Toby's First Time

I felt her cheeks. They were so big and firm and soft. The tip of my cock brushed past them and I knew I was about to explode, but did everything within my power not to. It was all happening so fast.

She looked back over her shoulder, "Are you ready baby? Ass only."

I nodded and rubbed the tip of my cock against the crinkled brown spot. It felt divine and she moaned. My cock is probably average in length but it is quite thick. I pressed the purple head which had never looked bigger against that brown hole, guiding it but it kept slipping on the lubricant.

Louise looked back over her shoulder and kept encouraging me, "Come on baby, bugger me, give my date a good poke."

She had her hand under her belly and I knew she was rubbing herself while I tried. Her words spurred me on and I pressed at that asshole with increased vigilance, watching as it protested against this unnatural invasion, it dimpled and widened at the same time. The tip went inside and her ring began gripping more securely. I kept pressing and her sphincter finally gave up and wrapped around the head as I plunged into her ass, head only. Louise gasped and arched her back. I pressed in further and she cried out.

"Easy baby, ease it in," she moaned. It felt incredible, so warm and tight it was almost unbearable and I began to climax on the spot.

"Ahh," I yelled and my cock slipped out and I came all over her ass.

Louise was moaning with me as I continued to blow the biggest wad of my life. I felt dizzy, my head spinning. Louise turned her head around and looked disappointed that it was already over with.

"Done already? You boys are hopeless," she said.

"I'm sorry," I muttered, still recovering then a dread set in, I'd blown it, literally.

I kept taking in deep breaths, she was still rubbing her hairy pussy, her soft pink lips opening and I could see how wet she was. My flaccid erection started to get hard again at the sight of her wet pussy and cum splattered ass. She reached around and dipped a finger in my thick white cum and brought it to her lips.

"Mmm, sweet," she said.

My dick was rock hard again, I didn't ask, I just began pressing my thick knob against that puckered and semen-coated asshole. She moaned and relaxed again, preparing for my penetration. I pressed with confidence and once again, her tight asshole slipped around my cock as she gasped and I slid my shaft halfway into her warm bowels. I pressed further and she arched her back suddenly and pressed me back so I went slower, bit by bit and finally, after it seemed an eternity I had my entire cock up her ass. Her sphincter gripped my cock obscenely, slippery with lube and she was moaning, urging me to fuck her up the ass. I held her hips tightly and pulled back and then plunged in the full way. She cried out every time.

"Oh god, I've forgotten how good it feels," she murmured, "fuck me in the ass Toby, yeah . . . "

Her words spurred me on and I thrust steadily into that beautiful backside for the next couple of minutes until I felt my jizz rebuilding. Her ass slapped against me as I came, filling her bowels with my warm semen. I held her hips tightly, until I was spent, she was cumming too, rubbing herself as I collapsed over her back, puffing with exertion.

We lay there for quite awhile. I can't remember how long, until I pulled my spent cock out, still reeling from the power of my orgasm and my first fuck. I'd lost my virginity to an ass, I wondered if it counted?

Louise turned around, her face flushed and we both got up. "I better drive you home now," she said, smoothing her hair.

She looked guilty and I just felt awkward, wondering if it were a dream. She lowered her nightdress over her cum splattered ass and we headed back to the backroom. I washed my spent cock which was rapidly becoming hard again watching Louise lift up her nightdress and wipe the cum off her ass with toilet paper. She tossed it in the toilet.

"I'll just get some shoes on," she said and headed off again.

My dick felt uncomfortable in my jeans, but I didn't say anything. I went in the kitchen and waited until she was ready. She came out some minutes later in her dressing gown and sneakers and drove me home.

"You won't tell anyone about this will you?" she asked after a time, "I mean not anyone, even if you think they won't tell anyone. I shouldn't have done it, but I've been so horny lately."

"Of course I won't tell anyone," I said, my mind reeling. Was I going to do it again? It didn't seem likely and I felt depressed and horny at the same time.

"Why doesn't your husband um . . . do you that way?" I stammered.

Louise looked at me then back to the road, "Oh I don't know, he thinks it's dirty to stick his dick up a girl's bum. My boyfriend before I met him wanted to do it and I thought it would be a dirty thing until he talked me into it, From then on he stuck it up my ass every time we had sex and I never came more intensely."

