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First Time with Tom

By: seteais



My buddy Tom and I were sitting in my kitchen drinking beer when the topic of conversation, which up to then had been about the chances of the city's football team ever winning another game, turned to sex.

Tom and I were getting to know each other again. We had run into each other several weeks before at our high school reunion. 

I recognized him immediately. He hadn't changed much in twenty years, although he had packed a few pounds on his swimmer's body. We hadn't been close in school, so I was surprised that we seemed to hit it off so well. So well that now we were hanging out two or three nights a week.

It was Tom who brought up sex."I bet you didn't know we're Eskimo brothers," he said, as a wide grin spread across his lips and lit up his eyes.

My baffled look answered the question. He chuckled and finished his beer.

"You didn't know?" he said. "You remember Pattie Sue?"

"Yeah." I said. She had been my first.

"I fucked her." He leered at me. "I think you did, too."

"I did," I admitted.

"There you go!" he said. "Eskimo brother!"

"I think she fucked everybody in the senior class," I said. "Did you see her at the reunion?"

"No. I looked for her. She didn't come."

"Didn't come for me either, as I recall, I said."

"Maybe you weren't big enough," he said with a smirk. "She came when I did her."

Tom was hung. I remembered eying his big cock in the showers after gym class. I envied him.

He spent the next twenty minutes and two beers going on about all the girls he had nailed in high school. Tom tells great stories; I pictured the girls he said sucked and fucked his big cock and began day-dreaming. He interrupted my fantasy with a question.

"How about you? You getting any?"

"Oh. Not since Emily left," I said. 

"What was she like?" he said. "I mean in bed."

"Okay." I didn't want to talk about Emily. It only reminded me how much I missed her.

"Come on, 'okay' is all you can say about your girlfriend?"

"Ex-girlfriend," I said.

"Yeah, yeah. Okay. Did she blow you?"

"Yes, she blew me, and I went down on her," I said with an edge of anger.

"Hot. Was she good?"

"Like I said, she was okay."

"On a scale of one-to-ten, how would you rate her?"

"Jeez! You're obsessed with blowjobs." Actually, it was me that was becoming bewitched about blowjobs. I couldn't stop thinking about, his big cock.

"Come on, rat her. I mean rate her"

"One to ten? I'd give her a four." I said, "I could do better."

"What do you mean 'do better'? You ever suck a cock?" 

"No," I lied, I had actually sucked two. "But I think I could give a better blowjob than Emily."

"Prove it," he said, getting to his feet.

I was suddenly as nervous as a preacher in a titty bar. What was I doing?

Before I could back out, Tom unbuckled his belt, unzipped, and dropped his jeans. He wasn't wearing underwear and his cock popped out like a quick draw and straight as a gun barrel pointing at my face. My eyes widened and my mouth went blotter dry. 

"Put your money where your mouth is, I mean your mouth right here," he said. He smiled and began stroking it. "Come on, don't lie. You've been thinking about it all night."

My heart thudded. He must have read my mind. I reached out and grasped the biggest cock I had ever seen. I felt the girth as I wrapped my fingers around it and got even more aroused. I slowly stroked it, sliding the tight skin back and forth. Pleasure showed in his eyes. His cock felt hard as a hammer handle and almost as long. He was breathing in short rasps. 

I couldn't resist the urge to take his cock in my mouth. I slipped off my chair and dropped to my knees. I looked up at him, the unasked question showing on my face.

"If you want to suck it," he said, almost a whisper, "I don't mind."

Close up his cock looked enormous. I took the head in my mouth and squeezed it with my lips. I rubbed it with my tongue. I fondled his balls. Tom gasped and moved his hips. 

I ran my tongue around the head of his cock and up and down the shaft. I took about half the length in my mouth and sucked. He moved his hips and I let him fuck my mouth. My hands shook as I grasped his strong thighs with both hands. I was getting hard.

All at once Tom thrust eagerly. His body tensed and his cock swelled in my mouth. Shots of cum burst out of it and gagged and choked me sliding down my throat.

He looked down at me. The corners of his mouth turned up and his eyes crinkled. "You all right?" he said, suppressing a giggle. He wiped a gob of cum off my chin with his finger.

"I wasn't ready for that," I said breathlessly.

