Tunisian Vacation

Bobby was my best friend since childhood. We lived in the same street and saw each other nearly every day. We grew up in a Christian dominated and conservative community which I sometimes resented more than Bobby did. I never had much luck with the girls and being held back by all kinds of rules of courtship and not having sex before marriage made it not easier for me. Bobby did not face that many problems since he was fit, muscular and good looking with sandy brown hair and olive green eyes which sparkled when he put on his smile. And he smiled a lot. I was just an average Joe compared to him, and not only when you took a closer look at me, it is actually my name as well.

But as with all strictly controlled communities the truth behind the façade was often different. We were young hormone-filled boys, I was still 19 while Bobby had already turned 20. While on our hikes and bike-tours we almost always discussed girls and what we found attractive and what we jerked off to. Jerking off was not OK too of course in our community, but nobody really enforced that because you have to vent somewhere. With girls on the other hand you had to be careful. Most of them seemed very devout, their parents often even more controlling and even the ones that Bobby courted were to let him get more than a few kisses. I never even got that far which often frustrated me. But Bobby was always there to cheer me up and find time for me even when a new girl was all the rage for him. He told me everything that went down or not with her and it comforted me that he valued our friendship so deeply.

With all our bottled up horniness and no other possibilities our intimate friendship just had to develop to a stage where we started to jerk off together. Talking about girls was no longer enough so we discussed everything we would like to do to them in detail, telling each other our fantasies and getting ourselves hard. We watched porn together and found time almost every day to "relax" together. It was mostly Bobby at first who drove our friendship in that direction but with time I realized that it was not so much the fantasies and stories that got me hard but rather watching Bobby stroke his 8 inch cock next to me and squirting his huge loads into the air and onto his hands and belly.

I hinted at that from time to time and when we were both horny and stroking our masts he too felt the same way. I was insecure about my dick since it was only close to 6 inches fully hard but Bobby time and time again assured me that he too found me attractive. We danced around the subject for a long time not wanting to admit to our gay or at least bisexual tendencies and having guilty feelings because of our Christian upbringing. Nevertheless the incidents occurred more frequently that we not only jerked off together but that I jerked off Bobby or the other way round. We still pretended to talk about the girls we found hot but in reality we slowly explored more and more of each other's body. First it was just the hand, then rubbing our dicks together pretending to both fuck a girl at the same time, then we mixed our cum and used it as lube on the other ones cock. We came on each other's belly and feet always pretending it was not gay, always feeling guilty afterwards.

After becoming nineteen and having more privacy things got even further when on a few very hot occasions we gave head to one another. Bobby felt way more guilty about it than me and after it happened we usually went back to just jerking off next to each other for weeks because of his guilty conscious. It was not that he was more devout than me but maybe he was not as submissive or it was because he almost always courted a girl at the same time. We had the agreement that our jerking off together was not cheating because we were so close like brothers and it was just our special bond, nothing to do with any girl. But sticking your cock into another ones mouth somehow was too much for Bobby even so.

I on the other hand lost more and more of my guilty conscious with every time it happened and I craved more of Bobby's cock from day to day. I wasn't even interested in girls anymore. I just wanted to serve my best friend and watch him let loose in anyway on my body. In the beginning it was Bobby who headed our friendship in that direction but lately it had become mostly me begging him to serve him more than with just my hand or my fantasies. I managed to coerce Bobby to let me suck him off more often than he sucked me off. I convinced him that it got me off so hard and that he didn't have to have guilty feelings about it or reciprocate. I was fine just to see and feel him cum in my mouth and it made me happy. Slowly he gave in and it happened more often and he even started to snuggle up to me when we had a sleepover and we lay there naked hugging each other without feeling too much guilt at all.

We also frequently went on vacation together since his girlfriend's where not allowed to go on a trip with him alone unless he would have seriously considered marrying them. Nobody batted an eye on the other hand when two guys went on a "culture trip" abroad. Those where the best times. Sharing a hotel room. Sleeping next to each other every night of the trip. Usually the boundaries dropped more and more on such trips and this time should be no different.

We were on a summer vacation in some all-inclusive resort in Tunisia. My plan was to get Bobby drunk enough so he would agree to go even further with me since I craved to feel his fat pulsing cock inside my ass for a long time. I practiced alone with a dildo imagining how it would be to be taken by him. It was something that was yet off limits for him. We got close once or twice but he got cold feet at the last moment and we never got around to it. I was pretty certain that this trip would finally be enough to make Bobby fuck me and once he had felt how good it was he would not be able to withstand me.

