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I had many sexual adventures prior to my enlistment, but since this is about my time as a sailor, we will focus on that. Don’t worry, we will cover the other stories at a later date. For now enjoy my story about being an anniversary gift.

After I was given the privilege of leaving base in Pensacola, I started going out to the local bars and drinking. School got out early so I would explore the town a bit then hit up a bar and try to get lucky. A few times I did in fact get lucky. And I mean lucky, like forget ‘out of my league’, more like ‘playing a different game’. Anyway, that’s not the point.

November of 2016 I left school on a Friday, went to the barracks, changed, and got a cab into town. I decided on a bar, then ordered a beer and a shot of Jameson. When the bartender brought them I pulled out my wallet but he informed me they were already paid for by a couple at the end of the bar. I waved at them to say thank you and they approached me. They asked if I wanted to join them at a booth against the wall; I figured that if they bought me alcohol just to speak with me the least I could do is sit with them and let them spend more money on me.

I looked them over and they were a good looking couple. The man was easily six feet tall, broad-shouldered, and narrow below his chest. He looked like he may have been a competition swimmer in college. The woman was much shorter, five-two on a good day. She wore a lavender colored dress that barely revealed enough of her chest to catch a glimpse of cleavage. She appeared to be in fit shape but dressed modestly as to not draw attention to herself.

We sat in the booth and began to chit-chat. They asked the usually stuff: are you from around here? No. (They weren’t either). Why are you here? Navy. (This was their anniversary trip). How old are you? 21. (They were 39 and 42). Why did you join? I was bored.

Eventually the conversation got to their past vacations and the husband got really excited.

“Helen, show Jason our pictures from France!”

“Of course! Jason, you’re going to love these! Here, let me come sit next to you to make it easier.” She got out of the booth from next to her husband and came around to sit next to me. Considering that she was married and her husband was directly across from us made me a little uncomfortable with how close she was to me. Like, her tits were pressed against my right arm type of close. I hadn’t noticed before, but now that they were touching me I decided to sneak a quick glance.

I got one clean look down the top of her dress before she readjusted herself to pull out her phone. She had nice tits. I’m no expert on size, but let me tell you that they were easily too big to hold in one hand. I’m not so sure she was wearing a bra either, because I’m almost certain that I saw a nipple.

She pulled her phone out of her purse and immediately opened it to the photo gallery. She tapped an album labeled “Travels”, then another album inside of that labeled “France.”

She tapped a picture to make it full screen then held the phone up to my face. I tried to be nice and act like I cared about her picture in front of the Eiffel Tower, and another picture from the top of it overlooking Paris, and so on for another four or five pictures until she swiped and I almost choked on my beer.

The picture showed Helen on her knees with two cocks in her mouth. One of the cocks likely belonged to her husband, probably the one below the camera. She swiped again and this time her hand moved over my leg and to my cock. This picture showed Helen on all fours on a hotel bed, sucking the other man while her husband fucked her from behind. From the angle of this picture I could see that she was wearing a butt plug.

I set down my beer and tried to speak.

“Those, uh, those look like a, uh, fun time in Paris.” I looked nervously at the husband, (I believe his name was Thomas, not sure exactly, but let’s call him that for the sake of the story). I looked at Thomas nervously but saw a grin on his face. Helen swiped again.

He was clearly enjoying what was happening.

This time it was a video. She made sure the sound was off then pressed play as she grasped my shaft in her hand. The video started where the last picture ended. fındıkzade escort I saw Helen grab the other man’s cock and point to the bed. The man climbed on the bed and lay on his back. Helen reached behind her and removed the plug from her ass and, with a smile, sucked on it before inserting it into the other man’s ass and mounting his cock.

She waited as Thomas readjusted himself and the camera, then shoved his cock in her ass. They both began to pump into her holes when suddenly the video stopped.

Thomas looked at me and spoke. “So Jason, what do you say we buy you another round and you can join us on our anniversary adventure in Pensacola?”

By now, Helen was basically jerking me off through my pants. “Sounds, uh, sounds like fun.”

“Yay!” Helen quietly squealed. She motioned to the bartender and got me two more shots of Jameson and another beer.

I walked around the town with them for a bit and things got interesting. Thomas clearly enjoyed watching his wife with other people; in fact if you didn’t know better you would think that he was the third wheel and I was with Helen. We would stop to smoke a cigarette and Helen would put her hand down my pants, or grab my hand and stick it up her dress to feel how wet her pussy was. At one point she had grabbed my hand and shoved two of my fingers in her dripping wet hole, then pulled them out and told me to shove them up her ass. I did.

We got back to their hotel room and Helen stripped her dress and hopped on the bed, looking at me and Thomas. I was right, she wasn’t wearing a damn thing under her dress.