"I got off quick. It wasn't much of a blow job, but it was fucking exciting. That's why I came so quick." He pulled up his jeans and buckled them.

I climbed back on my chair. "I just swallowed a shit load of your cum and you say 'It wasn't much of a blow job'?"

"Oh, I'm sorry, did I hurt your feelings?"

"You did. I thought I did pretty good," I said.

He frowned at me and patted my head. "Sorry. Would you feel better if I said you're a great cocksucker?"

I mumbled "Uh-huh. Only next time let me know when you're gonna come." I hoped next time he wouldn't get off so fast so I could suck that massive dick longer.

I didn't think next time would be so soon. 

Tom said, "Let's go in the bedroom. That took the pressure off, now I'm ready to get down."

I couldn't refuse. I was aroused as a gerbil in heat. I led the way to the bedroom.

We tore off our clothes and I grabbed his cock, only half-hard now. I sat on the edge of my bed and began sucking him again. He got hard quickly and I wanted that huge beast in me.

"I want you to fuck me," I said, croaking out the words. 

"I thought you'd never ask," he said. I fumbled in the drawer of the night stand and brought out a tube of lubricating jelly. The plastic tube made a farting sound as I squeezed some lube out into my shaking hand. I smeared it on his cock, stroking it and circling it around the big head. I wiped my asshole with the lube and probed it with two fingers to wet and loosen it. I knelt on the bed and Tom climbed up behind me. He began to slither his cock up and down the crack of my ass.

"I'm going in, easy," he said. "Okay?"

"Yes." I wanted his cock in me, wanted to be filled with it.

He put a finger in my ass gently, and moved it in and out. "Try to relax."

Tom removed his finger and replaced it with his cock. He was pressing it into me. It felt hard and thick as a baseball bat. I had a moment of dread, but I couldn't chicken out, so I just said, "Okay, okay."

He pushed a little harder. "Going easy. You okay?"

"Uh-huh. You can push a little more." I didn't say it, but I wanted him to slam it into me and split my ass in two.

I focused on relaxing my ass and he put the head of his cock in a little more. I grunted.

"Still okay?" he said.

I nodded and another inch came in. He pulled back and pushed again. Another inch. It was beginning to hurt. I felt a burning sensation as he pushed again.

"God, you're tight," he sighed.

"I think we need more lube," I said.

He withdrew. I grabbed the tube of lube and squeezed a glob as big as a quarter into my palm. I reached back and slathered lube on him. His cock was as hard as a doorknob. I rubbed the rest on myself and pushed two fingers in as deep as I could. "Try now," I told him, and put my head on the pillow and reached back with both hands and spread my ass.

"Going in," Tom said, real easy."

I felt the pressure of his cock, cold with the lube, and willed my ass to relax, to just let go. Suddenly he put more force behind it and I felt his cock slipping little by little inside me. I clenched involuntarily and when I let go I felt it moving in and out as Tom started thrusting. In and out, each stroke probing a little deeper into me. It felt incredibly nice. I began to moan.

"I'm getting there," he said. "Is it okay?"

"Hell, yes," I groaned, a bit too loud.

Tom pulled out. I felt empty. He grabbed my hips and rolled me over. He got off the bed and dragged my legs over the side and my feet hit the carpet. Then he spread my legs and put his cock back where I wanted it.

"It's good, man, it's very good," he said, sounding out of breath. He had my shoulders pinned to the bed and he was ramming me roughly. 

I felt totally submissive, fully under his control. His cock slamming in and out of my ass was unbelievably good. Every thrust sent waves of pleasure through me. I knew then if it got too intense I couldn't stop it. Excitement seemed to fill the room and I submitted to it. I was in a state of ecstasy I never felt before, didn't think possible.

"Yes," I groaned, out of my head. "Fuck me, fuck me."

As he pumped harder and harder, my ass went slack and he buried his mammoth cock in me. He was breathing hard. Our balls were touching. My fully erect cock was bouncing against my groin. I moved my hips to match his thrusts. 

I don't know how long we fucked. It seemed to go on and on. More strange and wonderful sensations never felt before swept through me, setting me on fire with pleasure.

He continued to thrust deep in and out and suddenly I stiffened and was wrenched with a long, intense anal orgasm. It was like coming, only deeper. The spasm squeezed his cock so tight he moaned.

