-Not suitable reading for people under 18 years old!- If you would like to send me feedback, send it to munanlutkuttaja@hotmail.com
INTRO
I have been dating now for 3 months, she is the first girl I have ever been with, she took my virginity and she has shown me so much. I used to be the sad, pathetic nerd of my school but ever since she came up to me and asked me out and started to date me, I have become the biggest rumour of the school. You see, I am not a jock, I am a small, blond, no muscle school nerd, I study hard, I dont really have many friends, other than other nerds of the school and I am totally inexperienced with girls, well I used to be. I turned 19 last month and believe it or not, my girlfriend is 27 years old, which is the cause of the rumours, why does a beautiful girl choose a person like me. I still cant believe how lucky I am, she came up to me, she was the one that took the initiative and still to this day she is the one who knows more about relationships so I listen to her and I take her advice. I would do anything for her, because she has done so much to me, and basically she made sex available to me, and boy, do we have sex alot! She likes it all, she takes it in the mouth, she likes me to go down on her, she likes anal sex and everything! And always she compliments me for it, calling me a stud and all I can do is devote my love to her. She also likes games and sometimes when we play cards, the one who wins gets to take the charge and I usually lose. The most fun experience she made me do once was to give her oral sex the whole time she was making food, I was licking her for more than an hour and boy, was eating food a hard job after that, my jaw had a hard time chewing or even moving but I enjoyed every moment of it.
It was three weeks ago when we decided to take a trip together, it was her idea, as most of these good ideas are. One evening when we were watching a movie together, and for the most time we had been cuddling she said that we should do something spontanius, I jumped up at that idea because at first I thought it was about sex and then it became alot better. She suggested that we take a trip together and I said something along the lines of a bus ride to the other side of the town and her response was calling me a silly boy and she said lets go to brazil. My jaw dropped and I was of course more than happy to go to brazil with her!
PART 1 The airport
I never have gotten over the fact that she is older than me, she cares for me, for who I am and that she is actually taller then me. It is every boys dream to meet a hot chick who knows how to please a man and is spontanius and likes to adventure... I had all that! I love her, I love Jessi! She was holding my hand and guiding me thru the crowds of people and I was following her lead, holding her hand and watching her golden hair move as we headed to the right place to board our plane. We stopped at the gate and she turned to face me, she kissed me and she said "See you on the other side." And with that, she turned on her heels and headed to the door that had the text "Staff only." She looked professional and I enjoyed every moment of watching her tight ass sway in her skirt as she walked thru the door. She had been working as a stewardess for 4 years now so this flight was practically free for us. I stood still for a moment infront of the gate to board the airplane, I imagine how much fun, how much sex we were going to have in Brazil and everything else. My last thouhgt before boarding the aircraft was "How perfect is my life!"
The airplane took off, and it had been an hour before I saw Jessi and we were half way to Brazil already. The food had been served and Jessica came to sit next to me, she said that she wanted to play cards, same rules as always, winner gets to make the decisions. I was blushing slightly as I thought that other people might be hearing us talk about sex games. The game was poker and for the first time in poker, the game ended a draw. I was suprised in this and I had already decided that if I win, I will get oral pleasure in the airplane toilet. I was snickering slightly as we decided to determine the winner by one draw, bigger card wins. I took my card first, it was a jack so I was feeling pretty confident. Jessica smiled at me and she drew her card and looked at it. She smirked devilishly and whispered in my ear "Follow me to the staff section of the plane and lets show our cards there to determine the winner, hm?" I nodded, already sporting a semi hard on with my 6" dick. I followed her to the back of the plane and a small set of stairs down to the staff compartment, it was a small space where they had all the coffee machines and food supplies but the most important thing was that we were in private and there was a door separating us from the rest of the plane. Jessi closed the door as soon as I had entered and she dared me to show my card first. I was very excited and I flipped the card from my pocket, proudly showing my jack. Jessi smiled and said "Uh-oh, looks like wittle Sam is at my mercy again." And with that, she flipped an ace to her forehead, bathing in her victory, giggling slightly. I knew I had lost and I did what I had been doing for a while now when I lost, wich was actually every time, I kneeled in front of her and said "I am at your service but next time, it will be my turn" I winked at her and she brushed my cheek with the back of her hand and smiled. "Okay, Sam, this time I have something very kinky in store for you." She went to a shelf and behind some boxes she took a plastic device and it looked frightening because it outlined the shape of a small penis. My first reaction was surprised and a little frightened but it soon turned out be just plain horny. She commanded me to lower my pants saying "I want you