Chapter 1 – Tiffany

My junior year in school, I was dating a guy on the baseball team named Ryan. He was a senior, just over 6 feet tall, played the outfield, had short wavy brown hair, and had a pretty cut body. He was a senior and would be graduating in a few months.

We had met at a mixer during the winter between my sorority and the baseball team. I took an immediate liking to him when he had begun flirting with me that night. He was flirty, charming, quick witted, and easily made me laugh. My kryptonite with men was then and still is men who can make me laugh. It’s had been and probably at all times will be the quickest way to my heart, or into my panties.

Our ordinary dates consisted of gonna fast food places, the local pizza shop, the bar on the weekends, and maybe a nightclub occasionally when I felt like dancing. I know nightclubs weren’t exactly Ryan’s scene, but he at all times humored me when I asked him if we could go to one. Probably because he knew I’d be wearing a tight dress and heels and would go down on him later after a few too many tequila shooters.

Well that, and to make sure no other guys hit on me. In school, I was about 5’6″, 130 pounds, had more than enough up top, and wavy blonde hair. I wasn’t the prettiest girl, but it didn’t take much to attract the attention of college guys I had found.

Our relationship was good, we got along well, had a vigorous sex life, and he treated me well. That said, I wasn’t naive, I knew full well we’d break up when he graduated. If not then, at some point over the summer, when distance would drive us apart. Which was okay, I’ve always been about the here and now, and for the meantime, our relationship was great.

Except for one thing, Ryan had an idea in his head about wanting to try anal. Looking back, I get it, every guy wants to mark their territory in as many places as possible. At the time I was apprehensive about it, worrying that it would be risky, messy, and degrading or humiliating.

It wasn’t so much the act itself that I found to be degrading or humiliating, but Ryan’s room at the baseball house and my room at the sorority house offered little privacy as people were always around and the walls at both places were paper thin. I didn’t need to be degraded by having a bunch of baseball players hearing my screams from getting screwed in the ass, before walking out past them. Similarly, I would be mortified by my sorority sisters hearing my getting screwed in the ass, only to hear their taunts for the rest of the semester about how I was an anal queen.

Still though, Ryan had indicated this was important to him, but did so in a way that didn’t pressure me to give into his advances. I found his approach to be tender, cute, and endearing. I couldn’t think of anything that was more of a turn off than when a man begged or outright pressured me into doing something. I was thankful that Ryan felt comfortable enough in our relationship to make his desires known to me without expecting that I do something that he wanted.

He was coming over that night so we could go out on a date. I was dressed casually in a floral purple top, faded jean shorts and sneakers. I had brushed my hair out and lightly applied a little bit of lip gloss and mascara.

Chapter 2 – Date Night

I saw him pull up in his beat up Honda Accord, and walked toward him with a wide smile on my face and a confident smirk on his face as he checked out my body. We had been dating for a few months at that point, and it still turned me on that he checked out my figure each time he saw me.

Opening the car door, I climbed in, sat down and leaned over to give him an open mouth kiss while rubbing his upper-thigh. He gladly accepted my advances. Had my hand been a few inches higher, I would have felt his dick twitch in his pants.

“Good to see you Tiffany,” Ryan said in his usual low raspy voice. “You’re looking lovely as at all times.”

I blushed at his compliment. He could always make me feel good about myself. Ryan looked good as well, in his tight black t-shirt and blue jeans. The shirt showed off the outline of his pecs and his biceps stretched the shirt. I loved wrapping my comparatively petite hands around his muscles as they flexed.

Driving to the pizza place, we held hands as I felt the warm spring breeze in my hair. On the ride, I thought about Ryan’s desires. He was always so good and kind to me, a wonderful lover, and college was supposed to be a time for experimenting. If we tried it and I didn’t like it, I was sure he wouldn’t bring it up again or stop if it was too bad.

Arriving at the pizza joint, Ryan escorted me into the restaurant, his arm around my back, his fingers stopping just short of my ass, which was a turn on. Ryan knew I liked his firm rough hands grasping my supple bottom, and even out here in public,

Walking into the restaurant, Ryan ordered for us, a large pizza with half pepperoni and half green peppers and mushrooms, plus a couple draft beers.

Sitting at the table, I sipped my beer and looked at him seductively in the eye from across the table. He made jokes about what happened during baseball practice that day, making me giggle.