My ass was loose as an old whore's pussy and he pounded faster and I felt the beginning of an orgasm. Tom moaned. I felt his cock grow bigger and harder. My balls squeezed tight and my cock stiffened. I felt spurts of his hot cum deep inside. Spasms of ecstasy began, gentle at first, then, each one more intense, until an explosion of pure pleasure drove me so totally mindless I can't even describe it. I sagged down on the bed and felt the puddle of my cum on the sheet hot against my chest.

Tom helped me back on the bed and flopped down next to me. "Oh, fuck!" he croaked. "That was fan-fucking-tastic!"

I agreed but I was too wiped out to speak. I nodded my head on the pillow. I reached over and squeezed his cock. It was soft and hot and sticky. Cum seeped out of my ass.

I must have dozed off for an instant before Tom slapped my ass and roused me.

"Hey, you're my bitch now," he said, chuckling. "I made you my bitch."

"Yeah, I'm definitely your bitch," I said groggily.

He slapped my ass again. "I love your bitch ass," he said.

"I love your cock in my bitch ass."

He rubbed my ass cheeks. "This is a great ass."

"Are you going to admire it or put something in it?"

"Really? You want some more?"

I spread my legs wide and wiggled my ass. "If you have any more, I'll take it."

"You got it, bitch." He grabbed a pillow and shoved it under my pelvis. He climbed between my legs and eased his cock deep in my upturned ass. I groaned. I'd be sore tomorrow but I didn't care.

"Oh, fuck me," I moaned.

Tom leaned on his hands and thrust. I sobbed with pleasure. I was his bitch, and I hoped I'd be his bitch for a long time.

First Time with Tracy and Mike



This story gives me mixed feelings. I've just ended an eleven-year wife sharing relationship with a couple of dear friends. But I have fond memories of them, and what we did together inspires me to try and meet someone new. 

Mike and Tracy were neighbors. They've known my wife, Teresa, since grade school, while I've only known the three of them since college. 

They grew up together in a close-knit Italian-American neighborhood. Tracy and Teresa are actually both named Teresa; but Tracy's mother gave her the nickname from an early age to avoid confusion. I'm of Swedish-Danish descent and was raised in New England, not far from Boston. 

Mike and I began to chum around in college when our then-girlfriends used to get together. They were inseparable, and fortunately Mike and I hit it off too. We like to watch sports together, mountain bike, hit the bars, what have you. 

When we graduated college and started working, it was the most natural thing in the world for us to buy homes in the same neighborhood. Mike and Tracy lived a couple blocks away, on the other side of the street. When the babies started coming, our kids played together too. (They had two sons and a daughter, we had two daughters.)

My marriage was always happy and fulfilling, except for one thing: Teresa hates sex. I attribute it to both her mother and grandmother telling her it's a wretched, dirty, degrading thing that every woman must endure for her husband. While she is every bit capable of forming her own opinion, the early input she received from the women in her family nevertheless had a big impact on her. 

She seldom had sex when she was dating. Even on our wedding night, she accepted my cock with a turning away of the face and a stiffening of the body. 

After I would come, she would rush immediately away to clean up. 

The only time she ever came with me was when she was drunk. I was going down on her, lovingly licking her beautiful little clit, and slipped a finger into her quivering pink. Her tight little pussy squeezed down on my gently probing finger, and she let out a little cry, just "Ooh!" That was it. We fucked next, but as usual she was just going through the motions, for me. However, I caught her digging it, and hoped she might come again, but it didn't happen. I came hard into her, turned on by her reaction to being eaten, but she then took right off after to go clean up.

This was our sex life- me mostly going without because I love her, and her occasionally "submitting" to it because she loves me. We did try therapy, counseling- to no avail. The conclusion? She hates sex. If it was due to a treatable issue, thousands of dollars of therapy failed to find it.

My relationship with Mike and Tracy began eleven years ago. The kids were now in grade school, and we used to cook out and have pool parties at one another's houses all the time. Other people would be there at various times, but it was always our two families at the center of it. 

It had been a big blowout- we'd had about thirty people at my home for a barbecue. It was night, and most of our guests had left. Tracy's sister and brother had taken their kids for the rest of the weekend. 

