Timmy's Adv.-Dd Debbie

This is the third story in a short series about a shy college geek turned confident stud. It is a spin off from the "Kimmy's Adventures" series I've previously published. This story is an immediate continuation of Timmy's Adventures-Anchor Woman, that includes a flashback to another college sexual encounter. The initial setting is shortly after Timmy and Stacey, a TV news woman, and colleague, hook up for the first time.

This is a fictional story from the recesses of my perverted mind. Any resemblance to any real people or places is a coincidence. All characters depicted are 18-years of age or older.

Timmy's Adventures-DD Debbie

"So how'd you meet this Debbie Donahue girl?" Stacey asked, as she slid off me and got up from the bed. I got up and helped her pull the soaked bedding from the mattress.. "Wait, let me guess, you tutored her too?"

"How'd ya know?" I laughed as I used a dry part of the comforter to wipe Stacey's juices from my crotch and thighs. I began helping her stuff the wet bedding into the pillow cases.

"Deductive reasoning. You know I am a journalist," she giggled. "So tell me what's she look like? She's Irish right?"

"Yeah, Irish/Scotts ancestry from Kentucky," I answered as I began my story.

I saw Debbie, known by her friends as Dee Dee, for the first time on move in day my sophomore year. That was the same semester I met Kimmy. I was standing outside my suite holding a couple boxes, my parents were a few steps behind me, each toting a couple garbage bags with my clothes in them. Despite the commotion of students and parents in the corridor, I saw Dee Dee the moment she came out of her suite and gracefully headed down the hallway in my direction.

I was instantly awestruck by the petit, pale skinned beauty with a smattering of freckles. I remembered thinking I liked the fact she didn't over do the make up.

The fact that her tits bounced with each stride kinda caught my attention too.

Stacey let out a hearty laugh at my honesty.

The weather that day was very warm and as a result she was dressed in an outfit that showed off her, athletic body. She wore a tight, white, v-neck halter top that exhibited her large breasts, abundant cleavage and flat belly. She had on a pair of denim shorts that looked like they were painted on. Her feet were adorned with a pair of flip flops that showcased her pink toenails that I noticed were decorated the same color as her finger nails. Her long brown hair was tied back in a pony tail that fell to the middle of her back despite being tied tight at the top of her head.

I stood there gawking like a deer caught in the headlights until my mother's embarrassing words broke me from my trance. "She's a very pretty young lady, isn't she Timothy? You should say hello to her."

"Ha, ha, Ya gotta love mothers," Stacey said as she opened her closet and pulled out a clean set of sheets.

"Yeah, well I wasn't to happy with mine right then," i retorted.

At just that moment Dee Dee came to a stop at the Resident Assistant's (RA) suite one door down from mine. She turned her head in my direction, flashed a bright white smile and said "hello" before knocking on Gina, our RA's door. I guess she needed to ask her something. Anyway, I immediately felt all the blood rush to my face. I mumbled "hi" and quickly ducked into my suite. Luckily my parents didn't humiliate me more by starting a conversation with her.

Over the course of the first couple weeks of the fall semester I would see Dee Dee in the dorm and around campus, but I could barely look her in the eyes let alone think about starting a conversation with her.

As you can imagine Debbie got the attention of most of the guys on the floor, including that jerk Derrick. That first week of the semester I overheard Derrick's roommate say, "Hey you see the rack on that chick in suite 302?" Derrick goes, "Ya mean Double-D Debbie? Yeah I tried talkin' to her but she's a real bitch."

Derrick's reputation as an asshole preceded him from freshman year so I doubted his story. Well I would find out later that he tried asking her out. When she politely explained she had a long time boyfriend he was quoted as saying, " It's okay, I don't want some hillbilly's big titted ho anyway."

"Holy Fuck are you serious?" Stacey said in disbelief as we finished tucking the new top sheet into the mattress. "Why'd he call her a hillbilly ho?"

"She grew up in eastern Kentucky, ya' know, Appalachia," I answered.

"Anyway from what I heard, Dee Dee lit into him with a curse laden mountain talk tirade that tore him a new asshole. She was tough."

"I'm starting to like this girl a lot," Stacey said. "So how'd you end up tutoring her?"

"Actually it was more helping her with her homework and less tutoring," I said as I continued my story.

