Deidre Ch. 03

Timmy turned out to be an all right guy. Of course he lacked self-confidence, and always seemed to wear these awful brown-and-orange polo shirts, and jeans that were too big for him. Self-confidence has always been a big thing for me in evaluating a guy's worth besides a flashy car and lots of money.

Timmy had none of it, but his brother Jack did. I know this because: a. I saw him in person at the party and he was soooo HOT! And b. Timmy told me he had a great job and drove a Mercedes convertible. So... money and a hot car, plus ab's to die for, and who knew what else in those tight slacks he had on at the party.

But back to Timmy, who I promised to get laid; Elsie didn't want to cop his cherry, leaving it in my capable hands, so... I fucked his brains out in the backseat of his mother's BMW.

Along the way I learned that Timmy was strange, but in a nice way. First off, he had a decent sized dick, but not overly big. And, he kept it clean shaven, something that I hadn't come across in my limited knowledge of men and their firepower. But since we ladies shaved trimmed or depleted the hairs around our pussies, why shouldn't a guy do the same?

He also professed to wearing his mother's panties, preferring them to jockey's, but never to school as he had to shower after Phys-Ed classes, and the guys would have been unmerciful had they caught him wearing his mother's lingerie. In fact, I later learned of his penchant for cross-dressing, and even borrowed a gorgeous dress from him once.

Timmy was also a legitimate virgin. Oh, I had blown him the night before after he drove me home, but that doesn't count, I mean, ask the president.

I had him drive us to the park, found a secluded spot and we climbed into the back seat. We got naked. I extracted Timmy's smooth, hard dick from the black silk panties he was wearing, it was already drooling pre-come with eager anticipation. I started off by giving him a blowjob in which I experimented with some things I had thought of and some things that seemed to come naturally.

I rubbed my boobs up and down his shaft, and licked his tender, fat balls and slurped the purple head until he was harder than hard. When I took the head into my mouth I realized its texture reminded me of soft velvet, and wound up kissing it over and over again just because it felt so fucking smooth.

Timmy didn't know enough to tell me to get on with it, and so I continued my explorations, playing with the opening or meatus, as I came to learn a few years later. I teased the string-like portion coming down from the head to a ring of skin called the corona, using my lips and the tip of my tongue and gauged the silky smooth skin along his shaft, wishing my skin had a similar feel to it.

Timmy was almost afraid to touch me and lay quite still as I knelt on the floorboard (he had no mats in the damn car for some unknown reason and I was too dumb to ask why).

Finally I took him into my mouth, letting my lips slide over the head and down about three additional inches and noticed my jaw stretching a little to accommodate him. Then I let him out, well almost out, but not quite. But enough to inquire how I was doing.

"Um... just great... Deidre."

Gee, it was nice to know he remembered my name.

It was enough for me to take him back in my mouth and go to town, sucking on his pulsing penis, licking his balls and kissing my way up and down his shaft. I listened to each of his evermore pronounced moans as I slid my mouth up and down his dick. For kicks, I let my mouth fill with saliva, made a tight seal of my mouth and sucked while drawing him from my mouth, sort of like sucking on a peppermint stick when you were a kid.

"Wanna cum in my mouth, Timmy?"

"Maugh!" he answered. I took it as a yes and moved my head up and down from the head of his penis to about four inches beyond that, my limit at that time. I went faster, establishing a kind of rhythm with him that I know he appreciated.

Then I realized I was getting very excited and began moving my shoulders and back instead of my neck. It kept me from getting tired and probably provided me with more energy to finish him off in style.

"Cum for me baby," I whispered, looking into his frightened eyes. "Cum in my mouth."

Then I put his nice, red juicy crown in my mouth, pressed my tongue against the underside of the head, and jerked him off hard and fast until he came in my mouth with a little wail; gobs and gobs and gobs of hot, sticky, salty-sweet boy-come. I swallowed with gusto.

Afterward, Timmy surprised me by opening the glove compartment and filling a pipe with pot and getting the both of us stoned. A few minutes and a couple of wet kisses later I was jerking him back into fucking fitness.

"I know you're a virgin, Timmy, but I want to be your first woman."

I... I want you to be my first, Deidre," he replied quietly.

I ground my lower body against him, felt him grab my breasts and squeeze them, harder than I expected him to do, but still, it was gratifying as all get out to me.