After he finished his story, I looked him deeper in the eye and said in a sultry tone, “I want to try it Ryan.”

“Try what?” Ryan said. It was cute how he could be oblivious at times.

In a low voice, I said, “Anal.”

Ryan’s eyes bulged at me coming around to his request and blurted out in a loud voice, “What now!?!?” which caused several patrons to look at us.

Still in my low voice, I told him, “This weekend. Let’s make a production out of it. Get dressed up, have a nice dinner, and get a hotel room. A nice one. It will be a special experience for the both of us.”

Ryan nodded and readily agreed, happy for the opportunity to finally pierce my rosebud, “That sounds wonderful babe. It’s a date.”

The look on his face was one of eagerness and anticipation. I loved seeing that look in a man. It made me feel like I was the most important woman in the world. I reached across the booth, grabbed the collar of his shirt, and pulled him in toward me for another open mouth kiss. Usually I’m not one for public displays of affections, but I was so turned on at that moment that I needed him.

Our pizza came shortly after that. As we ate that evening I couldn’t take my eyes off of Ryan. I was going to jump his bones later that evening. I needed him so much at that moment.

After eating our pizza and having a couple of beers, Ryan escorted me back out to his car. I was leaning into him with my arm around him, not for the balance but for the comfort that his large warm body provided me.

Getting into his truck, I leaned over and whispered into his ear, “Drive us somewhere secluded, I need to feel you inside me at that moment.” Ryan’s eyes bulged once again at my forthrightness. While I always enjoyed sex, it wasn’t often I was this direct or outright slutty with him.

Ryan eagerly put the truck in drive and peeled out of the parking lot desperate for a secluded place, as I rubbed my manicured hand up and down the bulging muscles on his bicep.

I felt my vaginal canal get damp in anticipation of Ryan’s member entering it shortly. As he pulled down a dirt road, I moved my hand from his bicep toward his crotch, rubbing his member through his jeans. Ryan’s cock needed no encouragement from me, as it was already rock hard in his jeans.

I smiled at him. It was such a turn on that he was always so excited at the prospect of fucking me. I had been with guys in the past who had needed a little encouragement to get it up, but being with a man who got hard so easily delighted me.

Ryan stopped in a deserted area of the dirt road, put the car and park, and turned his attention to me. Caressing my cheek with one hand while pressing his lips into mine, he sneaked his hand up my shirt to massage my breasts.

I pressed back into him, kissing him for all I was worth, running my hands on his muscular torso. I was so turned on at that moment. To this day, I’m convinced that if we had lube that night, that Ryan would have fucked me in the back seat of his rusted out car that night instead of a warm inviting hotel bed a few evenings later.

Breaking the kiss, I breathlessly breathed out, “Let’s get in the back seat.”

Fucking in the front seat of the car was physically possible, but awkward. In the back seat of the car, Ryan could bend me over and enter me from behind. I usually preferred sex in the missionary position, but sometimes a desire came over me to be physically mounted by a man, and tonight was one of those nights.

Ryan nodded to my request. I climbed between the seats to get in the backseat of the car, while Ryan exited the car and re-entered in the back seat. We awkwardly but quickly worked to undress each other in the relatively tight confines of the back seat of the sedan.

Fully nude, I looked up at my masculine man and gave him a seductive smirk, and said, “I want you to take me from behind tonight babe. It will be a preview of sorts for our next date.”

Ryan smiled wryly at my wanton flirting and his dick twitched. Turning over, and lifting my ass in the air, while placing my face on the unvacuumed car seat, my horniness at the moment outweighed the unclean nature of the car.

I felt Ryan mount me from behind, grabbing my hips for balance and leverage as he brought the head of his dick to my slick opening, where he lingered. Ryan did this sometimes, when he sensed I was more turned on than usual, he wouldn’t enter me until I begged him. It always made me feel slutty, but even more turned on.

“Please fuck me Ryan!” I cried out. “I need you!”

Grasping my hips even tighter in a show of dominance, Ryan pushed into me, encountering barely any resistance, as I accepted every inch of him in one slow, but sure push.

I squealed out in pleasure. Pulling back out, he thrusted back into me again. And again. Before long he was clapping my cheeks as I was squealing in pleasure at my boyfriend’s assertive fucking of me. Fucking from behind sometimes hit just the right spot for me, and tonight was one of those nights and I quickly had an orgasm.

