Hooking Up with Bob

Bob and I had been chatting for about a year now, on a private Discord server. He was just about as curious about same sex relationships as I was. He was only about five years younger than me, and both of us had thought ourselves to be straight, most of our lives. I had been curious since a young age. Having had near experiences now and then that made me wonder. Not to mention I was one of those youths that always thought about how great it would be if I could suck my own cock.

Bob, on the other hand had been strictly straight, and only recently begun wondering after watching some Trans Porn. Chicks with Dicks fascinated him. Then he began to wonder what the difference would be if it was just a guy, instead of a guy transitioning.

We'd traded fantasies and what we thought it might be like. I had related my experience in having had experiencing being pegged by an ex some years ago. In case you're wondering, 'Pegging' refers to a guy being fucked in the ass by a woman wearing a strap-on dildo. Yeah, I'd allowed it, so I could fuck her in the ass. I can't say I hated it. As a matter of fact I kind of enjoyed it. Which only fed into my desire to feel the real thing. I even told Bob, that I'd been wanting the real thing for a while now.

We'd shared pics of our equipment and drooled over the thought of tasting each other and fucking each other. Even had a mutual masturbation session over Discord. I even got him to buy and try one of my favorite masturbation toys. A vibrating cup that fit over your cock and massaged you like a mouth. It got to the point that I'd begun having dreams about him. Even fantasized about my first time being fucked by another guy, being him. How it would feel and how I'd react.

We lost touch for a while. Then one day, out of the blue, I got a notification on that Discord server, that I hadn't logged into since the last time I'd chatted with him. He was on a business trip out my way, and wanted to know if I'd been serious about meeting. Ok, I admit it. Panic set in. I didn't respond. Would he go away if I didn't answer? Then I began to wonder again, what if I did respond, what would happen.

Finally, only a few days after the message came in, I responded to him. I told him I was serious and asked when and where he was planning on being. He forwarded me his itinerary, and asked me to let him know exactly what part of it was closest to me. I gave it a once over and found he would be staying at a Hotel about a mile from my house, two weeks from now. So I relayed that too him.

So the plan was set. We'd meet the day of his check-in and have lunch. Anything more we'd discuss over lunch and plan out from there. From that day, until our meeting, I was on edge. Nearly having panic attacks daily, and masturbating furiously to calm myself down over and over. This would happen, I thought. One way or another, this would go down and I'd finally feel what I'd been wanting, for a very long time.

On the morning we were to meet, I spent an inordinate amount of time on hygiene. Showering, shaving. All over. Even had the presence of mind to do a few enemas and clean myself out from the inside as well. Pocketed a handful of condoms and eventually headed out to our meet up. I arrived at the iHop in front of the Hotel and upon walking in, was flagged down. Bob had recognized me as I came in.

"Dave!" he called out across the restaurant. "Over here." he gestured. So I walked over to the table and held out a hand.

"Bob." I began. "Good to see you." Casual, nothing different about meeting anyone else, I thought. No need to get weird about it.

"I ordered already." he confessed. "Do you want anything?" I told him I'd had a late breakfast, and coffee would be just fine. I suppose, if I was honest, I was too tied up in knots about meeting a guy I would be having sex with, to eat. I'd probably puke it all up.

The whole conversation was pretty G-Rated. But there were a few comments, made under his breath that he just couldn't keep inside, I suppose.

"I just have to ask." he said in a conspiratorial whisper. "You really thought my cock was that good looking?" I'd almost had a swig of coffee in my mouth, and coughed one pulling the cup back from my mouth.

"Yeah, Bob." I responded in a low voice. "I really do." and explained, as I had the first time he'd uploaded a picture of it, that it was what I considered the perfect shape and length. I could see the smile on his face as he just nodded and shoved another bite of sausage and pancake into his mouth.

From there, the conversation was light, and eventually he said. "So, I don't have any work until tomorrow morning." His tone casual. "The company isn't tyrannical enough to put my to work the same day I just drove five hundred miles." he finished with a small chuckle. "You got anything going this evening?" he asked and looked up directly into my eyes.

"Not a thing." I replied. Sensing where this was going, and bracing for the question.

"Care to spend the night?" he asked. Well, I wasn't quite ready for that. I had been expecting something along the lines of 'wanna fool around this afternoon?' Somewhat surprised, I cocked an eyebrow at him and then grinned.

