Opening an Ass for a Friendbyfrezrevup©
"That's Longfellow beach," Jen said poking her finger at the window of the air taxi on its final descent onto our exotic Caribbean island.
"Uh, oh, Kyle," Steve said. "Now we know why your wife came on the trip. How do you plan to match the swinging meat she's going to see there?"
Kyle paid no attention. He fed Julie their four month old daughter a bottle of breast milk. Though we shared nothing in common, I liked Kyle. He was a slight built bookworm artsy guy that taught a few PhD classes and did most of the mothering for the baby. He spent no time trying to be something he wasn't.
I was the outsider in the group. My girlfriend Nicole brought me along with three of her best friends and their husbands. Kyle, Jen, and Julie were staying in our place and the other couples were around the corner in their own suite. Each unit had two bedrooms and baths, a kitchen and living area and its own private pool with outdoor showers. They were built into the side of a hill and separated for complete privacy.
All but me were under thirty five and worked in an office. Jen was the youngest at thirty two but I knew her better than the others. We trained for half-marathons and were planning a triathlon together to get her in shape after the baby. The race was scheduled a month after my forty sixth birthday.
Jen struggled to accept her days as a hard partier were behind her. I dealt with those demons so I tried to steer her in the right direction.
While the rest unpacked, I went for a swim and long run to unwind. Everyone gathered at our place ready to go out when I walked back in.
"Go ahead and go," I said. "I'll take first watch of Julie and have a pizza delivered."
The baby slept while I called for food and beer and showered naked outside watching the sun go down. I must have been out there for a long time. The doorbell rang as I wrapped a towel around my waist.
Julie cranked up the fussing scared from the noise. I paid for the food over her bellowing.
"What's all that mess about?" I asked her then picked her up out of bed.
She more or less just wanted to make sure she was safe. By the time we got back to the couch, she chewed her knuckles dried up and ready to play.
I ate too much pizza and by the second beer I was ready to call it a night. Julie had her bottle. I burped her and she rested herself with deep breaths. I must have drifted off holding her in my arms.
The feeling of air on my upper thigh woke me. Jen picked Julie off my chest and put her to bed. I was so out of it, I didn't move until Jen curled up next to me on the couch.
I'm not a player. I never touched a girl once Nicole and I started dating. I never cheated on my wife when I was married or even a high school sweetheart.
Jen and I got close because of all the miles we put down together but I encouraged her to stop all the partying and settle down. We slapped hands or bumped fists after a race but never touched.
Having her snuggled up like that unsettled me. It made me notice her too.
She was 'girl next door' pretty with long black hair and dark eyes and freckles around her nose. Until her pregnancy she had tiny breasts but they were up in big B territory and she always had a ripe round butt. Standing next to me in a bikini three days a week, I looked but that was the beginning, middle and end of it.
"What's going on, Jen?" I asked trying to wake myself up and move to a sitting position.
"We were at that bar," Jen whispered. "They have this thing where girls get to dance on these platforms and in these cages if they pass a test."
Jen reeked of tequila. She was so incredibly cute when she got a little wasted. I sat up straight and shook my head a little. I needed water. She knelt up on the couch facing me.
"That Longfellow beach, the guys with the huge cocks, to encourage women to fuck them they check to see..."
"I really like you, Jen, but you've got to scoot over a little. Let's not step over a line. None of this is making sense."
"Of course, I'd never want to cheat," she said. "But we're really close friends. I totally trust you to walk the line that's why I want you to fuck my ass."
"Jen, go to bed right now."
"I know about your cock from swimming and I just looked at it. You can fuck my ass until it looks like what they call a 'slut butt.'"
"Where is everyone else?"
"I told them I was lonely for Julie. It's not even midnight. You can only fuck my ass. I'm only going to blow you to get you wet."
Jen was pretty. Her strapless dress stopped about mid-thigh. Her hair was mussed and her lips glossy and wanting to be kissed. It kept getting more difficult to keep from fucking her.
"Go on and go to bed Jen. This is nothing to talk about drunk. I love you sweetheart. Go now and I'll forget this ever happened."
As I turned my head away she pecked my lips.
"I love you too, Craig. Please, will you fuck my ass?"
"Sure, whatever...just go to bed and I'll fuck your ass raw."
