It all started with meeting Delialah. I was just sitting there in a diner around town, eating lunch and doing nothing spectacular. The afternoon wasn't looking to be anything memorable, I was probably just going to go home, jack off, and lounge around all evening. And then she came in, the first thing I noticed were her tits almost falling out of her shirt and her hard nipples as she walked through the door. I could feel myself growing hard as she walked towards me, as she approached my table, she smiled and leaned forward to rest against my table. “Hey cutie,” she said to me as her cleavage almost fell out of her shirt.
I am in no way a “cutie”. I'm about six foot three and slightly chubby, not the 'bad' kind, the kind that adds character. I am not athletic and I have to wear glasses that everyone says make me look like a professor. I blushed a little bit as she smiled playfully at me, her eyes shifting down from my now cleany shaven face to my growing bugle in my crotch. “Er... Hello.”
She giggled as she pushed into the booth with me, her ass pressing onto my lap. “I hope you don't mind me sitting here.” I was just finally getting over the shock of her amazing cleavage as I started to notice her very sexy ass. In the black shorts she was wearing it was still massive and in an amazing way. One of her cheeks was rubbing over my bulge which was growing, I was almost full length now and straining against my tight shorts.
“N.. Not at all.” I stammered as she continued to giggle over her shoulder at me. She was in no way tall and sitting on my lap, my head was still slightly over her shoulder. She shifted just a bit, letting her ass center over my cock, which was completely hard now. She put a hand behind her and rubbed my cheek as she started to grind up and down my cock. I finally let out a moan as she started to grind, she ran her other hand down her front and down underneath her. We sat there in silence except for me moaning for a few moments.
Finally, I felt something brush against my balls through my pants, I moaned a little louder and she spun around on my lap. Looking me in the eyes she softly kissed me and then whispered lightly in my ears 'I want you, but not here and not now. I have a few tests for you, to see if I should go all the way with you.' I stammered a little as she said this. 'Be at this address' she said as she wrote it down on a napkin and handed it to me 'at seven tonight, and be ready.' She smiled and winked at me as she got up and reached down as if grabbing for a purse, her lips kiss my cock head through my pants softly.
She got up and left and I gulped as I realized I had a massive erection and still had to pay my bill. I got up and in an odd stroke of confidence I let my raging hardon bulge out of my pants as I went to pay. The waitress and one blonde haired waiterboy (who really looked like a girl) grinned wide at me as I walked to the cashregister. The waiterboy even stopped short infront of me and bent over so my cock pressed hard against his asshole.
I was never one to fantisize about fucking a boy, but I was turned on and ground my cock a little against his asshole. He let out a moan as he stood back up straight, turning to brush a little more against my cock as he slipped something into my pocket. I paid my bill and left, hopping on my bike to ride home. By the time I made it home a lot of my horniness was gone. I reached into my pocket and next to the address was a little card from the boy.
I never had any reason to think I was bi before, or that I even had any interest in any cock other than my own. So there was a slight shock of thrill as I realized he had given me his number. I set the card down on my desk and I walked to my room to strip out of my clothing. Sitting down again at my desk in my boxers, I started my computer up. He left me a number, his name, an im name, and a website to look him up on.
I had to give him one thing. He was really cute. About five six, his bleached blond hair really stuck out in its outrageous hairdo. He was skinny, but not sickly skinny. He had just enough meat on him to make me get a little hard. And then there was his ass, oh god it felt awesome. I had had sex twice before and a few blowjobs, but I never rubbed a cock against someone elses ass. I'd seen it once or twice in a porno but I wasn't much into porn, so I didn't think anything of it. I set the card aside again and checked my computer. I looked down and saw that I was a little hard. But, I decided I'd mapquest the address. I was feeling the happy kind of sick, with nervousness, since I was unsure of what I'd do. By bike the mapquest said it'd be a about 20 minutes of a trip for me. It was only four, so I decided to sit and soak for a little in a bath. Nothing fancy, just some warm water and a chance to think about what that chick did to me.