The next words out of my mouth were not intentional, but would set the tone for the rest of the night. Without conscious thought, I confirmed to him, everything we'd talked about in regard to my desires for trying a same sex relationship. My desire to be the bottom. I'd topped so many women, I'd given anal sex and hadn't felt much difference from woman to woman. But the experience of them doing it to me was new, and I'd told him I wanted to try the real thing. And so I answered in a very smart ass tone.

"Why Sir,!" I said, puffing out my chest. "Just what KIND of lady do you think I am?"

Bob laughed, and said. "So, that's a yes then?" I just grinned, lopsidedly, and nodded.

At that moment, I was really aware of what would happen, and still had some reservations. But I was into it now and the apprehension was turning to excitement, and I found I was looking forward to seeing what the evening had in store.

With the check paid, e went up to his Hotel room, and put out the 'Do Not Disturb' sign.

"Join me for a shower?" Bob asked. And now was the last chance to back out. But I didn't. In answer I just began stripping and laying my clothes over the back of the chair in the room's closet. Bob grinned and did the same.

I had seen pictures of Bob, prior to this. But standing this close in the shower, I got a real closeup of what was only a picture on a computer monitor, prior to today. Ok, I'd been in showers with other guys in my life. Back in high school, when I had been a volunteer for a fire camp in the national forest for a season, at the gym. But this was very close quarters and the warm water only helped intensify the heat coming off both of us.

Bob reached out a hand and rested it on my chest. I looked up at him then saw his gaze drop. I felt my cock twitch as I realized he was looking down at my package. Then he looked back up in a questioning manner. So I nodded, and closed my eyes. The palm of his hand was kind of rough, but the water allowed it to slip smoothly over my chest, and down over my abdomen.

He stopped briefly just below my belt line, and my cock twitched again. Then I felt his hand wrap around my length. Now, I'm not a big guy, but I'm not tiny either. When I'm hard I'm about five and a half to six inches long. I'm circumcised and my shaft is pretty smooth. The head is slightly oversize and really quite sensitive. Bob's hand fit around my shaft from the base to the head and the head rested in the crease between his thumb and forefinger.

I gasped as he held me, and I throbbed again. I felt something wet drip out of the tip. A little precum? It all felt really good. Almost the same as me holding my own, but different. A different heat and grip. Then he began to stroke. The pressure squeezing the head of my cock each time he moved forward and back. I gasped after a moment then sprayed a load of cum all over his hand and his thigh.

I gasped and leaned back against the wall of the shower. I knew I was smiling when I said. "Sorry." and took in a sharp breath. "I haven't had someone else stimulate me in years."

There was a sudden heat, close to me, and I opened my eyes to see Bob, leaning in. "Did you like it?" he asked. His face only inches from mine. I had a sneaking suspicion what he was angling for.

"Yes." I replied, and a moment later, his mouth was pressed to mine and his tongue was begging to dart in past my lips. At that point, I simply closed my eyes and let it happen. We only stayed that way for a minute or two, before he pulled away and said. "Let's dry up and go over to the bed." And so we did.

As I sat on the bed, Bob asked. "So, you've never actually given head to a guy?" I shook my head.

"My ex would make me suck the dildo, before she fucked me." I admitted. "But it wasn't really any different than I would imagine a rubber ball would feel."

Bob gestured to his cock, which was mostly flaccid, though I could see the beginnings of an erection, as it twitched a bit. In pictures, it looked about six inches. But now I could see that once he was fully erect, it would be about seven and a half. He was also a bit thicker than I'd thought, based on the images. But, hey. No big deal. My ex had done me with a nine inch dong.

I reached out gingerly and let his length rest in the palm of my hand for a moment. It felt hot. Hotter than mine ever did. And it was bumpy and veiny. As I wrapped my hand around his shaft, it sprang to life and become hard almost instantly. I knew he was circumcised as well, but the head of his cock, flared out a lot more. Mushroomed all around. I had been right about him being longer and thicker.

I sat one the edge of the bed and gently pulled his cock toward me. "Can you be patient with me?" I asked.

"Take your time Dave." he said quietly. "This is new for me too." he looked up and then continued. "I may go off like you did. First time being blown by a guy, and all." he admitted, and gave a soft chuckle.