It was a very hot and humid summer and the first few days we had difficulties to acclimate to the temperature. That meant that except for early morning and late evening we would spend a lot of time in the air conditioned hotel room with nothing much to do but watch porn and jerk off. Since we also shared a bed at night rubbing our naked bodies together we so far came close to fucking twice when I sensed his hard cock in my back and tried to shove my willing ass in his direction. As long as everything went slow and subtle it seemed to work but every time at the last moment Bobby turned me around so I was facing him and just frotted his cock against mine.

At least he was so horny at that point that he mounted me and even kissed me with tongue when he got close to cumming. On our third day we found our rhythm. In the morning we got up, went for a workout or a run around the hotel grounds, then shower, breakfast, pool. The sun and beach and having nothing else to do helped to just think about sex most of the time. The tan I developed made me more confident in my body fueling that even further. At noon we retreated to our darkened cool room jerking off together mostly next to each other sometimes jerking each other. Because of the heat we dosed off afterwards and in late afternoon we went to the beach and then to dinner and one of the bars of the resort. Afterwards we would snuggle up naked in our beds and all of the time the feeling of our hot naked bodies made us hard again and we played around with each other.

On the fourth day during our midday session I started to plead and beg for Bobby to try and stick his cock into my ass. He told me he couldn't that he had to call his girl every day and that it would make him feel guilty as hell. I tried to convince him that he should just see me as an outlet to release his pressure, that I would be happy to do that for him, that he didn't have to feel guilty. I was squirming and whining like a bitch in heat and although I made some progress Bobby still said no but at least he let me suck him off even at noon from now on. We were here for three weeks but already I was getting anxious that the time would be too short to reach my goal.

Yet that evening we had a very good time at the dancefloor bar of the resort and Bobby had a few to many shots. When we got back to our room I had to hold him upright and help him undress on our bed because he was so wasted. I guess he just played it a little too since he usually can stomach more booze than myself and I knew it was not that much that he had. Of course while undressing we started touching and because of his pretended clumsiness I fell over more than once landing in his arms. We both felt our hard bulges rubbing at each other knowing like in a dance what had to come next. When we were finally both almost naked with just our boxer briefs on we lay next to each other catching our breaths and I stared in his sparkly olive eyes which got illuminated by the small lamp on the night stand.

We stared at each other for a long time and I dared to inch forward and slowly kiss Bobby on his pink lips. He didn't resist and just smiled back. Briefly letting his tongue slip into my mouth and then giggled.

"You really think it wouldn't be cheating?" he whispered in my direction. My heart started to pound. I knew exactly what he was contemplating. I let my hand wander down to his boxer briefs and slowly caressed his growing bulge through the fabric. I licked my lips.

"No. No it would be no different than anything else we do. We are like brothers. We have shared almost everything. I would be happy to do that for you and as with everything else you don't have to reciprocate." I noticed that I started to ramble and not wanting to shy Bobby away from his own thoughts I fell silent again. Another few moments went by with him holding my arm while my hand caressed his bulge.

"Wouldn't it hurt? I mean I don't want to hurt you Joe!" Bobby's voice sounded concerned but also comfortably horny. I could feel that he just needed some final confirmation but that his own inner barriers were down already. I shook my head vigorously.

"It won't hurt. I am certain. You can go slow if you want and I have some lube with me." I tried to suppress my excitement while giving him an all lights are green sign but Bobby still wanted to continue this dance, probably enjoyed teasing me even further after I have begged him for so long. Bobby raised a mocking eyebrow.

"Why do you have lube with you?"

"Just in case." I whispered blushing slightly. Bobby lifted his arm and waved me to hand it over.

"Show me." He demanded with his words slightly slurred. Dutifully I let go of his bulge and turned over to my nightstand grabbing the tube and giving it to him. He turned onto his back and concentrated on the packaging reading it closely. I used the opportunity to quickly and as silently as possible wiggle out of my boxer briefs. Meanwhile Bobby had popped open the cap of the lube and I shot out my hand underneath it so he could place a glob of it on my fingertips. Bobby squeezed out some of the liquid cool gel onto my fingers.

"There you go brother." He slurred again playfully trying to sound more drunk than he was maybe to not take responsibility for what was about to happen. I was fine with that and shoved the cold gel up my butt crack spreading it around my twitching anus, briefly pushing my middle finger in to further lubricate all of my entrance. I slowly got on all fours next to him slightly wiggling my pale firm little ass in the air trying to not moan already. My own dick was hard already standing almost horizontal underneath me pushing up against my belly with every twitch from my excited asshole. Bobby lay on his side watching me, looking my naked body up and down ,seeing how ready and in heat I was. The pause went on a little too long and I started to wonder if my neediness would turn him off at the last moment.

"You can imagine your girl while doing it, no problem. What's her name again?" I whispered hoping that he wouldn't back off.