As I went, completely naked to get dressed, I realized I had a thong from a bet I had made before. The details of the bet were vague in my memory, but me losing meant I had to wear a gstring thong to work for a month, and not the kind designed for guys, the kind designed for girls. The thought of wearing it out to the address today made me get a bit hard. I let out a loud moan as I walked to my draw and reached around for the leopard print gstring and discovered several other panties, thongs and lingerie. I guess each was a lost bet. I was trying to decide on which to wear, when a lacy pink girl thong fell on the floor and I couldn't help myself.
I let out another moan as it slid tightly up my legs and pushed my cock hard against my body and I felt the string ride up my ass. I felt pretty and gay, just like in that song. I rummaged through my draws. I found a skirt in my drawers, probably from my ex when she lived here, as I slipped on some skin tight shorts, I slipped the skirt in the pocket. I can't tell you why I was dressing like this or why I wanted to actual go out. But I put on a slightly loose black shirt and I went back to sit at my computer, the thong riding up my ass. I started to smile a little. I was feeling a bit turned on at this point and I added the cute little boy to my contacts list. He was online and had a streaming webcam. But I opted to not click it as I saw the time and that it was 6:30.
I went outside of my house which wasn't really a house so much as an overglorified appartment. I got on my bike. And let me tell you, a thong holding your cock in place while riding up your ass as you ride a bike is a bit painful but overall a really good and sexy feeling. The place she wanted me was an old apartment building in the center of town. It looked slightly worn out but it was still safe. The lights were on and I locked my bike next to it. As I went to walk in, I saw a bathroom. I don't know what compelled me to, but I walked in to change.
A pang of nervousness washed over me as I saw a few girls in there anda lack of urinals. I started to blush but the girls started to giggle. One eyed me up, I couldn't really see them to well and they walked into the same single person stall. One looked over her shoulder 'you can do whatever you want in here. You don't bother us in here. There's only one open stall though.' My cock instantly stiffened as I started to think about what she said. I stammered a little and walked into the open stall.
It was grimy and kind dirty but I was a guy and it didn't bother me. I started to pull my shorts down, as my thong becomes visible, I hear a whistle from the next stall, my cock growing hard and straining against the thong, now visible from the sides. I reach for the skirt and start to put it on. I hear another high pitched whistle. I noticed a large hole and an eye peeking through with a little writing over it 'Smile like a donut and get ready to suck.'
A girly voice came through the stall, the same voice as early. 'Mmm, sexy little boy, sit your ass down on that toilet.' I obeyed, not sure if it was part of the test she was putting me through or not. 'Good, now bend your pretty little mouth towards the other hole.' I turned to the other side of the stall and noticed another hole. Without questioning, I moved my mouth down to the hole. 'Good good, now get ready to suck. This is the first time you'll ever know what it's like to be a bitch girl.' The pink mushroom head of the cock popped through the hole first, I don't know if I was expecting the whole cock at once or what, but I let out a sigh at only seeing the massive pink head. 'Mmm, maybe little bitch boy wants the entire cock.' And then the remaining seven inches of the cock started to slide through the glory hole. 'Now, kiss it, lick the head, treat it like you made your girlfriends treat your own cock.'
Suddenly all my conviction was gone. I stared at the large cock for a minute and gulped. I heard snickering from the next stall over as the cock retreated out of the hole. I was sweating and I hung my head. I had just backed down when I had been so close to trying something new. The girls left the bathroom next to me, pushing my stall open, as I heard one of them comment “nice skirt, you look good in drag.”
I sat there on the toilet for a second, suddenly feeling I had to piss. I was now more nervous. Had I just failed a test? I wanted to throw up too. And then he walked by. The cute little gay boy from the diner. He smiled in at me as he walked by in a mini skirt and bra. He shook his cute little ass and walked towards my open stall. I paniced slightly, not knowing what to do. He put a finger to his lips and shh'd me. He walked up to me, shutting the bathroom stall door. 'Calm down.' before I knew what was going on, his legs were wrapping around my waist. His face was in mine and I noticed his pretty blue eyes staring at me. His lips suddenly locking with mine.