It was about a week after I started tutoring Kimmy. I was alone in the study lounge on my floor doing some work when Debbie came in. She gave me a sweet little wave and a cute smile and my heart began to race. I tried to remain calm and managed to squeak out a "hi".

She sat at a study cubby across the room from me and opened her text. From where I was sitting I couldn't really make out what it was, but it looked like some type of math. I went back to doing my work.

About ten-minutes later I hear, "Damn I don't get this shit!" then looked up to see Dee Dee slam her pencil down and drop her head in frustration.

Now you have to understand, in the past I would never have engaged in conversation with a girl let alone a beautiful woman like her. I don't know if it was new found confidence having tutored Kimmy a couple of times or what, but before I knew what I was doing I said, "Um what are you working on?"

Debbie turned around slowly and eyed me hopefully. "Statistics. Do you understand it?"

"Uh, well, I'm pretty good at math and sciences," I replied. "Maybe I can help?"

Before I knew it she'd jumped up from her seat and bounded quickly across the lounge towards the table I was sitting at, her books held tightly to her chest. She looked hot in her snug fitting grey yoga pants and loose fitting blue long sleeve tee-shirt. Despite the fact she was trying to downplay her well endowed chest, her breasts shook seductively as she took the seat next to me. I did my best not to stare, but began sweating anyway.

Over the course of the next half-hour I helped Dee Dee complete her homework and wrote down some hints to help her on similar problems. Upon completion of her work she asked if I'd be willing to help her again some time if she needed it. I willingly agreed and next thing I knew we arranged to meet twice a week.

As the semester went on I continued to help Dee Dee. Similar to the way I was starting to relax and get to know Kimmy while tutoring her, I became more confident working with Debbie. She was sweet. Sometimes she'd walk to class with me or we'd sit together in the dining hall.

It turned out she had a great self deprecating sense of humor. She would often joke about what she called the elephants in the room.

"I know Derrick and those other assholes call me Double-D Debbie," she told me one afternoon. "Shit, they think they invented that? Hell, when I was younger everyone used to call me Deb-Bra.

"But the joke's on those mother-fuckers," Dee Dee continued. "I haven't been a Double-D since middle school. These puppies are 38G's baby!" she said proudly, as she lifted them, then let them bounce to my amazement, causing me to blush.

"Thirty-eight G's!?" Stacey yelled in surprise. "And I thought my 34 D's were big?"

"Yeah and she's about five inches shorter than you," I answered. "Once she told me her bust size I estimated that her waist was about 28-inches and her hips around 34".

"Damn, big tits and skinny," Stacey blurted. "Fuckin' bitch! Stacey then switched gears. "Did that Derrick jerk see you working or hanging out with Debbie," Stacey asked just as we'd finished putting a clean comforter on the mattress and got into the bed.

"Hell the whole dorm saw us," I said grinning. "Little Dick was saying shit like, 'the only reason she was working with Twerpiliger is because he's gay.' Debbie heard that crap too. She was going to say something to him, but I told her to ignore it.

The more we were together we began sharing details about our families, friends and interests. I told Debbie about my parents, my childhood and passion for meteorology.

She explained that despite growing up poor, her teachers had helped her get into gymnastics, dancing and competitive cheerleading, since "before I grew these," she joked again, referring to her boobs. She said if it hadn't been her extra curricular activities she probably would have dropped out of school like many others in her town.

She told me about her boyfriend J.D. that she'd been dating since she was a sophomore and he was a senior in high school. She said he worked "now and again" helping at his Uncle's auto mechanic shop. Otherwise he hung out with his buddies drinking beer all the time. He wasn't real thrilled she wanted to go to college.

Debbie confided in me that she was afraid to go to college; that she wasn't smart enough to handle it. But, her mother's heart was set on her being the first in their family to get a degree. She wanted more for her daughter than getting knocked up and living on welfare. So her guidance counselor helped her get a partial scholarship for cheerleading as well as a work study grant and she got into State.

"You're right, that is a cool story," Stacey said, cuddling up with me. "Good for her."

The semester ended and she passed with a B. She was so excited she came down to my room to tell me and gave me a kiss on the lips, right in front of my suite mates. She turned and left with the guys all standing there with their mouth's open.

"What, ya never seen a nerd get a kiss from a hot girl before?" I asked, playing it cool. However, inside I was going nuts.