We went inside to the den, and were shooting pool. Except for Teresa, all of us were pretty liquored-up, and no one was feeling any pain. When it came time for the kids to go to bed, I kissed them goodnight and Teresa said she'd see them off to bed. She also said she guessed she was pretty beat, and decided to turn in early. 

We continued to drink and play pool, and I kept ogling Tracy. Though both she and my wife are Italian, Teresa doesn't look it. She's Tyrolean, and has blond hair, blue eyes, and is petite. Tracy and Mike are of Tuscan descent, with olive skin and very dark eyes. Tracy is tall, curvy, and has a beautiful head of long black, wavy hair. 

Tracy was wearing a bikini with just a pair of flip-flops and a man's button-down shirt for "modesty's sake". (We were nothing, if not casual). Mike and I both had on swim shorts and button down shirts. Tracy kept bending down to take her shots, and I couldn't take my eyes off her chest. She has big breasts, at least 38-D's, and her nipples were protruding very invitingly through the fabric of her bikini top. She caught me looking, and gave me a sly smile. I began to feel very warm. 

We were playing our last round, and Mike jokingly asked what the prize would be for the winner. 

Tracy looked right at him, and said, "Well, you know what you could give ME for a prize, Honey!"

He blushed almost purple, and said, "Come ON, babe.... let's not air this out in front of Dean...."

I knew what they both meant. Tracy wanted oral sex, had enjoyed it from her teens, and Mike just doesn't care to provide it. He'd told me many times that he liked to please her, liked her natural scent, but the taste just repelled him. He'd tried every body sauce and flavored massage oil in the world, and it just didn't work. So Tracy's pussy went pretty much unlicked, although it was fairly common knowledge that he knew how to make her feel good otherwise. 

"Honey, PLEASE take care of me," she was nearly begging now, "tomorrow's my BIRTHDAY. Make me a happy birthday girl!"

Mike just scowled, mumbled a bit, and spoke up and said, "I think I'm about through playing now." He was so embarrassed he could hardly speak. 

Tracy, however, was quite loaded and wasn't going to be denied so easily. 

"What about you, Dean? I bet YOU like to use your mouth on a girl!"

Mike sputtered, "What the FUCK, Tracy! What's wrong with you??"

She kept on. She leaned on me, and whispered boozily, "Deannn, you're SUCH a good friend.... just give me a SPECIAL little birthday kiss...." then, she giggled. 

Now I was embarrassed, too. I met Mike's eyes and shrugged. He shrugged, too. Then, unbelievably, he asked, "I don't know... what do you say, Dean? For her birthday?"

He blurted on, "Come on man, I know you want to make her. Nothing wrong with it, EVERYONE wants to. So, you want to take care of her?" Tracy, who had been staring owlishly at us, chimed in, "Oh PLEASE Dean, no one but us would have to know!"

It must have been the beer talking, because I heard my voice saying, "I'd love it. Lead on!"

My face was blazing crimson, but at the same time I began to feel a stirring in my dick. 

We walked down the block to Mike and Tracy's house, and she led me up to the bedroom. 

Now we stood around in a nervous little knot, unsure how to proceed. Mike said, "I don't know, Dean... You want to be alone with her? I mean, I know that's normal, but I feel weird just leaving her with you..."

"NEVER mind Mike," Tracy replied, "you come along too. Why don't you watch us?" It felt weird to me, but I wasn't going to miss the opportunity of a lifetime. 

I sat on the bed, and Tracy climbed into my lap. My erection sprang to full life, tenting the front of my shorts. Mike retreated to the back corner of the bedroom, watching quietly. Tracy touched the end of my still-clothed hard-on delicately, and whispered, "Nice!"

We began to neck like two school kids at a drive-in. I kissed her deeply, tasting her lips, probing her mouth with my tongue. She met my tongue with hers, first cautiously, then with abandon. We both began to breathe hard. I peeled the shirt off her first, and ran my hands over her big, beautiful body, pausing to cup my hands under her big cheeks. She gave a little quiver, and reached up to unsnap her bikini top. 

Her boobs were gorgeous. They bounced free, high and proud, nipples erect and a delicious dark cherry color. They were so gorgeous, I was almost afraid to touch them. I tentatively placed my hands on them, cupping them carefully, caressing the silky skin gently, feeling their weight and firmness. I lowered my head to her chest and began to lick and suck her nipples. 

