe, here I go,” I groaned. I closed my eyes as I lost control, and felt the muscles in my sex organs tensing tighter and tighter until they spasmed. I heard her say something and felt her grab my balls. I hung on the edge, motionless. The quivering continued for a moment, then the muscles fatigued, became still, and released with a convulsive series of closely spaced, powerful contractions.

I sat bolt upright and stopped moving when I heard his warning, I wanted to feel everything. I said, “I love you,” reached between my legs, took his nuts in both hands and squeezed. He groaned and began ejaculating hotly into me, his hardness surging upward. As he discharged I felt a very pleasurable, luxurious warmth spreading higher and higher into my abdomen. Contractions in my pussy synchronized with his injections, and my anus clenched excitingly on his shaft. I felt a tingling in my whole body like I had struck my funny bone all over. This was heavenly.

I growled deep in my chest as I erupted into her, pumping gush after gush of hot sperm forcefully into her tight little ass, the orgasmic pleasure of the rippling emission up through my swelling shaft unbearable, pulsing cockhead wide open with paralyzing sensitivity, heart racing, lungs heaving, muscles straining, pelvis shuddering, I poured myself out through my cock into her softness. My consciousness narrowed to breathing and fierce sexual pleasure, everything else unimportant. I came back to my senses feeling the tight walls of her rectum ballooning away from my cockhead as the pressure and volume of my injected semen increased. I heard her gasp each time I shot into her. Finally, my contractions slowed as I emptied, but the waves of spasmodic pleasure continued as her sphincter tightened rhythmically, milking my cock. I almost couldn’t handle this, it was overwhelming. Then she fell back onto my chest and climaxed.

I sat impaled on his orgasming cock and was shaken like an antelope in a lions grip. His hips bucked under my ass and air escaped from my lungs in grunts. We were like animals. His body had become a tool of primeval male instinct, uncontrollably pumping into me everything it could muster. I was bulging with his flesh and sperm, insatiably draining him, completely receptive. It was unbelievably, deliciously sexy. I released his balls with one hand and two strokes over my clit was all I needed. I plunged a finger into my pussy and arched my back strongly against him as I peaked, groaning in delight at the unbearable ecstasy flooding through me. Overwhelmed by profound sexual release, my whole body convulsed strongly over and over.

Her shivering orgasm was extremely passionate. Her spasms subsided and then started again, resulting in another moaning climax. It was awe inspiring. She looked angelic. At last she relaxed on me, totally spent. We rested a little, my shaft buried in her warmth as we caught our breath. I kissed her neck and tasted salt while I caressed her breasts, my cock still spasming occasionally.

I wanted to try fucking now that we were lubricated. I put my feet on the floor on both sides of him and my hands on his knees, and started moving my ass up and down over his shaft, a little farther each time, coating his cock with semen. Soon I was slowly stroking along his full length. His dick felt liquid and silky inside me. It was good, different, but good. He begged me to stop, explaining that he liked what I was doing but that post-orgasmic sensitivity made it too intense.

“Maybe I’m too hot for you, old man,” I wisecracked, and lifted myself off him to get some towels.

“I think I have better motion lotion at my place,” she called from the guest bathroom, “we’ll try that next time.” She walked toward me, her silhouette was breathtaking against the shifting firelight. “I wonder what they’ll say at the bank. Maybe I can get a transfer to…” She stopped when she saw my face.

“Holly, I have to ask you something.” I said.

“Yes?” she replied, expectantly.

“Were you afraid?” She was quiet a long time, gazing at the fire. I thought I had accidentally insulted her.

She looked back and whispered, “Yes.”

“That I would hurt you?”

“No,” she said.

Thank God for that, “What, then?” I asked.

She made a face, “That I would fart.” I laughed, and she tried to glare at me. I realized I’d made my decision. I stood up and took her hand.

“I love you, Mrs. Wright,” I said, looking into her eyes. Her smile started, wavered. I nodded. We stood there for a long time, grinning at each other like idiots.

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