A Night (and Morning) to Remember

Journal Entry #34 - A Night (and Morning) to Remember

Hello Journal,

I had just started my second week of college and was sitting in the cafe when Tommy Jerome plopped his books down on my table and fell into the seat across from me. Tommy and I had a few rendezvous in the past, and he was a pretty good guy, but he had started hanging out with a different crowd during our senior year of high school and we hadn't seen each other much since then.

"Hey, Teri Girl," he said, pulling my stack of textbooks over in front of him and flipping through them. "What's up with you, girl?" He wore a long-sleeved gray shirt with a band logo on the front, grungy jeans, and skater-boy shoes. His hair was longer than I remembered, and the usually light brown, fine hair was greasy and dark.

I told him my class schedule and about a couple of my instructors, and then I asked him about his.

"It's cool," he said breezily, and then he leaned across the table and narrowed his eyes. "That's not what I meant, girl," he whispered. He sat back again and said, "I got something you might want to try."

Tommy had given me a few interviews in the past, so I thought he meant that he had done something outrageous he wanted me to include in my journals. He was handsome before, but now that he was kind of ratty and dirty, he had gained an amazing amount of "bad boy" appeal. I knew he was a player before, so I could only imagine what he had for me.

"What have you got?" I asked, pulling out my mobile journal.

"Put that away for later," he said, flipping it shut in front of me. "You ever gone anal?" he asked with a sly smile.

The idea was known to me, of course, the idea of it was at the same time frightening, disgusting, and hotter than hell. I told him I hadn't and asked if he had.

"Hells yeah!" he exclaimed. "It's the best! Teri Girl, I want to get into your ass!"

Not exactly the most subtle of people from the start, Tommy had come close to passing the limit and pissing me off. To talk about that openly, right there in the cafe! At school! The only reason I didn't slap him and ask him to leave was that the idea had made me so wet I couldn't stand it!

If you're familiar with the earlier encounters with Tommy you'll remember that I'm a fan of his dick. I've never seen anything like it. It starts out with a perfectly shaped head, but it's really small. His dick is like nine inches long, and from the tiny little head it gets thicker like a cone. When Tommy starts fucking you it's all gentle and stuff, but when things get hot and he starts going deep he stretches you good.

My legs were pressed together tightly under the table and I was almost trembling when I asked him, "When?"

"Tonight!" he laughed. "I'm living in the room over our garage now, so I get plenty of privacy. Come on over about nine and plan on staying a while."

"Do you want me to bring anything?" I asked softly.

"Just yourself, Teri Girl," he said, starting to get up. "Oh yeah! You know I like it when you wear those fuck-me shoes, right?" I said I did, and he walked away. I watched him all the way to the door, and just as he was exiting he shot me a smile and a wave. That smug son-of-a-bitch knew I was watching his cute little butt the entire time.

I tried to go back to my books, but my mind kept wandering to thoughts of taking Tommy up my butt, and my pussy was positively buzzing. After a little while I gave up and went home to get ready.

Mom is in Europe again, so I knew Daddy would welcome my news that I would be spending the night at Tammy's. Marcella made me some dinner and I went up and changed.

I know what Tommy likes, and I was dressing for him. I put on a short denim skirt and a crop-top T with no bra. I wore thong panties, with the waistband showing, and then put on bright red pumps with a six-inch heel. I don't wear them often, but when I do I usually don't spend much time on my feet anyway. I threw my cell in my little red handbag and double-checked my pill count, just to be safe.

I knew I was excited, because I arrived almost half an hour early. I parked down the block and stayed close to the tall shrubs that separated Tommy's driveway from his neighbor's. I got to the stairs up to his "apartment" and I looked at his house. As luck would have it I could clearly see his entire family, Tommy included, sitting around the table having dinner.

Tommy, his parents, and his two younger sisters were laughing and talking and having a really good time. I felt a little jealous of him for a minute before going up the stairs. I found to my relief that the door was unlocked.

I went in and turned on his TV, but I left the lights off. I sat on his sofa bed and watched TV for all of five minutes before my nervous energy got to me and I got up and started cleaning. I can't even begin to say why I did, since I don't even clean my own room, but I found myself putting his laundry in his hamper and straightening his stuff. If he didn't arrive when he did, ten minutes late, I probably would have vacuumed.