"Cassy." Bobby whispered. "Would you like to be Cassy for me?"

"Whatever makes you feel comfortable Bobby. You know you are my best friend and I really only want this to work for you. Bro's have to help each other out right? Life is hard enough as it is." Bobby got up on his knees and pulled down his boxer briefs letting his semihard cock jump out watching me wiggle and beg next to him. He stroked it once or twice pulling back his foreskin and making it fully hard, then he crawled up behind me and caressed my ass cheeks, spreading them a little, looking down at my wet glistening pink hole.

"You know I was thinking about breaking up with Cassy lately." Bobby said softly while he lifted his cockhead up and pushed it against my balls from behind. I was surprised at that statement since I thought Cassy was finally a girl who was willing to go further even without a proper engagement. At least Bobby told me that she had some slutty tendencies.

"Really?" I moaned out in surprise. "I thought everything was going well. I mean you call her every day and she seemed to be really into you."

"Yeah, she is. She even gave me a blowjob last time we went to the cinema." Bobby paused while slowly gliding his cockhead up and down my crack spreading lube around his red mushroom head. "But. But it didn't feel right, you know?" I gulped unable to think straight with Bobby's hard cock rubbing against my entrance.

"W-What do you mean?" I stuttered to keep him talking. Bobby let out a deep sigh and paused again in his movements.

"You know, what I need to tell you is – I was not able to cum into her mouth. Just couldn't do it. She really worked hard and wanted it but I couldn't. When she realized I wasn't going to shoot my load she comforted me and I told her it was because of my guilty conscious and then we never mentioned it, but it made me think."

"Well those things happen if you are excited or nervous. Don't worry." I tried to comfort him but Bobby stopped me mid-sentence.

"No. No. That is not it. You see I have no problem cumming in your mouth, Joe. Never. I can just relax and have a climax. What I am trying to say is that I think you are a better girlfriend than all the ones I had so far and I am not sure if I need anybody but you." A warm cozy feeling swept through my body as Bobby uttered these words and my knees went wobbly.

"Oh Bobby, I feel the same way." was all I managed to whisper overwhelmed with love and lust.

"I just fear that once I fucked you there is no way back for me" Bobby continued his cockhead still lingering between my ass-crack only millimeters away from giving me bliss.

"Oh please, please it will be OK. Don't overthink it. We are just best bro's. You will find a girl which makes you comfortable cumming in her mouth, I am certain. Maybe Cassy just isn't the one and this has nothing to do with me. I will be there for you no matter what. Let's just try it and see what happens." So close I couldn't bare it if Bobby now changed his mind. I closed my eyes and breathed deeply hoping that Bobby would stop thinking and start fucking. There was another long pause where Bobby let his hands glide all over my ass and my lower back caressing me like his little comforting pet.

"I guess you are right. But tell me once it hurts, yes? I will go slow" he finally uttered while grabbing my hip with one hand and aligning his hard cock with the other.

"Oh god please, yes!" I almost shouted out as I felt the pressure of his cock building up at my backdoor. I breathed out and tried to relax my sphincter. His cock was pretty huge, thicker than the things I tried to stick up my ass so far but it was also more flexible and therefore found its way in more easily. I could feel my elbows and knees trembling with excitement as the pressure built up and then subsided as Bobby slowly pushed against my anus and then pulled back a little. He was so gentle, so hesitating. I had a hard time to relax enough for him to not back out after a brief resistance from my backdoor. Showing him how much I liked it I started to moan and arch my back until he finally pushed hard enough to make his mushroom head slip past my lubed up sphincter and into my hot virgin asshole. I groaned deeply rolling my eyes back in my head and seeing stars sparkle before me. With the next gentle thrust I shoved my hips back further taking in more of Bobby's glorious thick veiny cock. For a brief moment I was in heaven but then suddenly I heard Bobby shriek up.

"Oh fuck!" He almost screamed between clenched teeth and jumped back off the bed leaving me all empty and longing with only a cold breeze against my lubed backdoor. I turned around looking what was going on and Bobby had already grabbed the bedsheet to cover his junk stumbling to the balcony door. We had our room on the ground floor so the balcony was level with the grassy grounds of the resort beyond. As my eyes followed Bobby's in the sudden confusion I could see two dark figures standing on our balcony one of which was holding a flashlight shining it into our room and tapping against the door.

"Oh my god!" I whispered going pale trying to find something to cover up but since Bobby took the bedsheets I only had the pillow to hold in front of my still hard dick. Bobby was also pale and shocked as I could see but since the knocking and the Arab voices outside didn't stop he managed to go over to the balcony door and open it a little. The door was shoved open and Bobby got pushed back into the room and two of the hotel security guards entered the room.