"Oh my GAWD, that's nice!" she breathed, as I kissed around each nipple in a circle, swirled my tongue around them, blew on them, then sucked them softly with my hot lips and tongue. Her hand stole gently down the front of my swimsuit, and her soft hand encircled my throbbing manhood. 

She lay back, and I eased my hands between her bikini bottom and her luscious round hips. I eased it down by her hips, over her big, inviting thighs, and off her with a soft whisper of fabric. 

She spread her long, muscular thighs and showed me a feast fit for a king. 

Her pussy was quite hairy, but the hair was neatly trimmed short. The labia were a delectable dark pink color, and were glistening with moisture. Inside her peeked an enticing glimpse of paler pink, soaking wet. Her pussy was not small, but it was one of the prettiest I'd ever seen. 

I kissed my way up her thighs, placed an affectionate kiss on her erect love button- a delighted shudder ran through her body! and kissed my way up to the cup of her navel, leaving her starving pussy to wait unattended for a moment. 

When I worked my way back down her belly to her pussy, a sheen of goosebumps covered her skin when I began to tongue her juicy labia, first the outer, then the inner. I savored the luscious scent of her aroused pussy, the slightly bitter taste of woman on my lips. I couldn't get enough of her pretty pussy. 

She moaned deep in her throat, and began to rock her hips slowly. I kissed all around her pussy, then began to lick upward on her erect clit with tiny, butterfly strokes. Next, I eased first a forefinger, then the middle finger too, inside her. It was hot as lava in her, and drenching wet. Sliding my fingers slowly back and forth, I timed my fingers and my tongue to the rocking of her hips. 

She moaned louder, and her motions became less graceful- almost staccato. Her breath hitched, and I held the rhythm of my tongue and fingers. It occurred to me she might take a while to get there because she was drunk, but it was not a problem!

"Oooh, ooh...", she sighed, then let out kind of an, "AH!" and jerked her hips strongly. Her powerful thighs clamped on my probing hand, and her pussy was tucked between them, out of reach as she sailed over the edge. Now she bucked her hips HARD, and at the top of each stroke, I gave her pulsing clit another lick. Shudders ran through her, and inside her pussy was a steamy swamp of love. 

She shuddered for a few more moments, then sat up as I eased my fingers from her. She looked at me with slightly fevered eyes as I licked her moisture from my fingers, then SEIZED my shirt and yanked me to her, covering my lips with bruising kisses. All I could hear from her was "Mmm, mmm, mmm..." as we kissed. Finally, we disengaged. She looked at me, panting. Then, we both looked to the back corner of the bedroom. We'd forgotten Mike. 

He'd shed his clothing, and had sprung an amazing erection. He had a big, thick cock, and was working it with firm strokes, using some hand cream from the dresser. His eyes were a little glazed, and he was hugely turned on by the sex show I'd just put on with his wife. 

Tracy saw this, and immediately said, "NO hon, don't waste it! Come to me...."

She scooted to the edge of the bed, then lay back, spreading her long, graceful thighs wide. Mike carelessly wiped his throbbing member on his shirt, getting rid of the hand cream, and tossed the shirt to the floor. He crossed the floor in seconds. 

He looked at me kind of sheepishly, cock throbbing and a big drop of come forming at the tip. "Dean... Sorry, man, I've just got to...."

I understood. "No, it's okay." I went to leave. 

Tracy looked up, and said, "Wait... wouldn't you rather stay?" She caught Mike's eye, and he said, "Yeah, man... please do! But, I can't wait any more!"

I took a spot a short distance from the bed, where I had a bird's eye view of the action. We were all kind of self-conscious for a moment, but they soon forgot I was watching. 

Mike took Tracy by her big, round hips, caressing them with long, sweeping motions of his hands, then slid them up and took her around the waist. Then, he grabbed his bobbing hard-on with one hand and slowly, carefully tucked the head between her juicy labes. 

They moaned together as he teased his throbbing head all around her wet slit. "OOOHH come on, fuck me!" Tracy hissed. Mike buried his throbbing pole into her inviting wetness with one long, smooth thrust. I was almost surprised that she was able to take him all so easily. He groaned, "Ahhhhhh," as he bottomed out inside her. 