My dick was rock hard thinking of getting that kind of action every night. We pulled up at my house and I was not sure what to say. "Can we do it again some time?" I inquired, trying to not sound desperate.

She smiled, "Did you like it Toby?"

"It was awesome, Louise," I said. My dick was so hard it hurt.

She sighed, "I don't think so, I shouldn't have done it in the first place, lust got the better of me. I think it would be better if we just forgot about it, pretend it never happened."

Her words crushed me, but she was probably right. I didn't want to ruin her family.

She looked concerned, "Are you okay Toby?"

"I guess," I said, then added, "I just won't be able to stop thinking about you."

I looked into her eyes and she smiled and noticed my bulging jeans, "I can see."

I stared at her and then leaned over and kissed her on the mouth. She stiffened and then allowed me to kiss her. It was just lips to lips, but she relaxed after a moment and let me slip my tongue into her mouth. Our tongues met and she was a great kisser. We made out for a couple of minutes and I squeezed her large boobs, getting a healthy moan in response. Finally she broke away, breathing heavily.

"Stop it," she said, "You're only making it harder."

"I know," I said, indicating my crotch. She laughed and gave me one last peck. "Go on get home."

"You can't leave me like this," I protested, feeling bold, "I'm not going anywhere."

"Toby," she said, assuming a motherly voice, "Go home this instant!"

"No," I said, figuring I had nothing to lose. To add to it I opened my belt and took out my throbbing erection, which stuck straight up in the air, thick and ready for anything.

"Toby," she trailed off, her eyes drawn to it. I took her hand and guided it to my cock. She resisted slightly but took it in her firm grip and started giving me a hand job. I moaned as she wanked me.

"You're a really bad boy," she moaned as she stroked me. I could tell she was really turned on now.

"Do you want me in your ass again?" I asked.

She moaned at the question and I knew I found her weak spot. She kept wanking me and then to my surprise she leaned over, peeled back my foreskin and wrapped her lips around my cock and began sucking me. I gasped at the sensation. With one hand she massaged my balls while she went to work, moaning as she sucked my cock, her tongue swirling expertly around the head. I gripped the door handle. The sensation was incredible. She sucked slow and deep, then stopped for a moment to lick my balls, taking one in the mouth and then the other. I was in heaven.

"Oh Jesus you're awesome," I gasped.

Her mouth full of cock she murmured something. I looked over at her bum that was raised slightly off the seat and reached my hand over to squeeze and fondle it. She moaned in response. I pulled the nightie up so her bum was bare and squeezed her generous cheeks and then found my way to her puckered brown rim. It was still lubricated from before and I stuck my middle finger in her ass and began fucking her with my finger.

She cried out at the intrusion and began sucking more vigorously. I responded by sticking my index finger with it and began fucking her ass hard with my fingers. Her mouth came off my cock as she yelled in ecstasy as I finger fucked her ass over the next few minutes to an intense orgasm. She panted, shook and yelled my name until her orgasm subsided. She resumed work on my cock with renewed enthusiasm, sucking me hard until I exploded in her mouth, my third intense orgasm of the night.

She didn't remove her mouth, just took every burst until I was spent, swallowing as much as she could. She kept sucking me until I was limp again and then raised her head, her face flushed. She had cum over her lips and down her chin. She was breathing heavily. She wiped the cum off her face, licking up the drops and calming herself. She pulled her nightdress back over her naked buttocks.

"You a very naughty young man," she said.

I leaned over and kissed her again and she let me, putting her arms around my neck as we kissed passionately. I squeezed her tits and bum and made my way up her inner thighs. She pulled away.

"Go home Toby," she said, "I mean it this time."

Disappointed I decided to do what she said, "You're incredible," I said lamely, then added firmly, "I will see you again Louise."

"Maybe," she smiled mysteriously, "but don't get your hopes up young man."

I got out of the car and blew a kiss to her. She looked at me and laughed, "Do your fly up."

"Shit," I muttered and zipped up. There was no one around at this time of night. In our passion we hadn't even checked the street. Anyone could have been watching.

"Bye," she said.

"See you soon," I said hopefully and closed the door.

She drove away and already I begun to feel empty without her. I wished I could have slept in her bed, together like lovers, but it didn't happen. I tried to look at the bright side that it was better than nothing and it certainly was. But it just left me wanting more of her. I just hoped that one day, I would get the opportunity again.