He was a great kisser, the making out was just blissful. I wasn't really aware of much else. All I know was a hand was moving up and down my body. The kiss was just amazing. And the kiss was over and he whispered in my ear 'hunny, poke me any harder with that cock of yours and you might burst through that sexy skirt and right into my ass.' I started to blush. He just smiled and kissed my cheek. 'I want to have a little fun with you before I let you go.' His hand was sliding down my chest, I shivered at the touch. 'Mmm, have you ever seen another boy's bare cock?' I started blushing and could only shake my head.
I started blushing harder as I realized my hands were both resting on his soft and yet firm ass. He started to grind over my cock just a little and I shivered and moaned again, his hand moving off my chest. 'Then it's hard time I showed you.' His hand was down at his zipper already, opening the black pants he was wearing. A cute pair of tyedye panties slipped out as he stood a little to let his pants roll down. 'Don't be shy, reach in there and touch it.' I hesitated a little and he just whispered reassuringly in my ear 'You had no problem probing my ass earlier.' I shuddered and found my confidence again. I rubbed my hand softly over those cute little panties. He whispered 'I can't wait to see what you're wearing under that skirt.' I shook a little in anticipation. My hand slipped into the tight waist band of the panties. I felt the head, soft and fleshy and so hot to my touch. He let out a moan. 'Pull it out pretty boy.'
My hand slipped the panties down, his half hard cock, longer then mine even part flacid, rolled out and tapped into my already hard cock through my pants. I reached down and started rubbing the uncut cock head. He moaned as I rubbed my hand over his cock. 'It's just like jerking off.' He gasped out between rubs. 'But there's a lot more you can do for me than I could do for myself.'
He stood up on something and stripped out of his cloths completely, his cock just inches from my mouth, my tongue rolled out of my mouth and licked the head as I shivered. He smiled down at me. 'Not yet. We have some warming up to do.' He dropped down off the toilet and opened the door, motioning for me to come out. 'Lose the shirt, keep the panties and skirt.' I took my shirt off and he motioned for me to follow him out of the bathroom.
I heard myself asking without realizing it, 'where are we going?'
He turned back to face me, looking amused. 'You'll see in a second.' I couldn't focus on his face as I was too busy at staring at his cock moving as he walked. He turned back around and all I could focus on now was that cute little boy ass of his. It looked tight and sexy and I felt my cock growing to full length again, I wanted to do nothing more than poke it and prod it into that butthole of his. I didn't notice much of where he was going. He shook his ass in front of me and I was out of its hypnotic effect. I was in a brightly lit and white tiled room. There was a sink of white marble and the toilet was just completely white. The bathtub was pretty large, big enough for two people and water. And those two people could probably do a lot. There was a few feet between everything and he smiled at me, telling me to sit on the toilet or the ground, it was my choice.
The toilet looked most inviting. I sat my ass down on it. IT was fairly cold and I shivered slightly. His eyes glimmered frantically, like he was trying to contain himself. 'Mmmm, now, for the warm up. Drop that sexy little skirt off.' Without hesitation I dropped them down. He grinned wide, his perfect white teeth even more attractive. 'Mmm, pink and lacy? So girly and sexy.' His hand rubbed them. 'Oooh, and a little string, my favorite.' His mouth seeming to water as he looked at my panties hungirly. He turned, his cock no longer facing me, but instead his pretty little ass in my face. He leaned forward onto the sink, his cheeks spreading. 'See that backdoor hole of mine?'
'Yes,' I said timidly.
'Good,' he reached behind and spread his asscheeks even more, revealing a sexy little pink butthole more. 'Now, lick it.' I guess I gasped or something cuz he said over his shoulder. 'You probed this little hole earlier.' I shivered and shook nervously and started to lean forward. I saw them then, little specks of brown. He spread the cheeks even more. 'Lick it all hunny. Don't worry, I'll return the favor soon enough.' I stuck my tongue out of my mouth and inched closer to the asshole. My tongue started to lick around and around, just grazing the brown specs, realizing they were bigger than I thought. I guess I gagged a little at first because I heard him whisper 'you get used to the taste.' And in no time I was licking everything brown specks and all, swallowing any of them large enough to be swallowed.
