Icebreaer

Normally I hate these ice-breaker activities, especially at professional conference, but with this table-mate I was willing to give it a try. It wasn't an accident that I sat here. He has average looks but is fit and trim. He looks to be in his late forties or early fifties and takes very good care of himself. His polo shirt is snug around his shoulders and biceps, revealing good muscle tone without being overly bulky. I can see some chest hair where the shirt is unbuttoned. His hair is cropped short and is gray around the temples. It gives him a professorial look. The salt and pepper goatee is carefully trimmed around full lips. He has no ring on his left hand.

He introduces himself as Jack. When we shake hands he holds on for an extra second or two while holding eye contact. Hazel eyes and a warm smile make me want to hold on even longer. He tells me he doesn't like ice-breaker activities but he'll give it a try if I'm willing. I am so willing. Our task is to find ten things we have in common. We find them rather quickly. 1. Single (he's divorced and I'm a widower) 2. Have adult children. 3. Live in the bay area 4. Running 5. Work in technology 6. Read science fiction 7. Hate icebreakers 8.

We meet in the hotel lobby bar after dinner and find seats on a sofa. We order drinks and chat for a bit. The couch is about ready to be replaced. When you sit down you sink a little too far for comfort. When Jack tries to get up to go to the restroom he falls back into his seat and puts his hand on my knee to steady himself. He leaves it there even after he is back sitting. He apologizes and I ask if he needs a push. He laughs that he probably does. As he gets up the second time his hand grips my knee tighter and I put my hand on his lower back and push lightly, letting my hand slide down to his butt as he rises. He says thanks and gives my knee an extra squeeze as he walks away.

When Jack returns he sits a little closer so our legs are touching. After our 2nd round of drinks arrives he suggests we finish them up in his room. I enthusiastically agree and we head toward the elevator. We get in the car and he hits the button for the 10th floor. After the door closes he turns and leans in and kisses me on the lips. My mouth opens and his tongue finds mine. I place a hand on the back of his head and pull his mouth harder against mine. His moustache tickles my upper lip The kiss lasts until the ding lets us know we have arrived. We separate as the doors open. My heart is racing a bit and I am horny as a teenager.

It seems like a mile to his room. He swipes his keycard and pushes the door open. Once inside we put our drinks down on the dresser and start kissing again. He wraps his arms around me and I can feel his hardon against my hip and I'm sure he can feel mine. We stumble toward the bed and lie down without breaking our kiss. We roll over until he is on top of me. We are grinding our hips together and I'm worried I may cum in my pants.

After almost 10 minutes of kissing and dry humping Jack raises himself up on his knees and pulls his shirt off. He is just the right amount of hairy and I run my hands over his chest and stomach as his hazel eyes lock onto mine. I reach up and pinch his nipples and he tilts his head back and groans with pleasure. Then he reaches down and starts untucking my shirt and pulling it up. It is a struggle but finally my shirt is off and Jack is massaging my shoulders and chest, working his way down to my waist. He unbuckles my belt and unzips my pants. I am almost frantic as I lift my butt and help him pull my pants and shoes off. He drops my pants on the floor and I am naked on his bed. He looks down at me with a hungry look and starts running his hands up and down my legs, gently spread them apart as he goes. Soon I am spread eagle and my cock is rock hard and already dripping precum. He runs his hands up my inner thighs and brushes my scrotum and cock with his fingertips, sending chills all over my body. Finally he grabs my cock with one hand and my balls with the other and starts stroking and caressing. It feels like every nerve in my body has been activated at once.

Jack leans down takes my cock in his mouth and starts sucking. He starts with just the head, swirling his tongue around and around while his hands keep working their magic on my shaft and nuts. Just when I think I am about to blow my load he lifts his head. With his eyes locked on mine he inserts 2 fingers in his mouth and gets them wet with his saliva. Then he places them against my anus and starts to slowly push them inside of me. My ass resists at first then they get past the sphincter and a wave of pleasure washes over me. I moan as he slowly finger fucks me, going a little deeper each time. After a couple of minutes he leans down and starts sucking me, this time deepthroating me and thrusting his finger in faster and farther. It doesn't take long before I arch my back and shoot warm cum into his mouth. He takes every drop. Then, with his fingers still deep inside me, pressing against my prostate, he kisses me and my cum runs into my mouth. We pass cum back and forth as we kiss until we have swallowed all of it.