I was fortunate to cum so easily and quickly that evening, because Ryan was similarly turned on by my wanton attitude. Not even five minutes after we started fucking, he came with a loud grunt emptying, himself into me. While it would have been nice for the sex to last longer, I was satisfied and more than a little turned on that the normally long lasting Ryan had finished so quickly.

Ryan pulled out of me, and I turned over smiling seductively up at him, a fresh glow on my face from the orgasm he had given me. Looking up at him, I could tell he was relieved that I had cum as well.

Bringing my mouth to his cock, I eagerly licked up my cum mixed with his off his cock, looking him in the eye as I did it. I felt his dick twitch as I licked it at. When I had cleaned it, I winked at him, and gathered my clothes and exited the car.

Making my way behind a tree, I felt the urge to relieve myself from the beers I had drank. After finishing, I used the bottom of my t-shirt to dry myself before quickly redressing and returning to the car.

Returning to the car I found Ryan already dressed and seated in the car. Getting in I slid over and kissed him on the cheek. “That was wonderful, sweetie. Can you take me home now? I have an early morning tomorrow.”

Grinning back at me, he said, “Sure thing babe. You were great yourself.”

Driving home, I looked out the window into the night stars and hoped our date this weekend would go just as well.

Chapter 3 – Getting Ready for the Date

Over the next few days, I got myself ready for our date that weekend. Not wanting to discuss anal with any of my sorority sisters, I had gone to a local adult store to purchase lube and get lube, a butt plug, and a small dildo to practice with.

The woman working the register had pegged me as a first time forayer into the world of anal sex, and had offered me some friendly advice for my date with Ryan that weekend.

She told me to go slow, for Ryan to use his fingers to open me up, relax, listen to my body, communicate with Ryan, and to stop if it felt too painful. She recommended the doggy style position as that was the easiest for first timers. But most importantly she wished me luck and said to have fun with it.

Back at home, I was freshly showered and was going to dress to the nines for our date. I had just shaved and moisturized my legs, and they were positively glistening. Sitting at the vanity in black satin panties, and a black lace strapless bra, I applied my makeup. By the time I was done, my complexion was flawless, my eyes were smokey and seductive, and my dark red lipstick contrasted sharply with my white teeth.

Going to my closet, I pulled out a one-shoulder black floor-length evening gown. Pulling it over my head, I pulled it down over my curvy body, smoothing it out and noticing in the mirror on my closet door, how it hugged my curves. The long slit up the left side of my dress didn’t end until my upper thigh, exposing lots of legs.

Turning my attention to my hair, I used my curling iron to curl my naturally straight shoulder length blonde hair. Before long my face was cutely framed with classic curls. Silver hoop earrings and a silver chain necklace completed the look.

From my closet, I grabbed a pair of strappy open toed 5-inch heels. I didn’t often wear heels, especially ones this high, but I knew that Ryan was unlikely to forget this evening for the rest of his life, and I wanted to make it special for him.

Grabbing my black clutch purse, I packed it with the lube, my ID, keys, and my credit card. I also grabbed the evening bag for the next day that I had packed yesterday. Walking downstairs, I got a wolf whistle from my friend Amy.

“My, don’t we look fabulous tonight?” she teased. “Hot date tonight?”

“Ryan is taking me out to a nice dinner,” I told her in response. “Ryan said he wanted me to have a special evening.

“Well you do look wonderful,” Amy allowed. “I’m sure he’ll ravish you tonight,” she said with a wink.”

“You have no idea,” I said, with a similar wink back. “I have a feeling that tonight may be an evening we never get. But don’t wait up for me. I’ll be back tomorrow.”

“Well you have fun,” Amy said before making her way to the kitchen.

Chapter 4 – The Date

Ryan pulled up shortly thereafter, and I rushed out the door, walking as fast as I could in my 5 inch heels to his awaiting car with my purse and evening bag in my hand. From the look on Ryan’s face, I could tell he was smitten with my appearance. I didn’t dress up often, but when I did, I always hit the mark.

Climbing in the car, I brushed the long skirt of my dress under me and sat down, noting that Ryan had actually taken the time to vacuum out his car.

“Wow, you look incredible babe!” he exclaimed.