Suddenly, he stood up straight and pulled his ass forward. 'Now, more fun, close your eyes and open your mouth.' I did so without thinking. And then I tasted it again, the taste of a cock, his cock, the best I've ever tasted other than the brown specks. 'Keep those eyes closed.' The cock pumped faster and faster into my mouth, going fartheer and farther back. It hit far enough back to make me gag, my eyes opening as drool went around the cock and my eyes watered. 'Mmmm, guess the surprise is up.' He moaned as I was sucking his cock, his cock making me gag more and more each time. I could smell something as he fucked my mouth. 'Mmm, if you've never seen another boys cock, then you've never tasted cum have you?' I gagged something but he didn't hear. 'Oh silly me. Of course you haven't. Keep this cock in your mouth and drop your panties.' I just realized my hands were on his ass again and I dropped them down to remove my panties, my bare ass against the toilet seat, my cock popping out to full length.
'Good boy.' He was staring down at me, making eye contact with me, with those pretty blue eyes. 'Now keep sucking and tell me you didn't wipe well last time.' I gagged again. 'Hehe, silly me, you can't talk with me in your mouth. Just keep sucking.' He shook a little. 'I'm about to cum anyway.' The cock was in my mouth, I was in heaven, gagging and choking and all. And each second was glorious. And suddenly, my mouth filled with a hot white liquid. And I knew what cum tasted like. He sighed and pulled out of my mouth. 'Don't swallow yet.' He sat to stradle my waist. His cock touching mine. His lips pressed against mine, his tongue pressing into my mouth, swirling the cum. My one hand was on his waist, my other reaching for his cock to tease it. He swatted it away, breaking the kiss with half the cum in his mouth. 'Swallow it.' I did so as I kissed him again. He slowly lifted us both off the toilet seat, switching us around.
He sat down on the toilet breaking the kiss. He touched the head of my cock and it tensed up like I was about to cum. 'Mmm, you're ready to cum already sweetie.' I blushed, I had never been much of a preformer in bed. 'Don't worry, just turn around and lean forward on the sink.' As I leaned forward I felt his tongue swirling around my asshole, probing in, sweeping around, I heard him gag a little. 'Mmm, you didn't wipe.' His tongue resumed probing. I could feel my cock tensing. I moaned and tensed. 'Mmm, I'll stop this.' He got up and turned me around. I saw a full length mirror. I was staring naked with a cute boy naked and he was about to do something. He bent over in front of me. His asscheeks spread. 'You can choose where to cum now.'
I didn't think, I pressed my cocks head into his asshole and shoved in. I got a few inches of me in and then I felt resistance. 'Mmm. I love a nice hard cock up my ass.' I pressed in more, the resistance feeling slightly more intense. 'Hunny, sweetie, you press any harder and your cock will be mistaken for a blackmans.' I let out another moan as he pulled forward. 'Mmmm, lets see this beautiful piece.' He looked at my cock as I did too. I blushed as I saw a brown stain and small flecks over the head and shafted, but without hesitation his lips wrapped around my cock. Within seconds I was shaking and cum was shooting out of my cock into his mouth. He slowly rose as I finished cumming and kissed me, his mouth full of cum. He pushed it all in my mouth as he broke the kiss. 'Swallow it all.' And I did.
He smiled as Delialah walked into the room. Her voice, smooth and wonderful. 'This looks like the beginning of something wonderful.' I stammered and blushed a little. All I could manage was to stammer out if she saw all of it. 'Every ass licking and cock sucking second.' She reached over and stroked my cock a few times. 'And you're a lovely boy. You'll get to do me at some point. Now, you and Tom both look like you could use a shower.' She motioned to the shower. But that's another story.