I sit up and start pulling his pants off. When he is naked I start giving him a blow job. He pulls my hips around until we are in a 69 with me on top. His cock, all 8 inches, is in my mouth and throat and he is sucking on my balls. He works his way back toward my anus and soon he giving me the best rim job I have ever had. My cock is rock hard again as he starts tongue fucking me. He is driving me wild. I can't even suck him any more. Finally I can't take any more and tell him to please fuck me, fuck me like a girl. He turns me over on my back and I raise my legs up, spreading them wide. He kneels between my legs and places his cock head against my asshole and starts pushing. He has his hands on my calves and he is watching his cock penetrate me. He is very thick so it takes a good minute and a half before he is all the way in. Initial pain gives way to pleasure as my ass relaxes and he starts slow thrusts with his hips. I have not been fucked in so long and it feels amazing.

After a few minutes he leans down and starts kissing me as he fucks. I wrap my arms and legs around his torso and the feeling of his hard cock in my ass and his soft tongue in my mouth is overwhelming. Five minutes later I come again without even touching my penis. Jack is an energizer bunny and fucks me for another 15 minutes until I feel his body stiffen and with a jerk he explodes in my ass. He continues to thrust inside me and kisses me again. A few minutes later he stops thrusting but he leaves his dick in my ass and we kiss and hug until he goes limp and his penis slides out of me. He rolls onto his back beside me. I feel gooey cum dripping out of my ass and reach down and get some on my finger and bring it to my mouth. Then I bend down and take his limp, sticky cock in my mouth and suck it clean. Once I have l gotten every drop I kiss him again, long and hard.

We lie in bed touching and kissing for quite a while. After about 20 minutes we are both hard again and he tells me to fuck him. He gets on all fours and I return the rim job and tongue fucking he gave me until his ass is slick with my spit. I place the head of my cock against his ass and start pushing against him. His ass is so tight that we stop while he get some lube from his bag. He applies a generous amount to my cock and rubs it in with both hands. The feeling of his slick hands rubbing and squeezing me is exquisite. He gets back down on all fours and I apply more lube to his anus, pushing it inside him with my finger. He moans as my middle finger goes deep inside him. I find his prostate and massage it with my finger tip. I add some more lube and another finger. I twist my hand back and forth as I thrust in and out. Then I add more lube and another finger. I am thrusting and twisting and he is matching my rhythm, pushing back against my hand, trying to get me deeper into him.

I pull my hand out and again put the head of my dick against his anus. This time I am able to enter him after a little pushing. He gasps when my head gets past his sphincter and tells me to stop for a minute. He is so tight I wonder if this is his first time being a bottom. After a minute or so he starts to move his ass back and forth, at first barely an inch but quickly lengthening his strokes. I start to match his rhythm and soon we are thrusting long and hard and my thighs and hips are slapping against his ass. We fuck this way for about ten minutes then he slides down until he is laying flat on his stomach with his ass raised a little and I am lying on top of him, taking long slow strokes. This position makes his ass feel tighter. I kiss the back of his neck and nibble his shoulder and ear as we fuck. He is moaning and groaning and the sound and the sensation of our bodies making full contact, not to mention his tight ass squeezing my cock, is so amazing I want to do this forever.

But after about five minutes I can't hold back any more and I blow my third load of the evening into his ass. We lay, coupled, until my dick softens and slides out of him. I kneel behind him and pull his hips up until he is kneeling and I go down on him again. When my tongue touches his anus it opens obediently. I'm not crazy about the sensation the lube produces on my tongue but I am too horny to care. There is not a lot of cum but I lick up all I can and use my tongue to explore his entire anus. When I am done with his ass I have him lie down and I turn my attention to his cock. It is rock hard again and is dripping copious amounts of pre-cum. I take him into my mouth and start sucking him while massaging his balls, occasionally slipping a finger back into his ass. It doesn't take long for him to climax and his warm cum fills my mouth. I move up and we share another long, slow cum kiss. We fall asleep in each other's arms, smelling and tasting of cum.