Blushing at Ryan’s exclamation, I blushed and said, “Thanks sweetie, you look good yourself.” Ryan was dressed in a button down black long sleeved shirt, tan dockers, and black dress shoes. He was clean shaven as well, which was a departure from the stubble that was typically prominently featured on his face. It made him look more handsome, but less rugged in my opinion.

Driving to the restaurant, my thoughts drifted off into the thought of the position that I would be in later that evening. I smiled thinking about how excited Ryan would be to explore a new sexual frontier for him.

“What are you thinking about Tiffany?” Ryan asked, catching me daydreaming.

Caught slightly off-guard, I smiled at him, and responded, “I was just thinking about how wonderful that this night promises to be.”

“I’ve been looking forward to it all week,” Ryan allowed, the eagerness in his voice clearly evident.

Ryan parked on the street outside the restaurant. He had chosen a quaint and romantic Italian restaurant in the cultural district of town. Walking around he opened the car door for me and offered me his hand to help me out of the car.

I was always more of an independent woman, but I smiled at his gentlemanly display toward me. It did feel good to be treated like a proper lady. Taking his hand, I warmly smiled at him and got out of the car. Walking the short distance to the restaurant, I felt closer to Ryan that evening than I had in a long time.

Walking in the restaurant, Ryan provided his name to the hostess for the reservation he had made. We were quickly escorted to a booth, where the hostess sat us. I always preferred the privacy of a booth over a table and unbeknownst to me, Ryan had specifically included a request for us to have a booth.

When the waiter came, Ryan ordered their most expensive bottle of Pinot Noir for us to share. He knew it was my favorite wine style, but I didn’t want him spending that much just for me.

In a low voice, I said, “Ryan, what are you doing? I wanted a nice evening, but you don’t need to purchase the most expensive wine to impress me. I’m sleeping with you regardless.”

“Nonsense,” Ryan said, waving off my concern. “We’ll enjoy a nice bottle of wine. Don’t worry about the cost, I got it covered.”

I appreciated his generosity, but I still felt awkward. And while I did like my wine, spending over $100 for a bottle of wine seemed a bit reckless at that point of my life.

Later in life, I would go on many first dates to fancy restaurants with men, and found that men would often try to impress me by ordering the most expensive wine or entree on the menu, rather than opening up and showing me their personality.

While I at all times appreciated their generosity, the men I at all times tended to gravitate toward and eventually date were the ones who had the confidence to take me to some local hole in the wall restaurant, where we’d have a couple glasses of house wine, or draft beer as appropriate with our dinner.

Back to the dinner, I looked at their menu and found the prices to be similarly expensive. This was less of a concern for me, as I wasn’t looking to eat a gigantic meal, given the position I expected to be in with Ryan later that evening.

Looking at the menu, I ordered the lasagna, as it was at all times one of my favorite Italian dishes, but it’s a pain to make by yourself, and you end up with a ton of it. Plus I knew I wouldn’t be eating all of my entree, and lasagna would reheat well in the microwave tomorrow. Ryan ordered the veal scallopini, which sounded delicious. I made a mental note to steal a taste of that off his tray during dinner.

As we waited for dinner, Ryan and I made conversation about our day. He had baseball practice earlier in the day, and had me in stitches laughing about his teammate who wasn’t paying attention and got hit in the groin with a baseball.

Was it juvenile to be laughing about some guy getting in the nuts? Obviously. Was it still funny though? Of course. Some things are at all times funny no matter how formal or professional the occasion is.

I told him how the current drama at the sorority house was that Tasha and Erin were at each other’s throats earlier that morning over some muscle bound meathead from the gym that they had both gone on dates with earlier this week and had to be physically separated.

It at all times amazed me how some women got mad at each other when the guy was obviously just sport-dating them. I had seen the guy at the gym, and he was as beautiful as he was muscle bound, but he gave off the aura that he fucked a different girl every week, just because he could. Guys like that would never be boyfriend material for anyone thinking with a clear head. It’s obvious Tasha and Erin weren’t.

By contrast, I was glad to have a steady boyfriend who was attractive, dependable, and clearly into me. Our food came shortly after that. I smiled at Ryan for the rest of our date as each bite of food and sip of wine brought me and Ryan closer to the expected high point of our evening. I was somewhat glad that Ryan had splurged on the expensive wine, it was excellent.