Well, he really did not go off as soon as he was in my mouth. Though a fairly large drop of pre-cum dripped onto my tongue. But, I'm getting ahead of myself here.

I lifted his cock and pressed the head against my lips gingerly. I couldn't help reaching under and tickling his balls, the way I liked to do to myself when masturbating. Bob hissed then breathed out heavily. His cock jumped to attention, now fully erect, head resting on my lips and I opened my mouth just enough to admit the head, then closed my lips around the head and sucked in my cheeks.

This was a weird sensation for me, and I could feel saliva building up in the back of my throat suddenly, so I swallowed, hard. That had probably been the wrong thing, but it drew his shaft into my mouth and I felt the head bump against the back of my throat, and I gagged suddenly and grabbed his hips to stop him from moving.

"Holy shit man!" he wheezed, suddenly. I pulled my head back, and him out of my mouth.

"Reflex!" I gasped. "I tried swallowing my own spit." and I shook my head. I gazed back at his cock. It was covered in my saliva and glistening. I couldn't help but want it back in my mouth at this point, and slowly slipped him back in. I gripped the base of his cock so that I couldn't take more than half of him in, and sucked in my cheeks and began moving my head back and forth along his shaft.

Each time I felt the head of his cock touch the back of my lips I'd push forward again, until I had built a rhythm. I could hear him panting with each stroke. His cock began to throb with each stroke as well, and I guessed, just as he croaked it, that he was about to shoot off.

"Fuck Dave!" he croaked. "I'm gonna cum!" and he wasted no time. A stream of hot liquid hit the back of my throat, and I took as much as I could then pushed him away. The rest of his load sprayed all over my chest. I swallowed, hard, gulping down what was in my mouth. I'm not sure what I expected, but I'd tasted my own cum on many occasions. My Girlfriends all used to love to snowball. His was a little saltier than mine, but still not objectionable.

"Sorry." I croaked after swallowing. It was just a bit much. But Bob just smiled down at me.

"That felt pretty good." he said with a grin. Then looked down at himself. "But it doesn't look like I'm done." he said, and passed my a towel. Then he reached for a condom on the night stand and opened it. "Do you want to go on?" he asked. "I mean, you did say you wanted a real cock inside of you?"

"Yeah, I did." I said with a smile and pushed back and laid out on the bed. Call me old fashioned, but I do prefer missionary, even when my ex did me.

It had been about ten years now, since the last time I'd been pegged. Now, I have used dildos on myself since then, but that's nothing compared to someone else driving it in and out of you. So I fully expected some pain. Pain I'd had before. But this time the feel would be different.

So, as I lay back, I grabbed some pillows and shoved them under my ass. Then I bent my knees and spread my legs apart as far as they would go. Bob climbed up and knelt between them. He was panting. His cock was still rock hard and the condom encasing him was glistening with lube.

"This'll be cold." he said as he reached toward me. Two of his slicked fingers pressed between my buttock and fumbled around before finding my puckered anus, and pressed. The coolness felt kind of good as he swirled his fingers around inside of me. Any discomfort I'd been expected, just didn't surface. Instead, I felt a shock. A slight electric feeling that went straight up my back and gave me a shiver. Bob noticed.

He smiled down at me as he finger fucked me for a minute or two. "So, it's feeling good?" he questioned.

"It feels wonderful." I replied. "I can't wait for the main event."

With that, Bob removed his fingers and closed the distance between us, until he was between my legs and his cock rested on my balls, gently throbbing as it sat there. "Can you not force yourself balls deep in one stroke?" I asked him.

Bob nodded down to me. "No problem. I'll go nice and slow." he promised.

"I really want to feel every inch as it slides in." I said. "I've thought long about what all those veins and ridges would feel like inside of me."

Bob seemed taken aback by my admission, and just nodded. He pushed the head of his cock down between my buttock and rubbed until he found the throbbing sphincter that he'd stretch out to allow his thick member, entry into my rectum. I took a deep breath, and Bob pushed a little. I felt the mushroom head of his cock forcing my sphincter open. As he opened me wider, I began to feel some pain, from being stretched more than his fingers.

I bit my lip and grunted. Then, suddenly, the pain eased as his glans popped through and settled inside my anus. That was where he stopped and looked down at me. "You're pretty damned tight." he observed. "And you feel fantastic."