“Both of you strip.” She commanded as she began to rub her clit.

We both complied. Both of us were rock hard. Thomas walked forward and climbed on the bed. I began to follow but Helen held up her hand in a ‘stop’ motion. I stopped. She spoke.

“Okay Sailor boy, before we go any further with this I want to set the rules. This is my gift, so I get to be the boss here. When I give Thomas a woman, he sets the rules. Anything I want, I get. You do as I say without question. If you refuse, we won’t force you, but that is the end of our fun and we can find someone else. Hopefully you stick around for the whole weekend. Do you have any questions?”

Before I could answer, she mounted her husband, her back to him and facing me.

“No.” I finally uttered.

Thomas smoothly slid his swollen member into Helen’s ass. She gasped as his (probably 10 inch) cock was buried up to the balls inside of her rear end. She leaned back and spread her legs, then blew a kiss at me. I got close to her and slid inside of her. She was warm and dripping wet. As I inserted into her I could feel my dick rub against his through her pussy.

It felt strangely amazing. It was like I was being massaged while fucking. Helen leaned forward and kissed me. She stuck her tongue in my mouth and kissed me more passionately that any girlfriend I ever had. She pulled away from me and held my face to her chest. I took one of her nipples into my mouth and held it firmly with my teeth while sucking.

She began to grind back and forth, with a man in each hole. Each time she moved back and forth our cocks massaged each other while our balls rubbed together. I was a bit uncomfortable with how close I was to him, but that quickly passed as she continued to ride us. She rode us with rhythm and the three of us gasped and moaned with each movement.

At some point Thomas had pulled out of her ass and I felt his bare cock press against mine. I felt his head slide up my length as Helen’s wet hole suddenly got tighter and she let out a little scream of pain and pleasure. We were now both in the same hole. I was strangely into it. Our slippery cocks danced together inside of her. I could feel his veins with my sensitive appendage, the underside of my penis rubbed against his while the topside rubbed against her.

My moans began to get deeper until Helen told me to stop. I whimpered with the denial of my orgasm, but obeyed her command. I watched as Thomas continued to plow into her, this time back in her asshole.

Helen looked at me and told me what to do next. “Eat my pussy. Now.” I hesitated for a second aksaray escort since she was being fucked, but decided that a weekend of crazy sex was at least worth a possible taste of his cock.

I decided that since I had already felt his balls against mine I may as well go for it. I dove face first into her clean shaven pussy and began to go to town. As I did, I could feel his cock resting now on the side of my face. Thomas had pulled out of her ass and was playfully slapping my cheek with it. It was easily a few inches longer than mine, and covered in pussy and ass juices.

Helen pulled my face away from her pussy for no longer than a second before her husband grabbed his cock and shoved it in my mouth. At this point I didn’t care so I tried my best to take it as deep as I could. I bobbed up and down, doing my best to imitate the best blowjobs I had received. If I was going to suck a dick I was going to at least be enthusiastic and try to do a good job. Nobody wants a blowjob with no heart behind it.

I stopped at the tip and sucked his head while tonguing his dick hole, then pulled it out of my mouth and licked him from his balls to his tip, then tried to take him in my mouth again. I couldn’t deepthroat, so with as much of him in me as I could fit, I still had room ro grip my hand on his shaft. I squeezed his shaft as hard as I could and I felt his slick head swell up in my mouth.

Helen pushed me off and said it was time to readjust. With her back on the bed, she commanded me to get in the 69 position. I began to eat her pussy and she lifted her head up not to suck my cock, but to eat my ass. She was extremely enthusiastic about it. She licked and stuck her tongue inside my asshole, she sucked until it felt like my asshole was swollen, and she was sloppy with it. I could feel nothing but wetness between my ass cheeks and her tongue up my ass.

She removed her face from my ass and took my cock in her mouth. I felt her hands reach up and spread my cheeks. Suddenly I knew what was about to happen. Thomas got behind me and pressed his swollen cock head against my wet and swollen asshole. I tried my best to relax but it didn’t help much considering that I’ve only ever had a finger up my ass during a blowjob.

He didn’t shove it in, but he didn’t go slow either. Pain exploded in my ass as he easily forced his way inside of me. It felt like I pulled a muscle in my asshole. He had to only be about four inches inside of me and the pain was too much. I let out a little scream and suddenly I felt his hand on the back of my head. He pushed my face between Helen’s legs and said “shut the fuck up and eat her pussy.”

With that, he forcefully shoved the rest of his length inside of my ass. This time is was merciless. His balls were pressing up against me before Irealized how deep he was. He pulled out, leaving only the tip inside of me, then slammed into me with his full weight. He repeatedly this again and again, getting faster as he went. Helen took my cock out of her mouth and was now intently watching a close-up view of Thomas roughly and mercilessly slamming balls deep in my sore hole with every thrust. My half-hard appendage now swinging and flopping around uselessly.