Then, He began to fuck in and out of her juicy treat, not thrusting fast but very firmly. He did a sort of half-swirl with his hips at the bottom of each stroke, pressing their crotches together very closely. Tracy's nails first eased along his contracting ass muscles, then drew blood. I was startled, but he kept thrusting powerfully, not losing his rhythm. 

They were totally into each other, and I was seeing a side of them no one else ever saw. 

Mike couldn't last long, he'd very nearly jerked all the way off before Tracy stopped him. 

He began to groan softly, a sort of "Mmmm. MMMM!" sound, and she groaned back in turn. His thrusts became stiff and he snapped his hips forward each time. "Oh yeah, babe, it's coming..." he breathed. Tracy moaned again, "Oohh...ooh, ooh" and gripped his driving buttocks with her nails. SHe was coming again, for the second time in ten minutes! 

Mike sighed heavily, and took Tracy around the waist. "OhGAWD, babe..." He thrust in about half the length of his cock, then stopped thrusting. I could see his cock pulsing. 

"Yeah babe... come in me!" Tracy hissed softly through her clenched teeth. 

Thick come began to ooze around his shuddering dick and slip out of Tracy. Her labia were wet with it; and it began to slip down her ass and onto the bed. It looked like it would never stop. Finally, Mike pulled out. His member was coated with both a flood of semen and Tracy's copious vaginal dew. More semen slid heavily out her her. 

I had my cock in my hand, and was masturbating furiously, using hand cream from the same bottle Mike had been using. This was better than any sex show I'd ever seen. I'd have given anything to fuck Tracy right then! I just wanted to fire off my own load... just needed a minute....

Tracy spotted me. "Dean, wait," she piped up sweetly, "don't YOU waste it, either." 

I stopped dead, dumbfounded, and just gaped at her. Mike looked at her, too. 

"Well, hon, don't you think Dean deserves a nice thank you for the.... birthday gift?" she enquired teasingly. Mike looked a bit shocked, then got into it. "Yeah, Dean.... I mean, it's kind of obvious you want some... how about it?"

I was kind of shocked too, but I'm no fool. Opportunity knocks once....

"Hell Yeah, I want to!" I answered heartily. Tracy started to rise, to go clean up. 

"NO; don't!" I blurted out, "clean up, I mean. I want you just this way." She and Mike exchanged a look, as if to say, "What the fuck?", but she gamely lay back. 

I stepped between her big, tasty thighs and took in the sight. Tracy's just-eaten, just-fucked pussy was glistening and still flooded with Mike's big load. I had never had any interest in group sex before, but I wanted to fuck her more than anything now. Tracy took my embarrassingly average cock in her hand, and guided the raging hard head between her come-covered labes. 

I was afraid of being utterly unable to measure up to Mike, but nevertheless thrust slowly into her until her labes were spread around the base of my cock. I just held it deep in her, savoring. It was very hot and wet in there, and though she wasn't tight, it felt really great. I began to fuck her, and each thrust caused a little more come to slip from her flooded pussy. 

The whole thing was too much. I only lasted a minute or two, and began to feel the spark at the base of my cock that signals it's time to come. A warm glow seemed to surround my plunging cock as I fucked Tracy's well-used vagina. "Aw shit, Trace... I'm sorry," I stammered, and stopped fucking her, trying to regroup. 

"Not at all," she whispered. "keep fuckin'. Come in me, Dean. Come in my used pussy."

I resumed thrusting. "Aww fuck, I'm coming!" I gasped. "Yeahhhh", she whispered. My cock felt like it would explode from the sheer pleasure as I emptied myself into her. I took her by the waist as powerful shudders of pleasure ran through my body. Come began to slip out all around my cock and out her very used hole. My ass and knees shook from the pleasure of it, and she gently took my ass cheeks with her nails. She knew how to finish the job!

I pulled out of her, and between me and Mike, their bedspread was definitely ruined. No one cared, of course. We were at the bed in a little cluster now, embarrassed by our unbridled fetishes and not sure what to do. But eventually we figured it out! 

That was the first time we ever did anything sexually together, and it opened the door to eleven happy years of all kinds of sexual encounters. My sexual relationship with Tracy didn't end until they moved to Utah, last year. I miss my fun couple pretty badly.