My will to resist verged on breaking until she walked out of the living room. I peed, went to the kitchen, took ibuprofen and drank two bottles of water. Jen was a good kid. I remembered how fucked up I was at that age right after my divorce. It bummed me out because I planned to train with her while on vacation. She'd be so embarrassed it would probably take the whole trip for her to get over it.
I sat back in the easy chair and turned on the television trying to decide if I should say something to Nicole. That debate didn't last long. I fell asleep again.
Jen woke me with a kiss. She sat in my lap kissing my mouth and it smelled a little funny.
"You're kissing a well fucked mouth, Craig. My lips are puffy from sucking your cock. Do you like that?"
Jen scooted back and dropped her mouth over my cock and went down until she choked. When she came up she wiped the slobber onto my knob then between her legs. This girl knew her way up and down a dick. As soon as the naughtiness hit, it caused greater concern.
I tried a different tacked.
"Jen, honey, this isn't a porn video and you're nothing like a porn whore. In the real world, I've lost plenty of girlfriends that bled every time I fucked their pussy. A couple had kids. It's not going in an asshole period. Much less one that's never had a cock in it."
Jen bobbed me one more time and came up coughing a little. She slathered her ass then moved up to me.
"Kiss me, Craig. This isn't sex. I just want my ass opened. This is it. I want to feel like a slut one more time for a few days on vacation. I'll have a big loose ass for the rest of my life and you to thank for it."
I noticed she was naked. Everything in me was trying to stop myself. The moonlight coming through the sliding doors filtered illumination on her hard nipples, across her chin and sparkled her eyes. Her lips were full from sucking my fat cock.
I put my hands on her hips to lift her off of me. It did nothing but get me fully hard. All the working out created an devastating compact little body on her. A friend of mine called her a hundred pound fuck machine.
When I stopped moving, Jen scraped the tip of my dick across her tiny patch of black pubic hair, her clit, pushed through her drenched pussy lips and found her tiny butt.
"Jen," I said as the last threads of my will stretched to breaking.
She kissed me and sat down until my cock found the position to enter her.
"Open me, Craig. That's all I'm asking. It's the only thing I'll ask. Open me."
She put her hands over mine and gyrated a few times then backed up and put her mouth on my cock again. Now stone hard, she only got about half in her mouth before she choked and had to come off of it. She slicked my pole and her ass and kissed me and tried again.
"Kiss me back, Craig. Kiss me until you open me," she whispered. "Someone's going to do it on this trip. I'll fuck one of those nasty cocks that fucks a couple hundred women a year. If you care about your Jen, you won't let that happen. Care for me tonight. Kiss me."
I kissed her back for the first time and she got a little wild and sat down on my cock and it opened her the slightest amount. That feeling made her crazy. She bit my bottom lip and pushed down again. She spit into her hand and rubbed her ass. She shoved her fingers in my mouth and used my spit to lube my head.
We were French kissing so deep I lost track for a moment until the head of my cock almost pushed inside. She backed up and bobbed on my cock and spit on it and spit on her hand and put her fingers back to her ass. She grabbed my shaft and jammed it into her hole. Her eyes opened wide and I got my hand over her mouth to muffle her scream.
"Kiss me. Kiss me. Kiss me," she said ravenous for my mouth. I was in no man's land up her ass to the point I couldn't pull out without tearing something but not beyond the rings. It had to be painful. I had no choice but to fuck her. Both in a panic, we rushed kisses at each other and she pulled my hair and I finally grabbed her hips and twisted her down onto me.
"Oh my god, you're inside me. You're inside my ass. Fuck me, Craig. Fuck me gaping open."
"Shhhh, Jen. I'll rip you apart. Sit still now, baby. Don't move."
"You've got to move...I'm dying," she said.
"Play with your clit, Jen and I'll hump your ass."
She rode her fingers while I moved my hips but didn't penetrate any deeper. It went on until she started cumming and I pulled out.
"It went in, it went in," she said. She hugged me, kissed me then kissed the head of my cock. "Fuck me again. I can't stand it. You're going to have to fuck me again. I have to have that fat bastard in me right now."
"It's two thirty. The bars closed a half hour ago. Go to bed."
