The Hookup: Beginnings

Some of my stories are true, some have elements of truth, and some are pure fiction. This one falls into the true category and I haven't decided how much to admit yet.

I keep a couple of the hookup sites on my hidden web browser. The thoughts of hooking up ebb and flow and occasionally I use the mail feature to communicate to all the guys who send smiles, winks, and dick pics. I used it once to have my first experience (First) losing both my oral and anal virginity and later for a hookup that fits into the elements of truth category. Some of it has been changed to protect the guilty.

It had been a while. Almost six years since I last had sex with a man. I still remember the smell of cock, the tug of flesh and the burn, ache, pain, pleasure of accepting the penetration and the little thrill of being taken. It had either been too hard to get away or the timing hadn't been right. But I kept looking out of habit. Wondering if the stars would align or even if I could still do it.

You get all sorts on gay hookup sites but most are about the moment. A fast and furtive emptying of balls and then anonymity. Bi guys like me on the downlow. The divorced guys. The players. Most looking for a fast hookup.

And I get a lot of attention. For one thing there were a lot of good pictures. A hobby of mine. And I wrote a pretty good profile too explaining what I wanted. And without getting too full of myself I have a good body and my face is never in a profile image. Lean and tall at 6-3, long muscular legs with a very round ass and very smooth ivory skin. One guy asked if I was of mixed race because of the skin but I am not. My cock is a very fat 2 inches and a quarter wide with elegant pink/brown skin and proportions. It's only six and half inches long but in my very biased estimation it looked good. Once in drunken teenage moment friends had seen it and proclaimed it a "horsecock" because they all had skinny inch and half wide cocks. The bottoms ignored my profile settings and I had lots of offers to suck it and more even though I had no interest. With men I was mostly a bottom are at least a versatile bottom.

Even with that attention it was difficult to get anything going. They'd want to do it right then or want me to host. Neither of which could easily happen but I'd engage just to see who was out there. The funny thing was that my first hookup was relatively fast and easy but there were all sorts of issues with reengaging. He wanted a boyfriend, tried to fuck me without a condom, and was pretty small. I could live with one but not all three.

Then there was the guy who couldn't host but wanted me to blow him at parks and the like. I was an oral beginner for one and it wasn't my primary thing. He was persistent but it didn't work out. There was one that stood out though but he was from down south. Richard from downstate. His message started out.

"I love your body. That beautiful ass I could worship. That thick cock I could suck. That soft skin I could stroke as I made love to your body." He was six hours away but I shared my private pictures anyway. It felt good to be so desired.

He reciprocated and what I saw made my mouth water even though I don't consider myself a connoisseur of dick. Thick, long, and veiny with an upcurve. It was oiled probably from jacking off and I looked at the pictures several times. He was too far away and honestly he looked way bigger than I had taken or could take. Especially now that I was out of practice for so long.

For whatever reason we kept talking over the year. The feeling of being that desired was heady. Way beyond the normal "want to fuck today? Can you host?" messages I got. He'd always say how much he liked my body and how he'd like to worship it. I'd send him select pictures too that weren't out there otherwise.

Then there was the message. "Going to be up your way on business in two weeks. Staying at the XYZ lodge in your town." I knew exactly where it was and it turned out to be one of my rare alone weekends where the wife and kids were going out of town. I had to stay in town to work.

I felt my mouth get dry and my pulse pounded. Was I willing to do it again? It had all been abstract with Robert the past year and here now it was suddenly a possibility. I looked at his profile again. That oily thick cock and I could imagine it in me. Could I get it in me? I paused before caution was pushed aside.

"I'm free that weekend and I'm ten minutes from your hotel" I typed and the response came immediately.

"Would you like to meet at 8 am at my hotel? I'll send you my room number when I check in."

I hesitated at the commitment. Was I going to go through with it. I could bail now but if I said I'd be there then I didn't want to be a flake.

"Yeah, I'd like that."

"Don't feel like you have to. I've been hoping to meet for months now to see if you're as delicious in person as you are in pictures. If you are then I'm going to want to ravage, worship, and make love to you. Is that something you want? I promise you'll never feel more desired."