"I've been waiting for this for so long," he said hoarsely."

"I want you in me, Timmy."

"I can't tell you how much this means to me," he said as his voice cracked with the emotion of the moment.

We fell back on seat as I opened my legs for him, and only then realized that I still had my jeans on.

"Wait! One sec, Timmy!" I grunted as I tugged my jeans down with an urgency I hadn't thought I had. I got my panties down to my knees before Timmy mounted me and I guided his cock into my pussy.

We tried it that way for a minute or so, but it wasn't working; he kept falling out on the backstroke. I had him get up and take my place on the car seat. Then I slowly sank down on his shaft with both of us groaning with sexual need. Timmy's eyes were riveted on his cock disappearing into my cooze while his hands ran up and down my thighs.

My pussy was tight yet slippery around him and I concentrated on holding him in me. (I was kegeling without knowing what the term even meant.)

Timmy had come once and I knew he'd last for a while, so I dipped a hand down to my pussy and strummed my clit while he squeezed my ass cheeks.

"Like it Timmy?"

"Oh yeah!"

"Play with my tits you want," I said huskily, making them swing back and forth in front of his face.

He seemed mesmerized for a moment, and then caught one with his left hand and brought it to his mouth and began sucking.

The thrill he caused went right to my clit and I had a little orgasm from it.

"How's that pussy, Timmy?" I asked after getting my breath back.

"W...wonderful!" He gasped.

"Wanna try another position?"

"Sure... I'm up for anything."

"You're up, that's for sure," I said and we both laughed.

After a few seconds, I leaned forward and kissed him then I dismounted and still on my knees, (not easy in the cramped backseat.) I leaned forward and presented my wriggling ass to Timmy.

He groaned at the sight then kissed each cheek in turn.

"That's nice, Timmy," I cooed, hoping he'd go down on me. But he was already rubbing his dick against me, trying to find my hole. I reached back, took him in hand and guided him back into my snatch.

He proved that he had some sense of manhood by taking hold of my hips and driving his dick deep inside me, and almost sending my face through the window of the car.

He was quick to apologize and I felt it was as much my fault as his and quickly assured him all was well and to get on with the fucking.

Gradually we established a rhythm, increasing our pace more quickly than I intended and causing my orgasm to come on even quicker. He never noticed a thing.

I knew he couldn't be far behind me and so I tried to work up another cum for myself, hoping we might arrive at one together.

We were pounding against one another for several minutes when I felt him swell up inside me. He's gonna cum, I told myself, and began to rub my clit feverishly to come with him as his hips smacked against my ass.

"OH!" he gasped and I felt his hot seed filling my pussy.

To his credit, Timmy kept on pumping and helped me reach another orgasm that was still in process when he pulled out and slumped to the floor of the car, completely spent.

We just held each other for a while, not talking, only catching our breath. When the silence was finally broken, it was by Timmy, who said: "I'd do anything for you, Deidre."

"You would?" I said, not believing my ears.

"Sure I would."

"So, would you tell your brother Jack about me?"

"What?"

"I said, would you tell your brother about me. I have kind of a crush on him."

And that's how I got a date with Jack Meadows.

*****

"So you copped my brother's cherry, did you?" Jack said after he parked his car in front of his seedy looking apartment. I was naïve and all, but I was still unimpressed with where he lived. After all, Timmy's house was really first class, but this... well, I was hot for Jack and went in anyway.

Elsie hadn't believed me when I told her he was taking me out and I had the secret thrill of knowing she was watching us as we drove off. Of course, I hadn't told her we were going straight to his place. I'd let her think I was being wined and dined before any hanky-panky. Anyway, I'd tell her the whole story the next day. It was too juicy not too.

Jack was twenty something; with a fancy car and the body of an ex-competitive swimmer not yet gone completely to seed. When I asked him what he did for a living, he said he was an investor, but neglected to say what he invested in. I was too busy taking in his good looks to think clearly, and when his hand slid under my dress I drifted away into a sexual haze that put my brain on hold.

I felt my pussy getting all gushy wet as his finger probed away at it. I didn't notice the wedding ring on his finger until he took his hand out from under the dress to lick his fingers.

"Are you still married, Jack?"

"Yeah, is that a problem?"

I said "No", and it really wasn't, and I didn't ask him any more questions.