I showered, brushed my teeth three times and feigned sleep when Nicole came in the room stumbling drunk. She passed out on top of the covers and I listened to Kyle take the worst ass whopping ever dished out by a hundred and five pound woman in a bedroom.
Dawn broke at six. The light awoke me. No one thought to shut the blinds. Nicole laid faced away with her head at the edge of the other side of our king sized bed. Her dress was bunched around her waist. She must have passed out trying to take it off.
Jen walked into our bedroom naked. She had her cute flat belly back, her breasts were perked up and full of milk. She looked wanton as she slipped around the bed. Before I moved she climbed on top of my legs and sucked my morning wood into her mouth.
"Your cock is punching my mouth open as wide as I want my ass to be. I can gobble you now," she whispered before kissing me. "Shhhh, we have to give wanting kisses, Craig. Look into my eyes and kiss me showing me how much you want my ass."
With my girlfriend little more than arm's reach away, Jen went back down and sucked me in her throat and came up slobbering. She lubed her ass then positioned over me.
"I'm just going to rock you into me, Craig. I've got half a bottle of Astroglide in my ass."
She looked me in the eye and gave a tiny wanting kiss and pressed a tiny amount. It didn't feel like I'd opened her at all the night before. She had both hands on either side of my face and rested her forehead on mine waiting for me to reciprocate.
When I put my hands on her hips she moved and kissed me again. With subtle undulations and ever more insistent wanting kisses, I worked my way to the point she would open. Jen put her fingers in my mouth then to her ass and my head and I passed inside her again as she bit her finger to stand the feeling of it.
This time she was slippery inside and my cock moved easier. I worked in a few inches until the tightness and the kissing put me to the edge of cumming. As soon as she sensed me pulse inside her she moved up and I plopped out.
"You can't cum in me," she whispered.
The first wad of cum hit her under the chin then across her tits bouncing off onto my throat. I sprayed all down the front of both of us. I'll never get that image out of my mind of my cum splashing her tits and the contours of her ab muscles.
She ran out the slider. I heard the shower start flowing. I followed her and stood in front of the other showerhead quickly washing the cum off me avoiding any glance in Jen's direction. Another minute later, Nicole walked out on the patio naked except for her thong and the dress around her waist.
"Oh, yes," she said. "This is the perfect hangover remedy."
Nicole stripped and started off under Jen's shower then moved over to mine after gulping down two mouthfuls of water. I took a gulp and she came over and kissed me.
"Morning, baby," she said. "I'm sorry about last night. We got wasted."
Jen and Nicole talked about the night and the place where girls wore thongs with assholes so big the string disappeared into their ruined asses like it did in their pussy.
"You've got to go see it, Craig," Nicole said. "You could park a car in some of them."
Nicole looked down at my cock then at Jen. "I guess the secret is out. That's what my poor little ass would look like if he got near me with his horse cock."
Jen shrugged, "It wasn't any secret. He's been nearly naked in front of me for two years. It's no big deal."
"Are you still up for Longfellow beach this morning?" Nicole asked her.
"Let's get Julie going. Kyle seems a little out of it. He'll watch her. Are you going Craig?"
Longfellow beach had to be the world's weirdest tourist attraction. There wasn't a room on the island less than a thousand dollars a night but the beach was covered with gawkers.
Jen and Nicole wore the uniform, thongs and a smile. Lea and Jana went with skimpy bikinis. I was no match for the knee slappers standing up at the edge of the bluffs and down along the water, but they had to have been hanging weights off their cocks to get them that long. I had the typical white guy big cock that swung six inches then lengthened out to over ten fully hard. Steve and Rob wore board shorts.
There were two or three sluts laying out at the feet of each guy standing in the bluffs. A bunch of typical porn whores with saggy looking pussies and blown our buttholes. I saw plenty of it in the whorehouses in the Far East as a young Marine.
"That is so disgusting," Lea said. "What's worse, lying underneath the nasty cock that opened them or the ones dancing around on stage last night?"
"I kept wondering what was going to fall out into my drink," Steve said to support his wife.
"I thought I was going to be self-conscious about my tiny tits," Nicole said. "But I've got as good a body as any of these other women."
"I like what I'm looking at," I said walking behind her.
"Ok, we've seen it," Jana said. "Let's get back to the resort so the workout bunnies can do their thing then we can all go to lunch."