Tommy came in and closed his door, his eyes wandering all over me as he locked the door. "Hey, Teri Girl," he said softly, a hint of danger in his manner. "You ready to get rocked?"

"Ground rules," I said and watched as his face fell. He asked me what they were, and I told him. "First," I said, ticking off points on my fingers, "If I say stop, you stop. Second, you take it really easy on me. Third, we work our way up to it. And fourth, no booze or drugs."

"Not even pot?" he asked, looking at me like I had two heads.

"Only after, okay?" I asked, ready to drop it if he argued. He didn't, so that was cool.

He looked around his little apartment like it was a strange land and went over and sat on the sofa. The fold-away was hard to put away, so I knew he usually didn't. I sat next to him, leaning against him, with my legs tucked underneath me. My head was on his chest and we watched TV for a while. He smoked a couple of cigarettes, and then we started kissing.

I know I've never mentioned it, but I always like kissing Tommy, even after he smokes. His talent with his mouth is total, above and below. The only thing that saved him from getting a swelled head was that no girl had been stupid enough to tell him so.

His hands immediately climbed up under my shirt and he played with my titties while I rubbed his shoulders and back. I believe I got so into kissing him that all thoughts of our plans flew right out of my head. We made out for almost an hour, getting both of us really worked up. My pussy was throbbing and I knew his dick was too.

Tommy pulled my top off over my head and started sucking on my titties if anything making me wetter than I was before. He kept it up while I lay back on the sofa, and when I hooked a leg up over the back he got the hint and started kissing down my belly, not even pausing as he slid my panties off.

He sucked on my thighs as we worked my skirt up around my waist, and then he dove into my pussy, running his tongue around and into me, flickering on my clitty, and generally driving me mad.

I really appreciate a man who knows how to eat pussy and enjoys his work. Tommy definitely fits in that category. The one thing that I didn't appreciate was the stubble on his cheeks and chin. His face felt like a Brillo pad running across my most tender skin.

I could feel a righteous come building up inside me, and I bit down on the side of my hand when I realized that I was being so loud that his family and the neighbors probably had a pretty good idea about it too. His tongue drove deeply into my pussy and curled back slowly several times, leaving me shivering and shaking and covered with perspiration.

When his tongue dipped lower and teased across my perineum I squealed loudly before biting my hand again and I tightened up my tummy, but it wasn't enough to stop the rush and the next thing I knew the room had exploded with bright white stars and the sound of someone pounding out a fast-paced heartbeat on a big bass drum.

I was yowling into my hands when he pushed his finger into me. Quite unfair, that! I was already coming and he started fucking around inside me with his finger like that! I was riding the crest of my come as carefully as I could, and he was going to make me lose it and go under to be knocked around by the heavy surf. I had a moment of relief when he pulled his finger out and I started climbing back up the wave trying to regain control, and then he pushed his finger a little ways into my butt and I totally lost it.

I was kicking and whining for him to let up a bit, but he kept working on my pussy with his talented mouth and tongue, and working his finger in my butt in little circles, pulling gently, stretching me out a little at a time. A couple more stars exploded right behind my eyes, and then the big black star exploded and I passed out.

I became conscious slowly, wriggling in my sleep. I whined to let Tommy know I was back, but he didn't answer me. I could feel the deliciously dirty sensation of his finger sliding around in my butt, sometimes stabbing deep, probably up to the second knuckle, and when he pulled it slowly out I almost cried, because I was so scared I would crap on his sofa.

"It's better if you're on your stomach," Tommy said breathlessly, and he told me to lean on the arm of the sofa. His finger slipped out and I slowly rolled on to my belly and climbed up onto the arm. I was leaning on my elbows, on my knees, with my ass in the air. Tiny jolts of electricity were still shooting through my body, making my muscles twitch and jump, and my pussy was begging for dick.

I felt Tommy climb up behind me and felt his hard dick rubbing against my thighs and pussy when he leaned down and kissed my shoulder. He squirted something out of a tube into his hand and he rubbed it against my asshole. It wasn't cold or anything, but it felt a little like I didn't wipe well enough and that wasn't comfortable.