He held the door to his apartment open for me, giving my ass a squeeze as I passed by and entered the apartment. It reminded me of my room. It was a mess of empty beer cans, food wrappers, clothing strewn everywhere, and an overflowing garbage can.

"Nice place," I tossed out just to say something.

"Yeah, thanks," Jack replied as if I was really complimenting his domestic skills. "So, how about it?" he said as if I knew what he was talking about.

"How about what?" I said.

"How about a blowjob. Timmy raved about the one you gave him."

"Oh... yeah... okay, where do you want it?"

"I'll sit in the chair, you can get on your knees, you know?"

He sat down and extracted his dick from his slacks. It wasn't intimidating at all. I mean, it was a nice size and all, but with his build and all, I had expected something close to Milton's enormous penis. So as I bent to the task I was kinda disappointed. He had one of those funky dicks where the crown is smaller than the actual shaft, which was pale, and strained up and out, curved like a drawn bow. A glistening drop of precum was balanced on the tip, like a dewdrop on a spear of asparagus. I stuck out my tongue and licked it off.

And was momentarily blinded by the flash of his camera.

"What the fuck?" I blurted in surprise.

"I take 'em for memories sake," Jack said by way of explanation.

I was eighteen. I didn't give a shit about him taking any pictures of me blowing him. I didn't think about the possibility that they might come back and haunt me some day, and so I blinked once or twice and got serious about sucking his dick, and running my hands over his magnificent body. I mean, his pecs and abs were to die for, at least I thought so at the time.

He seemed to be everything I had always dreamed of in a guy and here I was sucking him off.

Now Elsie and me love sucking dick. We hadn't sucked all that many at this point, but we had had a few, and thought we were world class at it. I started out just slurping the length, trailing my tongue along the underside of his rigid prick, kissing his balls and the petite scarlet crown; and then when he started to get really into it, I opened wide and swallowed.

I'll tell you up front, Timmy was longer and thicker, and along with Elsie, had practiced with a couple bananas to see if we could deep throat a guy. With Jack, I found I could get the whole thing in my mouth and keep it there, bobbing my head up and down and keeping my teeth well out of the way. I don't know about him, but I was more or less in heaven.

Jack was into it too, humping my face and calling me a horny bitch and a slutty little cunt. The more he talked, the hotter I got. His cock was swollen with excitement, trembling, practically pulsating. I could tell he was just about to come.

Right on cue, he yanked his slippery dick out of my mouth and started jerking off. It took about two seconds, and then he came, squirting his hot, sticky semen all over my face: into my eyes and hair, up my nose, across my cheeks and lips and chin. Again, the fucking camera flashed.

This time I managed to smile up at him as he clicked shot after shot of my cum-drenched face.

He gave me a washcloth to clean up then had me pose for his camera; shots of me on all fours, of my asshole, of my pussy, and of me holding my labia apart so "he could see the pink."

Finally he went to take a leak and I looked around the room. There was a picture of his wife, with clothes on, and one of a little girl, maybe three or four years old. The wife looked old and worn out in the picture, but I didn't think too much of it. Most of the women I knew in their thirties and forties looked that way, Mrs. Meadows being the exception.

I picked up Jack's camera as he strolled back into the room and flipped through the pictures he'd taken of me. The girl on the little LCD display looked pretty hot, I thought, mouth full of cock in one, cum splattered all over her face in another. I felt oddly smug looking at those pornographic snapshots. I wondered what his wife would say if she ever saw them.

Jack took the camera away from me then picked me up and carried me into the bedroom, which was cleaner than the living room. He later admitted he slept on the couch when his wife was at her mother's, leaving the bed fresh for her return.

"So why are we gonna fuck on it?" I asked dumbly.

"I'll give you clean sheets after; you can make it up again. She'll never know." "You better tell her you made it," I said, knowing my housekeeping skills were far from impressive.

I took off my dress and panties and hopped back onto the bed and waited with my legs spread, provocatively, I thought.

CLICK-FLASH another picture for his memory book. Jack stripped, and then attacked my nipples and pussy until I my pussy was drooling and soaking the sheets.

"Jack," I asked nervously, "would you go down on me?"

He did, but he wasn't an all-star at it. In fact, he was fairly clumsy and didn't seem to have any idea what he was supposed to do. His tongue was excruciatingly clumsy, seeming to lick everywhere except the neediest parts, and he was only down there for about two minutes before he came up for air, beaming like he had memorized the Rosetta Stone.