hornier than ever once we get to that hotel room, so I am going to make sure you are more than that. Now, I know you like anal play but this time we are going to turn the tables." I was puzzled as she produced a weird looking device, I had no idea what it was or what it was for but it looked remotely like an insertable device. Next to the plastic cage, this was starting to look very kinky, almost too much for me but she reassured me. "Now, this is going to stay between and there is nothing gay about this, it is just a game and I want to play with you, okay?" When she said the word gay, I became nervous and she could easily see that from me. She reassured me and asked me again to drop my pants, which I did. She kneeled in front of me and said "Trust me." Which I did, I closed my eyes, kept my hands to my sides as she pulled down my boxers and started to massage my cock which was painfully erect now. She rubbed my dick for a while before guiding it to her mouth and ever so slowly started to suck me. I tried to rock back and forth because I was yearning for release and she immediately stopped me with her hands so I stayed still. Her hands went to my butt cheeks as she was giving me slow oral pleasure and soon I felt her hands between my cheeks, I became worried but I enjoyed it, and her mouth felt even better because I was as nervous as I was when I was a virgin. Her hands touched my rosebud and I immediately tightened up, I didnt like where this was going but I trusted her and from previous experience, I trusted this was going to feel good in the end as it always had. Her hands left my butt and for a moment I tried to feel where they where as my eyes were closed and they returned to my butt as I feared. This time however, they were slick with some gooey stuff and her fingers were very slippery, they easily went between my butt cheeks without any friction. Again, my rosebud was touched and I tightened and immediately after, her finger slipped inside me! I gasped loudly and I was surprised that it didnt hurt one bit, there was only very intense pressure. As her finger was invading me, she started to suck my dick and I felt like my knees were going to give out. Her finger started to do this back and forth motion, every time pulling back as far as just outside my spincher and then back in which caused my dick to twitch every single time. My butt felt very slippery, her hand was coated with some form of lubricant. I felt like my dick was full of nothing but blood and sperm and I was ready to beg for release. Jessis finger left my butt and I felt relieved because to my surprise, it also eased my almost too strong feeling of cumming. I was confused how her finger had affected me so much and I didnt know what to think, I wanted to try it again but dared not to ask because she was in charge and it might seem gay if I did. Her head was doing wonders to my dick as her suction increased, her movements still were so painfully slow that there was no way that I would cum from it. Then, her finger touched my butt cheeks again. At least, I thought it was her finger but it wasnt, it was something slightly larger and round. I felt it tickle me as it passed my cheeks and rubbed against my lubricated cheeks until it met my spincher. I knew what jessica was doing and I decided to go thru with it, for her. I didnt know what it was that she was going to insert into me but as she again increased her suction and started to work her tongue violently on my dick now, I knew she wanted me to go thru with this. I moaned and I think she took it as a sign because the the intruder in between my butt cheeks started to press in. I moved my hips forward to escape the intruder and Jessi places her other hand onto my stomach to hold me still and the pressure was increasing in both my dick and my spincher. Soon, I felt defeated as the round object passed my spincher and it was shaped more narrow towards the length so it felt like my ass was eating this object more inside now and slowly it sinks in me until I feel it plop inside me and again as my spincher is without pressure my dick twitches violently. I leak a steady stream of pre cum into Jessis mouth and I am ever present with the intruder in my ass and it feels like it is going deeper in my ass, slowly but surely. Then, something else touches my butt cheeks, at first I hope it her hand but no, it is a round object like last time, this time slightly bigger. It too, makes it way to my spincher and I feel like crying, what is she doing to me?! Whatever it is, it feels good but also very embarrassing and humiliating, my dick is painful now, her tongue assaulting my purple head so badly. This new intruder also starts to push inside me and I know what follows, a wonderfully, yet embarrassing feeling of pleasure pulsing from my ass as the slightly larger object goes inside me. And it also is shaped more narrow along its length so it goes inside me as if my ass wants more inside me, this object is considerably longer and I feel it make contact with the first object, forcing it deeper. Both of the objects stop inside my bowels as I feel the shape at the entrance of my butt, there is a widening of sort that fits between my butt cheeks but does not fit inside my butt. There is actually a tear running down my cheek as it feels too good, something so wrong feels so weird and pleasurable. And then, my world come tumbling down as Jessis mouth leaves my dick and still, I feel intense pleasure, I am painfully aware where the pleasure is coming from. I open my eyes and I see Jessi now standing in front of me, immediately closing on me, kissing me VERY passionately, our tongues exchanging saliva and I part with her kissing, embarrassedly saying "Jessi, Im sorry, I dont really like this, it feels awkward." I was lying. Jessi smiled and said "Do it for me baby, and besides, look at your dick, I dont think it has ever been that big. Besides, Sam, there is nothing to be embarrassed about this, beacsue it you and me and no one else, okay?" I nodded slightly and I did admit it, althou not to her, it did feel good. Jessi smiled infront of me and planted a kiss to lips, I felt weird, I didnt dare to move because I knew what it would cause in my butt. Jessi looked at me and obviously was enjoying this. She lifted her hand and was holding a very small remote with two buttons, she said "Sam, in your butt, there is a small P-spot stimulator, I think it is called aneros prostate massager if I remember correctly, just enjoy it because many straight men do." With that she grinned wide and pressed the button on her remote. With that every single muscle in my ass spasmed as I felt an intense vibrating motion from the insides of my bowels. This time my knees actually did give out and I kneeled onto the floor and took support with my hand from Jennis leg. She was looking down on me and giggling slightly "Feels good, right!" I couldnt utter a word as I felt the vibration become more stronger as Jenni was rapidly pressing a button on the remote "Just wait Sam, its about to do something wonderful to you!" The pressure in my bowels felt like it was shifting, it was like, something was heading towards my penis and with every single pulse, which were probably many hundred in a second, a closing pressure was going thru my penis until I felt something let loose inside me. I was relieved that it was my bowels that let loose but it was an explosion of an orgasms, the feeling was intense, at first nothing came out of dick, just a wave of pleasure after another just like in a normal orgasm but it continued a lot longer! I was spasming involuntarily the whole time and Jenni was standing next to me, giggling the whole time. The pulsing continued and after a long time of having a dry orgasm my penis leaked its sperm but it didnt come out flying, it just poured out slowly. My eyes were tightly shut and as the intense orgasm started to fade out, I felt the intruders in my bowels become ever more present now, uncomfortable even. And when my orgasm was over, my penis starting to o flaccid, the things in my ass, felt wrong, painful and very uncomfortable. I reached with my hand to take them out but Jenni stopped me "Nono Sam, I am not done yet. Come one, I can guess that it feels very weird now but just hang tight Sam. Stand up." She offered me a hand and helped me to stand up, right after which she kneeled infront of me and cleaned my dick of any remains of sperm. The buzzing was still continuing in my ass and I was trying to get used to it because it was everything but nice. I was flushing red and I hoped that Jessi would allow me to remove what-ever-it-is that is in my ass. I felt Jessi pull something around my cock and I looked down to her curiously, trying to ignore the vibrator in my ass and see what was she doing, it was a plastic ring that she skillfully and without pain put around my dick and behind my balls. I was puzzled and then I remembered the plastic device, she must be putting that on me! Again, I was becoming slightly aroused and I felt myself become again so much more aware of the vibrator in my ass but the uncomfortable feeling fading away with every second and the embarrassingly and humiliating feeling coming back as it started to feel good. Jessi was working quickly as she could feel from my dick that I was becoming aroused again. She placed my dick inside the plastic mold and I realized with that moment that it was so small that I wouldnt be able to become erect. Jessi giggled again and placed a small lock onto the device and sealed it shut with it. My hands were trembling, the vibrator working inside me causing me to blush and sweat heavily and my cock unable to become erect, I felt violated, yet super horny. Jessi stood up in front of me and grinned "You should see the look on your face, Sam!" She giggled and then helped me to step out of my pants and boxers. I was puzzled and she produced a set of strings that looked heavier than my previous ones, I asked her what were they and she shushed me and said that I will see soon. She the boxers open and I stepped in to them one leg at a time and Jessi pulled them up. The boxers had a string inside them because as she pulled them to my waist, I felt them being very tight in front of me, forcing my cage penis into a small space and between my butt cheeks, I felt a sort of string sink between them and touch the vibrator's base. And these boxers, once in place, Jessi had pulled so up that they were above my hip bones and tightened them from the waist and locked them in place. I was mortified, I looked at her with a "What the hell are you doing?!" kind of look and Jessi smiled some more and his two sets of keys between her breasts. The boxers would be impossible to remove without cutting them open because they were so tight above my hip bones. She kisses me on the lips "Sam, this is my plan to keep you aroused thru the rest of the trip, to make it fair, I will give you a remote that will control the Aneros buzzing inside me right now so we can both control each other." She grinned and gave me an opportunity to speak. "Jessi, please, ease it with the vibrator, its killing me." I felt myself leak precum into my new cock cage and Jessi was smiling infront of me. "Alright, go down on me and make love to my pussy with your mouth for 20 minutes and I will consider making your state a little more comfortable but first admit it, it feels good, right?" I blushes and nodded sheepishly, admitting to her that it did in fact feel good in a sick way. I kneeled infront of her and submitted to licking her pussy for the next twenty minutes.
To be continued...