Jen turned to me and smiled.
"Wow, I completely forgot about working out, Craig. What's on the agenda?"
Back at the suite, I changed and visualized my workout and cleared my head of everything else. Jen came out onto the patio in her same old suit with her hair braided up ready to swim. She was Jen again.
It was a spectacular morning. The forever blue sky, the jagged cliffs down to a white sand beach and the water so clear neither of us could resist the challenge of swimming the little bay beneath us.
Jen and I worked ourselves down the cliffs. She used my shoulder a few times for balance as we picked over the rough path and we talked like we did before my cock went up her ass. The closer we got the greater the excitement at getting the chance to take the challenge.
"How far is it across?"
"I'm guessing around five hundred meters," I said. "Let's agree on one lap. No sense killing ourselves."
"Can you imagine living here? A life of working out in this kind of beauty...Look at all those fish."
I got a little distracted watching Jen put on her swim cap. The thought that I'd fucked the virgin ass of this beautiful girl fourteen years younger than me came back into my head.
"You're freaked out," she said.
"I love you, Jen. I feel horrible about this. Why do you want to look like a slut? You're so wholesome and pretty."
"I hate that, Craig. Everyone says I look like the girl next door. I want to be wild and draw out that primal thing that comes rages in guys when they see a slut. Do you know how many guys I've fucked?"
"It doesn't matter, Jen. You've got a baby and a new direction."
When I started off into the water, she ran around in front of me and stopped me by holding my waist. "Tell me you didn't enjoy it? Don't play the martyr, Craig. I felt you wanting it. We saw how much you enjoyed it in that explosion this morning. If Kyle had a cock your size this wouldn't be happening."
"Let's swim," I said.
Jen put all her effort into the swim. She challenged me and the competition led to a great time. The exhilaration kept us pumped up all the way back to the patio. Jen stripped off her suit and I followed.
"It was like snorkeling and working out at the same time," she said as she started washing her hair.
The setting blurred everything. I was standing outside with a married woman that just stripped naked in front of me and I was naked too. The suds ran over her hard nipples and breasts and down between her legs. Jen kept a small patch of long curly pubes over her pussy. Her body was back to the same shape as before the baby but her hips were set out a little wider. I'd been the first man in her ass.
"You were smoking on the way back," I said. "I think you got faster by having the baby."
"Quit looking at my hips, Craig," she teased. She jutted her hip at me.
"They look great. You should be proud..."
"You should be proud, too," she interrupted looking at my cock. "It's getting me so wet knowing you want my ass."
She reached out a soapy hand and grabbed it. She came up through the rush of water over my head and kissed me.
"Get up my ass right now. I can feel I'm still open. This is Eros soap made to lube me. I want you to fuck my mouth open too but we don't have time."
At this point, I had no will to stop her or me. I wanted to fuck the shit out of Jen's ass. I thought of those slutty whores on the beach with their assholes swallowing the string of their thongs, I couldn't stop thinking about Jen's little butthole getting fucked by my cock.
We were in paradise. People were walking around naked. We showered naked. I was all jacked up after the workout. It's not an excuse, it's what happened.
The soap made her slippery. I turned her away from me and put her up on the concrete ledge and when she stood on her toes I had perfect position but struggled to get in. All pretense of resisting gone, I held her still with one hand, grabbed my cock and shoved it up her ass. I plowed into her this time more than five inches.
She let out a squeal that echoed across the bay. I pumped her four or five strokes pushing to get to the balls but it would not go. She got a little panicked from the pressure and tapped my hand a few times in quick succession. Her ass tightened on me once and I almost exploded inside her before I pulled out.
I shot all over our feet as I steered her back under the other showerhead. The tightness and the feel of her ass was so fantastic, I could not hold off. That incredible sensation of sliding that deep into her caused my chest to heave harder than sprinting to the finish in a marathon.
My hand held the wall as I heard the sliding door open.
"What happened?" Kyle said peeking out the door holding Julie.
"I thought it was a snake," Jen said. "Those little lizards are all over the place."
She shut off the shower, wrapped herself in a towel and started inside.
"Are you ok, Craig?" Kyle asked. "You look more shook up than Jen. A big former Marine scared of a little gecko?"
I followed in with a towel around my waist.