I stopped. The blood in my head pounded with every heartbeat. It was a moment of truth. And I really wanted to feel desired as offered.

"I want it. 8 am Saturday."

"Great, I'll see you then. BTW, attached is my latest test. I haven't been with anyone in a year but if it helps put your mind at ease."

I sat back heart pounding and wondered what I had just gotten into. The test result were clear and I could see Robert's full name and address on there.

Friday afternoon I checked the site and Robert had messaged. "Room 402, south side. See you tomorrow."

My guts clenched but not in a bad way. I looked at the pictures of his cock again and could feel my mouth water. I was going to do it.

The next morning I was up at six and had coffee early to help clean out. The long unused enema kit hung full of warm water from the hangar on door handle as I threaded the lubed nozzle through my sphincter. The release of water made me shiver as I felt my bowels fill.

Expel, repeat until nothing but clear water and I shaved and showered. I stood looking in the mirror afterwards and then bent over. I was lightly furred with pale hairs but no zits. My anus was pink and tight and I lubed and fingered it briefly trying to imagine taking a cock into it again. A shred of doubt crept in at the tightness but Robert showed every sign of being experienced in the ways of breaking in holes for cocks.

Dressing was odd. I was dressing to seduce a man which is something I hadn't done before and the image of a giggly schoolgirl went through my head. He desired me and I wanted to be desired. The G-string was too flimsy. The jock seemed to much of a cliche. The regular boxer briefs said not really trying. White or black thong? White I decided. It was more virginal and I felt a little like a virgin at that point.

It cupped my package and the band rode up between my bare cheeks as I pulled the tight jeans on. Short sleeved open neck shirt and barefoot in deck shoes. I looked in the mirror and tried to decide whether I looked like a guy on his way to get fucked.

I was early and puttered around unsuccessfully. I could feel the strap rubbing my anus and I was highly distracted. Time to go. I grabbed a small go bag that had lube, condoms and wet wipes and drove over with my stomach doing flip-flops.

It was a suites style hotel and these rooms were the executive versions. 402 was on the top floor and was easy to find. I stood there a second before knocking and the door was opened almost immediately.

"Steven, so glad to finally meet you. Come in, come in. As you can see I'm not dressed yet." I stepped inside and took everything in.

Robert stood there barefoot in a white hotel robe. He was older but rugged with a trimmed beard and hairy chest. Tall, maybe bigger than me with heavy gray in both his hair and his beard but a visible vigor in movements.

"Not having a face picture online doesn't do you justice. How old did you say you were? 50? You can easily pass for 10 years younger." He stepped forward and stroked the side of my cheek.

"Very sexy. I more than stand by what I said. I want you. Badly." The robe came open and with it the first sight of his genitals. I must have made a noise because he smiled as I stood there riveted. The pictures hadn't given a real scale to him. While I was thick, he was thicker. The head the size of a racquetball and the shaft bulged some beyond that. He was semi-hard but as I stared it elongated out at a forty-five degree angle to at least eight inches and maybe more. A pair of heavy balls swayed slightly beneath all of that.

"You appear to be wearing too much now. I'll finish and let's take a look at you." He dropped the robe off his shoulders and stood naked looking expectant.

I kicked off my shoes and unbuttoned my shirt still mesmerized and a little worried about the weapon that bobbed from his thighs. The pants slid down to pool at my feet and I stepped out of them.

"Oh very sexy. Did you normally wear a thong?" I almost blushed and shook my head.

"Well lets see all of you." He moved around me and grasped my exposed as cheek in a stroking motion.

"Beautiful ass. Be a shame to cover it." He moved behind me stroking my bare cheeks and running a hand across my chest and down across my stomach. The hot shaft bumped against me. Worming through my crease I moaned a little as Robert whispered in my ear.

"You're made for loving. For a cock to slide up your ass and fill it. Are you going to let me make love to you? " Both hands pushed beneath the waistband of the thong and pushed them down so my hardening cock popped up. A hand cupped my balls while the other stroked the shaft. All while the fat shaft ground in behind me.

"You're too thick" I whispered. "I don't think I can take that much."