"How was that?" he asked, just as the doorbell rang.

He grabbed a robe, threw it on and trudged to the front door before I could muster a reply to his ineptitude.

I heard him talking to someone, and as horny as I was at the time, I started masturbating to keep everything nice and wet down there.

I suppose I should have flipped out when Jack walked back into the room with another guy in tow, but as horny as I was I took it all in stride, only putting a hand over my cooze to maintain a sense of decency.

He introduced the new guy as his friend, Dominic. Dominic looked to be about the same age as Jack, with a high forehead and hairy forearms and a bit of a belly and a greasy complexion. He smiled at me and said to Jack, not me, "She's got really nice tits."

Jack pulled a six-pack of beer from the refrigerator, and opened three and handed us each one.

Dominic set up a couple lines of cocaine, and I had my first taste of the white Lady. Mmmm.... The next thing I knew they were in bed with me, one on each side and I went to town sucking their cocaine-hard dicks, alternating between the two of them.

Dominic's cock wasn't much longer than Jack's, but it was notably thicker, and much hairier. I liked sucking Jack because it was easy to get the whole thing into my greedy mouth, and I didn't get his hairs stuck in my teeth, but I really enjoyed sucking them both. The situation was hugely exciting, and I savored the strong, male taste in my mouth.

Then Jack got up, rolled on a condom and started fucking me from behind, while I was still blowing Dominic.

I was really flying from the coke (I should add that we did a couple more lines prior to getting it on. I hardly noticed Dominic pulling his dick away from me and picking up the fucking camera. I did notice him when stood by the side of the bed and fed me his thick, strong-tasting cock again while shooting picture after picture of Jack hammering away at me.

Jack didn't last very long. He slipped straight into overdrive, humping wildly away at me, his cock twitching inside the condom as he came, emitting a series of stuttering grunts as he came. The guys traded places and Dominic maneuvered himself behind me and gave me a pretty good fucking while Jack snapped his pictures.

I was close to coming when Dominic yanked his dick out of me, peeled off the condom, and with a deep, drawn-out, guttural growl, exploded all over my back, splashing me with come from my butt-crack to my shoulder blades.

I collapsed onto the bed, a sweaty, panting mess. The two guys stood over me as I masturbated face down atop the sheets. They made small talk while I fingered myself, commenting on my body and snapping more pictures. I finally came, a long, deep orgasm that left me twitching, gasping into the bed linens.

Dominic gave me another beer and we did another line of coke, while Jack was making a phone call. I was pretty stoned when the next two guys arrived.

"Dee, meet Kevin and Tony," Dominic said as he opened another beer for himself.

"Man, look at that ass..." the one called Tony said as I looked around for something to cover my naked body.

Mmmm... fuckin' right, I'm gonna dig that...does she take it up the ass?" This was Kevin, the charming Kevin, as I still think of him.

I didn't hear or see the others arrive. All told there were nine guys in the apartment a few minutes later. They were all talking and I strained to turn my head far enough to see them, but because Tony was fucking me doggy-style and I had Kevin's thick cock in my mouth, I couldn't.

"All right, my turn," a short, bald-headed guy shouted. He had his dick out and was waving it around as if it were a club. It was big and uncircumcised and I watched as it grew even larger in his calloused hand.

"Lemme see what we got here, get the fuck outta the way, Tony!"

"Mmm...sweet meat!" he chuckled as his hand roamed from my flank to my pussy. "Goddamn, she's drippin' like a faucet!" he yelled out as his fingers rubbed my pussy.

He was obviously surprised at my condition. I don't know what he was drinking, I mean, I had already been worked over pretty well by the guys before he arrived.

I craved his dick. I could feel my pussy contracting on itself and juices were flowing and I couldn't hide it, especially when I felt the guys hand on me, his fingers sliding between my labia and pushing into my hot little cooze. Then I felt the head of his cock prick rubbing around the entrance to my pussy.

It didn't take long before he was pushing it inside, stretching me slowly and I really appreciated his taking his time. He was thick, not all that long, but girth counts for a lot and he had it. I could feel the tender walls of my cunt protesting a little as he shoved them aside, making room for the good hard fuck I was certain was coming.