As the lubrication from her saliva wore off I could feel my anus gripping his massive cock every time he pulled back. My mind immediately flashed to porn videos I had watched where a girl was getting fucked in the ass and it looked like her asshole was trying to keep him from pulling out. I think I may have seen a sub reddit called “r/lipsthatgrip” that showed what popped in my head. Every time he pulled back, my anus followed and begged him to go back in, then he would oblige.

As he repeatedly impaled me, I could feel a pressure inside of me. Almost as though he was hitting the back wall of my insides with the head swollen head of his cock. It was uncomfortable and mildly painful, but there was no going back and definitely no escaping. Between his hands gripping my hips and her arms locking my legs in place, I was trapped. I was trapped and helpless. My cock was soft and flopping around, I was getting fucked in the ass like a worthless whore, taking every painful inch inside of eyüp escort my once-tight virgin asshole. And I was loving it.

By this point I had stopped eating Helen’s pussy. I could feel the tears of pain dripping down my face. Thomas stopped sodomizing me and when he pulled his cock out, my asshole winked, but refused to close. I felt a slight breeze enter inside of my gaping hole. I thought they were going to let me up but he readjusted. He wasn’t done. Of course not. He hadn’t cum yet. I wasn’t filled with his semen and dripping like a whore yet.

He stepped on the bed and was positioned directly above me but facing away from me. He grabbed his shaft and pointed himself down, then without warning shoved himself inside of me again. Again, the pain of a pulled muscle exploded in my asshole. Again, the pressure against my insides.

This time, however, the tip of his cock pressed almost directly behind my own uselessly limp cock. Right on my prostate. He continued to pound away. This time, the pressure inside of me didn’t ebb and flow like it did before. It built up more and more. My balls contracted and I felt like I needed to piss.

He went on like this for what seemed like an eternity, slamming his painfully large member into my prostate with all of his weight behind it. At this point I didn’t even feel his girth stretching my hole, the building pressure was making my legs tingle and my hips feel funny. Suddenly I couldn’t control myself and I knew what was happening. I was cumming. I had heard about the hands-free orgasm, but never experienced one. Like I said before, I had only ever had a finger, maybe two, in my ass during a blowjob. This was different. This was intense. I was cumming with a flaccid cock and it was the best orgasm of my life.

I felt the orgasm in my entire body as the semen quite literally flowed out of me and landed on Helen like an abstract painting. The feeling was amazing and I didn’t want it to stop. Suddenly I realized that Thomas had stopped fucking me and that I had started bucking into him. I was fucking his cock into me and I couldn’t get enough. I forced his cock into my ass over and over again, I never wanted to stop cumming and I never wanted to have a normal orgasm again.

Helen squealed with delight as she was covered in my sticky white mess. I continued to force her husband’s cock into me as deep as I could manage but eventually the cum stopped flowing and the ‘assgasm’ subsided. I stopped bucking and he started fucking again. Seconds later I heard him let out a moan and shove deep inside of me. I felt him throb as he spurted inside of me. He was stationary for a solid thirty seconds. It felt like a heart was beating in my impaled anus. I was in heaven. He pulled out with a messy, wet sounding plop that almost made me hard again.

Helen gave my ass a little slap. “Sit up on your knees and push it out for me, sweetie. I’m hungry for dessert.” I did as she asked and lifted my body so that I was on my knees with her face directly under me. I could still feel that my asshole was gaping open. Her tongue circled my open anus before she planted her lips around it. I pushed and I could feel the semen being forced out of my rectum and through my gaping hole into her mouth. I continued to push and push. I don’t know how much he came inside of me but Helen kept moaning like a starving refugee eating a Michelin star meal and slurping at my asshole.

When it finally felt like my insides were free of her husband’s fluids, she pushed me off of her and Thomas was on his knees next to her, his cock glistening with cum.

Without being prompted, I leaned down and took him in my mouth, sucking and cleaning the cum off of him. When he was clean, he told me “you made quite the mess on my wife. I think it would be quite rude to make her clean up your mess.”

I understood. Without a word, I mounted Helen and lowered my face to her neck and began to lick my semen off of her skin. I moved down to her collar bone, then to her beautiful cum-covered tits. I licked and sucked and swallowed until the only mess on her chest was my saliva.

Exhausted, sweaty, sticky, and sore, the three of us made our way to the large shower in their suite. We all stood under the water together, rinsing each other off amd playfully touching each other. When the shower was over we toweled each other off and headed to their bed. Helen lay in the center with Thomas and myself on either side of her. Helen spoke up.

“So, are you ready for Saturday and Sunday?”

I looked at her and nodded, too tired to speak, then nodded off.

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