He didn't stop stroking as he spoke. "Have you seen the little starlets get sodomized with a smile on their face? How do you think they do it? Preparation. And that's what I'm going to do for you to get you ready to be made love to the first time. The human body is remarkably flexible. There's people who take fists and other massive things. I'm much smaller than that." He paused.

"But nobody is going to force you. I promise you that you'll love the prep. In fact you can say no anytime and I'll respect it. On the other hand when you're ready to be made love to I want you to roll over, and spread your legs. Then put a condom and lube me up so you can put my cock inside. Is that fair?"

"Yeah, I'm just a little nervous."

"Trust me. I've had to prepare my lovers most of my life. The key will be getting you to relax and that's what we're going to do first. Let's go into the bedroom and lie on your stomach."

I followed with some trepidation but knew that I had enjoyed being prepared my first time. Robert didn't seem like he would force anything and at worst I could give him and handjob and or blowjob.

He was prepared. Lube stood ready with condoms on the nightstand next to a towel covered bed. There was also massage oil warming and he motioned me to lie down.

His hands on my shoulders made me groan and in long oily strokes he massaged me into a puddle. Neck, arms, shoulders, back, legs and then finally my ass. I was spreadeagle by then and felt the fingertips glide up my inner thigh and massage just behind my balls in an oily swirl that took my breath away.

I felt him move and then his thumbs pulling me wide and hot breath. "Every part of you is beautiful. What a lovely tight sheath" and he ended the statement with a long lick that started behind the balls and traced over the wrinkled flesh.

"Uhhhh" came from my throat and he followed with a second swipe that had me squirm. The tongue muscled against the knot some more and my legs twitched at the sensations. More thrashing came as he worked me over and my rod was hard against my belly and the bed.

"Lift up a bit" and I complied not wanting the pleasure to stop. That round pillow that hotels seem to love along with another were jammed under my belly leaving my cock and ball hanging and backside exposed to him. A greasy hand stroked my shaft and balls while the glorious tongue has disappeared to be replaced by the pad of a thumb massaging.

That too felt marvelous as he worked on me and squirted lube over my wet backside. "Here's a single finger" and I felt the penetration.

It didn't hurt and in fact there was no real resistance at the inner sphincter but my whole body went rigid when that finger tapped my gland. "Oh god, oh god" I repeated and squirmed against that probing finger.

"You're leaking. I take it that feels good?" he questioned knowing the answer.

For my part I just babbled because although I had done prostate play before, this was at another level. He stopped and pressed against the taint and I regained mental cohesion. "This is two fingers now."

There was a little stretch this time but again the muscle relaxation just left it a smooth passage inside that the bands of muscles easily gripped without discomfort. I gave a heavy sigh when I realized there was no real discomfort, just the feeling warm flesh splaying my back passage.

"Ughh " the feeling of two fingers stroking the edges causes me to hyperventilate.

"You have a very sensitive body and it feels wonderful to play with. Any regrets so far."

"Nuhh . . .No" I groaned as I rotated my ass up into the invading digits. I actually caught myself whining when he removed both of them and drizzled more lube.

"This is three fingers" and this time I felt a stretch and panted with the tension but could take it. The strum of digits across the gland and the twisting in my widening channel made me purr with pleasure as the other hand kneaded and stroke my genitals.

It was having an effect as I wriggled and I felt myself start to go only to have him stop and press firmly behind the balls again. "Not yet" and he stopped as I panted in frustration. I humped back on his fingers hoping to have that magic spot touched again but he moved them to just penetrate an inch or so.

It was a gentle movement. Splaying and twisting in a smooth in and out. I don't know how many fingers he had me at that point and I didn't care. The internal stroke came with the twist of a lubed hand on my shaft and I moaned long before whimpering. "Let me finish. Please! I can't take it."

"The first time you come needs to be with me up in you, making love. Do you remember what needs to happen?"

The need was so strong as he removed his hands and there was no doubt or hesitation on my part. I rolled over, hips supported by the pillows. Legs back and spread in the classic receptive pose.

"Beautiful. It's almost time. Get me ready." He handed me a Magnum XL condom and the lube bottle.