I felt the fat tip of his thumb press against my asshole, and I was surprised at how easily it slipped inside, stretching me apart and going in with a silent pop. I know I started making "ooh" sounds, and I felt a little pain when he would pull his thumb this way or that, stretching my little hole in slightly painful but strangely exciting ways.

I felt a sensation of pure ecstasy when Tommy slid his cock into my pussy. He slipped the tiny head in so easily and then slid it into me with a single long, firm thrust. The sensation of my pussy being stretched wider and wider was enough to drive me up the wall, but combined with his thumb action in my ass sent me wheeling head over heels into pure joy.

He started fucking my pussy with long, slow strokes, and I swear I almost heard my pussy say, "Thank you!" I stretched my arms out in front of me, hanging them over the edge of the sofa, and I started chewing on the upholstery, trying to muffle my loud moaning. Tommy kept up his long strokes, all the while stretching my ass with his thumb. Then he started popping his thumb in and out, and I felt the stars popping behind my eyes seconds before I went squealing into another hard come. Tommy, good man, started fucking me faster and harder, and I rode out my orgasm to completion, feeling like a million bucks when it ended.

Tommy pulled his dick out of my pussy and a second later his thumb popped out too. I tensed up, knowing what was going to happen next, and Tommy said, "Relax, Teri Girl! If you get tight it might hurt."

I relaxed as much as I could, and I looked back at him over my shoulder. He was rubbing his dick, stroking it slowly at the tip. I saw him move up close behind me again and felt his dick slip easily into my ass.

I started chewing on the sofa again, feeling the peculiar tickle of his dick in my ass and loving it, but still afraid that something might change and it would start to hurt. And then something did change. Tommy slid a little deeper, and my asshole stretched painfully around his thickening rod. I was about to scream, tears stinging my eyes, when he slipped out a little and my asshole grabbed onto the smaller head of his dick.

Tommy started to fuck my ass slowly, with shallow thrusts. It felt outrageously good, and by the groaning I heard it was pretty damn good for him too. Every few strokes he would go a little deeper, and I would whine and cry again, but then each time he would retreat and give me the good feelings again.

His hands were running over my back and sides, and every once in a while I looked back at him and saw the boy I knew, handsome and strong, a big happy smile on his face as he put his dick in me.

He slipped his hands across my ass and pressed his thumbs on either side of my asshole. He pulled my ass apart, I guess so he could see his dick sliding in and out better. At first it was kind of pleasant, but as he kept spreading it started to feel like he planned to rip me in half. I whined and tried to shake my hips, but even the inch or so of cock I had in me kept me still, afraid to tear something.

Tommy slid in again, going deeper and stretching me so painfully that I saw stars! I imagined (or maybe I didn't) I could feel something tearing, and I know I started to cry loudly and begged him to stop, but he didn't this time. Tommy kept sliding in more of his dick until I was lying motionless on the couch feeling like I had a two-liter bottle up my ass.

It hurt so badly I couldn't comprehend it really, but at the same time I could feel something very deep inside me going, "Oh yeah, baby, that's the stuff!" Tommy started to pull out, and as soon as I felt a wave of pleasure wash through me, the painful stretching having subsided, I was pressing back onto him, as though I didn't want the pain to stop!

I did! I mean, I really did want the pain to stop, and I don't know what got into me! I started slamming back against him when he pulled out of me, only relaxing when he fed his dick into my ass.

The sensation of having him filling me, stretching me, I've decided to call "Sweet Pain," because it hurts like hell, but like a really hard orgasm it's something I definitely want to feel.

Tommy was fucking me so nice and slow, and I was acting like a cock-hound, pushing back against him, and yelling at him to fuck me harder. Tommy let go of my ass and I felt another wave of relief, and then I felt his fingers dig into my hips. He was fucking my ass with firmer, faster strokes then, and I thank God that he didn't let loose and really bury his cock because I would have needed to go to the hospital.

Thinking back on it, I know I was yowling and howling and screeching like a cat in an alley, but I didn't care. My Tommy was giving me his dick, and I wanted all of it!

I heard his moaning getting higher in pitch, and when his breathing became ragged, along with the slowing of his strokes, I knew that Tommy was going to unload in my ass. I whined and begged him to come in my ass, still pushing back onto him, and when I felt the "whooshing" of his spurting come running up my butt I lost it again.

