I spend an afternoon with my gay college buddy. He begs me to fuck his mouth. Then I destroy his tight asshole, dumping a big load deep inside.
Chapter 64:
A NEW DILDO
64. Saturday arrived at the Atlanta Ritz-Carlton. I was spending the weekend here in total luxury with three of my college buddies. Still a bit fuzzy from the antics of the night before, I rang up the other suite. Tommy answered, a lilt to his voice. He suggested that we all congregate in their suite for some room service breakfast and to plan our day. Over breakfast we learned that Jack and Al had a golf tee time at noon-thirty. They'd be leaving at noon, back around fiveish. Tommy wanted to do some shopping for trinkets to take back to his family. My mind vacillated between Claire, from the airline, and a nap.
Al and I returned to our suite. He jumped in the shower, so I headed to the lobby. I was hoping I could convince the front desk to give me Claire's room number. Failing that, I'd try the concierge. There must be a way. After all, she had somehow gotten my room number.
"Good morning Mr. Sailor. What may I help you with?"
"I'm trying to contact one of the flight attendants who is staying here. Her name is Claire, and she checked in yesterday, checking out Sunday. Any chance you can share her room number with me?"
"Unfortunately, we're not allowed to release that information Mr. Sailor. But I'd be happy to either forward a message to her or, if you prefer, I can dial her room, and you can take the call on the house phone at the end of this counter."
"Yes, that would be perfect. Call her for me, please."
"Certainly, sir. When that phone rings just pick it up and you'll be connected."
In moments the house phone rang, and I picked it up. "Hello? Claire?"
"Yes, this is Claire."
"Good morning, Claire. It's Sailor."
"Oh, hi, Sailor. I was just talking about you. I was having a late breakfast with some of the other attendants, and we were trading stories about interesting passengers and our encounters."
Jokingly I responded "Oh, great! Now I have an airline reputation to either uphold or run from, depending upon what you said!"
She chuckled. "No, no. It was all good Sailor, very good" she said with a smile in her voice.
"I called to see if you wanted to spend some time together this afternoon. My friends are either golfing or otherwise occupied. I thought we could have lunch and maybe go to a park or something. See some of the sights Atlanta has to offer. You interested?"
"Sailor, that sounds wonderful, but I already have plans for the day. I'm so sorry. Can I get a rain check?"
"Aw shucks. I was hoping to see you today. I guess you'll have to feed me free drinks on our flight back to Orlando as a consolation prize."
"Now that I can handle."
When I got back to the room Al was just leaving. I reminded him that our dates were due to arrive around 8. Then I stripped down and climbed back into bed to alternately watch some TV and nap. Although my Love Boat has a television, I rarely watch it. The occasional hockey game, reports of monumental world happenings, hurricanes approaching are about all I care to see.
As the TV droned on and on, I fell into a slumber. My mind was filled with visions of some of my memorable past lovers. Trixie, Vista, Pam, and clueless Christy invaded my consciousness as it released its grasp on me.
A persistent knocking at the door abruptly roused me. I shuffled to the door to see Tommy standing there, bags of gifts hanging from his hands, a wide smile on his face. "Hey, Sailor. Hope I'm not interrupting anything. I forgot my room key. Any chance I can hang here for a while?"
"Of course, Tommy. You're one of the Fucked Up Four, right? Come on in and make yourself comfortable. I'll get you a drink." Tommy moved to the couch in the living room and settled in. I handed him his drink and sat at the far end of the couch. "I see your shopping trip was successful. Did you find some cool stuff?"
Tommy's eyes lit up, and his face exploded in a cheek-to-cheek smile. "Oh, my God, yes! Wait till I show you!" He was so excited he could hardly contain himself. He reached into one bag and pulled out a dildo, 9 inches and fat. "Look at this beauty, Sailor! I got this for my partner back home but I'm certain that it will arrive already used. And look at this interesting toy - it's a cock ring with this thingy going around to your ass. Double duty!!" He was as animated and excited as a kid in a candy store.
"Wow! Those are nice gifts, Tommy. I'm sure your partner will enjoy them. And maybe you can try out that dildo on your date tonight. Or have him use it on you."
He adopted a somewhat deflated posture, slumping his shoulders forward, his head bowed. "I was hoping that maybe you'd try it on me." His head still bowed, he raised his eyes "Would you? Or is that asking too much. After getting to suck you last night, all I can think about is having you work my ass. I thought this dildo might help."
"I'm flattered, Tommy. Honestly, I am. And to think of the four years spent as buddies in college and I never knew. Think of the fun we could have had if we knew then what we know now."
"Well, I struggled with it in college. I had strong feelings about other guys, most especially you, but I just couldn't admit it publicly. It wasn't until after law school that I found myself. My first job was with a solo practitioner. He was a big, burly figure, a take charge kind of guy. He'd gruffly bark orders at me. Anyway, we had a big case, one worth millions if we won. One night we were at his apartment, ass deep in books, doing research. We had been at it for hours. The stress permeated the room. We both stood up to stretch and take a break. Suddenly, he barked at me "Pull your pants down and bend over!" Caught off guard I just stood there. He ripped down my pants and brutally raped my ass. That was the start of my training to become the sissy bottom that I am today."
I really wasn't interested in taking advantage of my college buddy, yet he was asking, almost pleading for it. "Okay, Tommy. If that's what you want, you'll have to suck me up first." His face lit up as I pulled off my pants. I stood and stepped in front of him sitting on the couch. I took hold of my flaccid dick and spanked his face with it a few times.
"Alright sissy. Be my little mouth whore. Suck me up so I can push my fat cock up your ass." He held my limp dick at the base with the fingers on both hands, like he was holding a Whopper, about to stuff it in his wide open mouth. As he pulled it to his mouth, he used his grasp to tug it fully in, putting my entire soft dick in his mouth. He sucked and used his tongue on it, pulling his head back, licking my frenulum, then stuffing it all back in. His technique was good and the marvelous feelings in his warm mouth had me hard in no time.
He mouth fucked my shaft long enough to loosen his deepthroat muscles, then grabbed my ass signaling that I was free to ram it in balls deep. My hand on the back of his head forced my swollen glans through his ring of pleasure. He gave me free rein, so I tried that ring on repeatedly feeling it pop over the knuckle with each stroke. He encouraged me with his hands, pulling my ass cheeks so that I was slapping against his face every time I bottomed out.
Abruptly, he pulled his head off my throbbing cock. He swiftly dropped his drawers and twisted around onto his knees on the couch. Unbeknownst to me, he had some lube hidden somewhere which he reached around to me. I put a big dollop on his hole and stroked some on my raging cock. As it popped into his ass, he let out a moan sounding as if he had gone to heaven.
"Oh, Sailor. You have no idea how good that feels. I've dreamt about this for years. My ass is all yours, no limits. Give me some memories I can take home."
I took full advantage. I destroyed his tight hole, hearing him moan and groan in ecstasy as I pounded away. I was vaguely aware that he was stroking his own dick as I pummeled his ass. He knelt there taking all I could give for as long as I wanted. With one foot up on the couch and my hands on his hips I entered the home stretch. My thrusts were so hard his whole body was lurching forward. I knew my orgasm was moments away, so I increased the tempo until payoff.
When I stepped back, he swiveled around and lovingly washed my shriveling member. He spent considerable time on my frenulum, sucking and licking, much to my enjoyment.