I stared at the wrapper, turned on like I had never been before. "I don't think we need this. I saw your tests. Have you been with anybody else since then?"

He smiled hugely. "No, in fact I've been waiting for a while now but probably won't last long bare."

I squeezed the lube into my hand and stroked that hot flesh. I couldn't help it and raised up to suck just the tip in before he pushed me away. "I don't want that right now. I want to be inside you. Making sweet love and breeding you."

I lay back down full of lust and staring at him approaching and kneeling between my legs. Stretching I grasped the head and aimed it towards my hole. Feeling the warmth as it pressed at the natural indentation and then tugging him forward so the head pressed in.

I moaned at the feeling. It had been a long time and it was that feeling you only get when something large is going up your ass. I gave an involuntary squeak and he stopped. "You can do this baby. Another inch and your tight little hole is going to flower open. Then I'm going to slide in and your gland is going to drive you crazy. Are you ready for more?"

My lips pressed together hard and I felt his rigidness holding the muscle open while I willed it to relax. I nodded and the press resumed until that moment when we both knew he was in and there was a mutual gasp.

He stared straight into my eyes and forced his hips forward as I felt him glide deeper inside. Robert leaned forward and supported himself on his hands. His mouth hovered over mine and came down against my lips as he slipped the rest of the way up me for my first bareback sodomy.

"See, you can take it. A big cock up your ass for the first time this weekend. Took it like a champ. I'm going to make love to you and make it my pussy now and you're going to come."

He pulled out part way, poised over my gland and gave a thrust to fully embed himself. That was all it took and the second his shaft rubbed the gland I lost it and groaned into his mouth as I thrashed. My cock jerked and spasmed wildly before emptying itself all over my stomach like a firehose.

Robert paused firmly ensconced and leaned back some as my hole continued to expand and contract around him. "That was absolutely beautiful and I'll always remember it." He swiped at the cum that managed to hit his chest in a wild shot and brought the finger to his mouth as I watched. Then he continued with the pools and streaks that adorned me.

Leaning forward again I got his full length as his mouth found mine and shared my emissions in a swirl of dueling tongues. He gently rocked. The slide of flesh on flesh leaving me comfortably sated as the glow of orgasm continued. I wanted him to come in me. To finish things properly with his cum shooting deep up my channel.

"Can I come in you?" he asked breathlessly as he slid in and out."

"Yeah, I want you there. Come in me. As deep as you can." I rocked my hips up to try and accept as much length as possible.

His lips came down on mine again and with on last thrust I heard him groan and felt the jerk before the added internal warmth and added liquid.

We both lay there panting with him still inside.

"Thank you" he said and kissed me. "Am I too heavy?"

"Nope, stay right where you are. I like the feeling." And I did. There was a fullness and warmth along with the feeling of possession. I had let him breed me instead of the impersonal barrier of a condom and was enjoying the connection for the first time.

"Well if we keep this up we're going to go again because I'm loving this body."

"What's stopping you. Love me again. I thought I was never going to be able to take it and you showed me I was wrong. Seems like that gives you an extra play" I said with a smile.

"Don't have to tell me twice" and he pulled my legs down straight and we rolled over with me on top. I was worried about getting squeezed the wrong way but somehow ended up perched on top of him with knees on either side. He was still in me and I could feel the hardness growing.

"Ride me for a while" he said and I did. Raising up until the head barely was contained and then dropping to grind my cock and balls against him while the heavy shaft massaged my gooey sheath.

At one point he came out all the way and I used the opportunity to smear more lube on him before reinserting. Wiggling at the sensation of insertion that I had to repeat a few times. I also marveled at how I could take that thick thing in me.

My thighs started to burn after a while and sensing that Robert raised me up. "Lets spoon for a while." I obliged by moving to my side and purring with pleasure as he moved behind and slotted in. I turned my head back to him and we made out while he gently thrust and jacked me. It was bliss.

"You ok being bred again baby?"

"Can't think of a better place. Fill me up." And a couple of minutes later he did as he pulled another orgasm from me as well. This time he pulled out all the way and I felt so empty for a moment. I could hear him in the bathroom and then he was back with a warm wet towel wiping all the sweat, lube and cum from me.