"Okay Don Juan, so when did the two of you do it," Stacey asked as she began fondling my flaccid cock.

It was the following semester. As a matter of fact it was exactly five days after my menage a trois with Pam and Rachel. Even though it was a new semester we continued to meet in the study lounge a couple times a week so I could help her with a general sciences class she was taking.

The moment Dee Dee walked into the lounge I could tell something wasn't right. Her eyes were all red and puffy and her usual radiant smile was missing.

"Everything okay, Dee Dee?" I asked concernedly.

"Yeah, everything's fine," Dee Dee lied. About five-seconds later she burst into tears, buried her face in her hands, and began sobbing loudly.

I sat in stunned silence for nearly a minute, uncertain what to say or do. Then I tentatively put a hand on her shoulder and rubbed it gently.

"I'm sorry you're upset," I finally said. "If you want to talk about it I'm willing to listen. Otherwise I'll just sit here with you as long as you want. Gradually Debbie lifted her head and gave me a little smile. "You know, you really are a sweet guy Timmy," she said as she wiped the tears from her face.

Another minute later she'd calmed down enough that she was able to tell me that she'd found out that her boyfriend J.D. was cheating on her with one of her friend's from high school. A mutual friend had called and told her.

My initial thought was, "good, you don't need that loser!" But I kept it to myself. Instead I said, "I appreciate your sharing that with me," I replied. " but I totally understand if you want to cancel studying for now and take time for yourself."

"I really don't want to be alone right now," Debbie replied. "Would you be willing to stay with me for awhile?"

"Sure," I said.

"Not here though," Debbie answered as she stood, picked up her books, then held out her hand to me.

Uncertain at first what to do, I tentatively stood, gathered my belongings and took her hand. She then led me out of the lounge and down the empty corridor towards her suite. I hoped she couldn't tell that my palms were getting sweaty. When we got to her door she unlocked it and led me into the common room. All of her suite mates were gone. She then had me follow her into her bedroom. Once inside, she turned and locked the door. We put our stuff on her desk then she guided me by the hand to her bed where we sat down next to each other.

As Debbie continued to hold my hand, she turned and looked into my eyes coyly. She leaned forward and her lips touched mine. I felt my pulse quicken and cock stiffen. Was this really happening? Was this beautiful woman actually kissing me? More than just platonically? Then I felt her tongue separate my lips and begin probing my mouth. Instinctively my tongue began tangling with hers. For what had to be about two minutes Debbie and I made out passionately until she finally removed her lips from mine.

'"Wow, you kiss really good!" Debbie complimented me.

At a loss for words I smiled proudly. My smile turned to disbelief as Debbie grabbed the bottom of my tee-shirt and began pulling it up my torso and over my head, then thew it on the floor.

"You've got more definition in your chest than I thought you would," Debbie said as she lightly ran her hand over my pecs. The idea that this gorgeous woman had thought about my chest was mind blowing.

Still silent, but suddenly emboldened by her comment, I reached for the hem of her V-neck,cable knit sweater and began to pull it up over her boobs. She helped me get it over her head and off her arms before I threw it on the floor next to my shirt.

I looked in awe as Debbie's white lacey undergarment barely contained her voluptuous tits. She smiled, then without a word reached nimbly behind her back, unclasped her bra and shrugged it off her shoulders allowing it to fall to the floor. There before my eyes was Debbie and her pair of the most alluring breasts, with large pink areola and long, stiff nipples.

"You're as beautiful as I imagined you would be," I responded.

"You've been thinking of me?" Debbie asked.

"Ever since the first day I saw you in the hallway," I replied.

"Well Timmy, if we're being totally honest with each other," Debbie began, "I've played with myself thinkin' about you once or twice."

I stared, at a loss for words.

Debbie smiled pleasantly then leaned forward and engaged me in another sloppy wet kiss. To my shock she began unbuckling my belt and unzipping my pants. As we continued to make out she tugged my jeans and boxers causing me to lift my hips which allowed her to push them over my knees and to my ankles. Finally our mouths separated and there we sat on the bed; her topless and me totally naked with a raging hard on sticking straight up.