I came so damn hard that I was crying, tears running like twin rivers, screaming from the pain, jumping and twitching from pleasure, and begging him to keep it going! Sometime during my come Tommy pulled his dick out and sat back on the couch. I felt his hot juice running down and out of my asshole, but when I tried to tighten up to stop it I felt a blast of pain like I can't even describe! I wailed helplessly as his come flowed out of my wide asshole and dribbled over my pussy.

When the hardest part of my come subsided I tried to get up and bounce into the bathroom to clean up. Instead I put one foot on the floor, felt it give out, and tumbled onto the floor, hitting my shoulder on the table.

I was more embarrassed than hurt when Tommy helped me to stand up (not fully though, since my back didn't seem to work either). He walked me into the bathroom and sat me on the toilet before leaving.

I sat there, elbows on my knees and my face in my hands, and I cried for a long time, wondering if my asshole would ever close tight again as liquid kept dripping from inside me. When I tried to push it hurt, and when I tried not to push it hurt too.

I had a chance to laugh at myself, and then I took off my heels and put them on the counter. I pulled myself up to my feet and wiped carefully, feeling lots of pain when I pressed the paper tenderly to my ravaged ass and I cried again, almost panicking when I saw spots of blood on the tissue.

When I discovered it wasn't flowing, but rather was actually stopping, I made myself stand up straight. It is funny to write about it now (not that my ass is still very comfortable) but it was like my body was only working with a few parts at a time. When I got my legs to support me, my back kept me bent over, but when I straightened my back, my legs gave out.

I arranged a compromise and stumbled out of the bathroom and to the sofa, where I sat next to Tommy. His dick was hard and standing up proudly. I asked him how deep he went, and he smiled and looped his thumb and forefinger around his shaft about five inches down. Aroused, if not functional, I leaned over and took the head into my mouth, and promptly pulled away. I had to fight from puking from the taste of ass and lube.

Tommy laughed for a second, and I yelled at him. He got up and got me a beer, and then he went in the bathroom, leaving me to drink away the flavor. When he got back he took a pull from my beer and lit up. He offered me some, but I shook my head. Tommy grumbled and lit me a cigarette instead. He held me like that while we watched Nick at Nite, feeling our bodies get relaxed. By one o'clock I was ready for another try, but Tommy was pretty wasted so we cuddled up on the couch and fell asleep.

I woke up feeling a searing pain and realized Tommy was putting his thumb up my ass again. It's weird, I know, but at the same time I howled and punched his thigh, I felt my pussy get hot and wet, and my ass told me I wanted to go again. I climbed off of the sofa and got on my knees between his legs. I started sucking Tommy's dick just like the old days, and I loved every minute of it! Running my tongue around him, pressing against the fleshy underside of the head and making him moan, sucking it into my mouth and working him with my tongue and jaw. God I love to suck dick!

Tommy tapped my head, and when I looked up I saw he was holding something out for me. I pulled off and looked at the little tube he handed me. It was some kind of lube.

I squirted a big blob out onto my fingers and I wiped it all around and over his head, like I was building a tower of gel on him, and then I rubbed it in, stroking it down until he was thickly coated from the head to just past where I had taken him before. I got up and turned around, and I leaned back onto him, putting one foot up on the couch and leaning heavily on my arms, one on the arm of the sofa, one over the back. Tommy guided me down and I felt the gooey head of his dick press gently against my tortured asshole.

Now, everyone understands I was completely in control, right? No confusion? Okay, then please tell me why I immediately sat down on his dick until I screamed in pain, and then pushed up off the sofa, fucking my ass hard on his cock! I rode his pole like that until I couldn't go fast anymore, and I'm pretty sure I came at least once.

I was also sure the neighbors were going to call the cops because I was screaming bloody murder, but I was still in control. It hurt, but it was intense, "Sweet Pain," and I wanted more!

Finally I slowed down, and Tommy cupped my butt in his hands and helped to support me as we watched the sunrise lighten the windows. I was sliding slowly up and down his cock, and I could hear him gasping for air, a sure sign he is losing his fight to keep from blowing his load. I wiggled my ass (yeah, it hurt) and felt him coming up my ass immediately. After a few minutes I felt him starting to soften, and I kept up my motion until I was sitting on his lap, and his dick was soft beneath me, getting an ass-bath of his own come.