All I could do was nod and moan out. "I'm ready for some more." and immediately felt Bob's cock slide deeper into my rectum. It moved slowly and I felt the throbbing and the heat and gasped a few times as he slowly, sank deeper into me, until I felt him bump up against me. He had taken several minutes to sink in fully, as I had requested and I clenched his cock with my muscles.

That was when he fell down onto my chest and forced his arms around my shoulders. "Holy shit man!" he whispered into my ear. "This feels amazing."

"I'm certainly digging this more than a plastic dong." I huffed in short breaths. "I'm feeling the heat, and all those wonderful veins and throbs." I grunted and giggled slightly. "I think, I'd like you to fuck me a little faster." I requested.

Bob simply arched his back and his cock drew back out of me, then suddenly slammed back in. He increased his speed with each stroke, until he heard me grunt each time he hit bottom. He maintained that rhythm for a while.

"Oh My God Bob!" I Huffed. "Yeah, That's good!" I forced out again. "Fuck me like that!" I demanded.

"Oh Fuck!" he grunted through gritted teeth. "Take it all Dave!" he said. "Take all of my Cock!"

I clenched again then thrust my hips up to meet him. "Keep fucking me like that Bob!" I demanded once more. "Give me all of that beautiful cock!"

At that he clamped his arms tighter around me and grunted into my ear. "You really love my cock." he panted. "Tell me you love my cock!" he demanded.

"Fucking A Bob!" I yelled out loudly. "I fucking love your cock! I confessed. "It's better than I imagined, I can't get enough!"

That caused him to slam his cock deep and hold it there. My own cock was rock hard and throbbing against his belly now. He sat back on his heels and pushed himself in and held it there. Then he began to tickle my balls and stroke my cock. I began panting and bucking my hips upward. That only pressed his cock deeper for a moment until my hips came down, and I grunted and squeaked each time.

Just as I felt my own orgasm rising, I said. "I can't take it anymore!" my voice was becoming ragged. "I'm gonna fucking cum any second!"

Bob released my cock and wrapped his arms around my thighs and began pulling me toward him, then pushing back. Thrusting his hips as he did. "Tell me again how much you love my cock!" he demanded. "Tell me how good it will feel to cum from my cock inside of you."

That was about the time that his slightly upward thrust, hit a lump inside of me, and I felt an electric shock surge through my body. I'd heard of a prostate orgasm, but never actually felt one. This caught me by surprised and I yelled and came in buckets. "Holy Fuck!" I screamed. "Oh God Yes!" the expletives just kept coming. "Fuck me Bob! Fuck me faster! Fill me up!"

Bob grabbed my hips and pulled me in. then with a grunt, I felt his cock expand inside of me. It felt for all the world as if his girth doubled and I gritted my teeth as I felt a hot flood splash my insides and begin flowing and leaking out around his length. I kept bucking against him until my own orgasm subsided.

When it all subsided and I lay back panting, I felt his cock begin to shrink inside of me.

"Holy shit man." Bob exclaimed. "You really fucked me dry." he observed.

"You hit my prostate, man." I admitted. "I couldn't stop coming and every time I moved you just got deeper in me." I explained. The more I lifted my hips from orgasming, the deep his cock felt, the more he pressed against my prostate, the more I came, etc. It was a vicious cycle and I was well and truly spent.

You'd be forgiven for thinking that was a good ending. It certainly left me breathing hard and that whole thing only took a little more than an hour. It was now early evening and we got washed up and dressed again. I offered to pick up dinner, but I got to pick the place. I was in the mood for Japanese. The one good Japanese restaurant in town was, thankfully, not busy tonight.

We dined on good food and chatted about the afternoon. Keeping it quite, so not to disturb or offend the other patrons. Bob was very interested in how I felt during the whole session. The subject would soon come up, that, even though he'd gotten a sort of blowjob from me, he hadn't gotten fucked himself. Now that he'd fucked another guy, he wanted, even more to know how it felt.

After dinner we went back to the Hotel. Bob was certainly impatient, because he was out of his clothes before I had put the Do Not Disturb sign out and locked the door. I motioned him to the bed, and had him lay down. He looked at me curiously.

"Relax. Let me do my thing." I said. "I'll make sure to give you the same considerations you gave me."

Bob just grinned, and said. "Take me, I'm yours."