With the grace of a cheerleader, Debbie dropped to her knees then swiftly removed my sneakers and socks before yanking my pants the rest of the way off my legs and throwing them across the room. She then positioned herself between my legs and grabbed my cock with her right hand. Slowly she began to stroke me causing pre-cum to bubble to the surface of the slit. She scooped a couple beads off the tip of my dick with her left index finger and looked at it, uncertain what to do. She gave me a quizzical look, then shrugged her shoulders and tentatively stuck her finger in her mouth.

"Ummmm, tastes sweet!" Debbie said. "Let's see how your whole cock tastes." Next thing I knew she devoured my dick to the base, dragged her tongue up the underside of my shaft then swabbed it over the nerve bundle causing me to involuntarily thrust my cock back down her throat. I hated the idea that she must have given head to her lousy boyfriend, but I couldn't help but enjoy what she was doing to me.

Surprisingly I didn't prematurely bust my nut. Debbie didn't miss a beat and bobbed her head forcefully six or seven more times on my dick before she came up for air. Somehow I still didn't blow my load. I wasn't the only who was amazed.

"Damn boy you got some staying power!" Debbie exclaimed. "I thought for sure you'd cum by now! That fuckin' boy friend of mine would have blown his load by now."

I smiled like a Cheshire Cat.

"When we first met last semester I thought for sure you were a virgin" Debbie stated while continuing to stroke my cock. "You were, weren't you?" I nodded the affirmative.

"But you're not a virgin anymore are you?"

I shook my head as I continued to smile broadly.

"Was it that girl who's friends with our RA Gina?...what's her name?...the cute flat chested runner... uhh...Kimmy?" Debbie asked.

"Uh huh!" I nodded. "How'd ya know?

"Well for starters I remember how she punked Little Dick Derrick when he was bustin' on you that first week of school," she began. "So I had a feeling she took a liking to ya. Then I saw the two of you working together in the library a couple times. On top of that I heard some rumors in the locker room about how's she's...how should I say it nicely...a bit fast, and I don't just me on the track."

I couldn't help but laugh hysterically as her sense of humor.

"So you two still doin' it or was it a one time thing?" Debbie asked curiously, still holding my cock.

"Just one unforgettable evening at her apartment around mid-terms," I explained proudly. "Well I guess twice if you want to count the blowjob she gave me in the women's bathroom at the library during finals week."

"Oh she is a little slut isn't she," Debbie laughed shaking her head. "So it turns out the two of us have had the same amount of sexual partners, who would have guessed our body counts would be the same? Turns out I been waisting my time all these years."

"Well, umm, I've actually slept with two other girls besides Kimmy," I admitted sheepishly. "At the same time."

"Are you fuckin' kiddin' me," Debbie exclaimed incredulously letting go of my dick. "Who? When?"

"Let's just say with two sorority sisters, at their party last Friday night."

"Wait a second!" Dee Dee exclaimed in disbelief. "You're not the 'geek' who kicked Derrick in the nuts at the Chi O house and was then seen going upstairs with two of the sorority sisters that I heard about, are you?"

"Damn word gets around this campus fast," I replied, smiling proudly. "That would be me!"

"I wish I'd been there to see it," Debbie answered. "Wish I'd been there t see you with those two girls too," she added grinning wickedly.

"Well I bet neither of those bitches were able to do this to you?" Debbie then exclaimed as she pushed me onto my back and suddenly took my cock back in her mouth. Before I knew it she lifted her head and enveloped my spit slick cock in her massive cleavage.

I groaned appreciatively as she quickly began to slide her juggs up and down my dick, while smiling seductively at me the whole time.

"Uhh...well...uhh...no, none of them titty...uhh... fucked me, that's...uhh...for sure!" I stuttered hardly able to believe what she was doing. To say it felt great would be an understatement. But the visual of my pink dick gliding in and out of her beautiful pale boobs was also very heady.

For several minutes she continued her assault on my dick with her massive mammaries while I watched in awe. Every so often she'd spit on the head of my cock to keep it slick as it popped out of the canyon between her tits. She varied her technique, sliding both boobs simultaneously for several strokes then rubbing them in opposite directions on my shaft for a few seconds. Every so often she'd pull my dick from it's warm cocoon and beat her nipples with it while looking into my eyes maniacally. Each act heightened my pleasure and I moaned and groaned in appreciation as my breathing increased.

The friction finally got to the point where I couldn't take any more and began to thrust my hips in sync with the down thrust of her tits.

"Debbie I'm gonna cum!" I exclaimed loudly.