Breaking Tiffany's Anal Cherry

Have you ever run into an old lover and wondered what would have happened if you had stayed together?

Tiffany Ann Thomas and I were an item in our junior years of college at "State". We were inseparable. Each of us had lost our virginity a couple years before, Tiffany to a high school boyfriend and me a year later in my freshman year at college.

She had been with three other guys and me two women before being set up as a blind date for Halloween in that junior year by her roommate Jessica. We met for the first time at the party, and I have to tell you it was quite different having a first date you couldn't actually "see".

Tiffany went to the party as Catwoman, with a flimsy black outfit that included a short see through skirt, stockings, skintight top and mask. I went dressed in a tuxedo and a Ronald Reagan mask, and I must say I looked presidential.

We were officially introduced at the party by Jessica, and spent the better part of the next two hours laughing, joking and getting to know each other. After the party I drove Tiffany home and received a very nice good night kiss and hug. She turned to head into the dorm then stopped, turned, lifted her mask and said good night again before slipping inside.

She was beautiful.

That night I fantasized about the girl and made a mess in my bed. The next morning I called her, asked her out again, and she accepted. That was the beginning of a relationship that lasted nearly a year.

On the night of our third date, we intensely made out and were both turned on to no end. Tiffany was stroking my cock through my pants and I was doing the same to her. When I asked her to take out my dick, she firmly said "no! I don't do that on a third date."

I pressed her for when I might get a little more, and she said, "Play your cards right and next time, who knows?"

We kissed for a little more, and then I thanked her for a great night.

"Huh?" said the girl.

"I was wondering if we could go out tomorrow morning?" I responded.

Tiffany looked at me strangely, but said sure.

I looked at my watch, which was passing midnight, then convinced her it was a new day and a new date.

That new date was incredible. We were still at the local necking spot, and the hourly visit by the local gendarmes had occurred. For the next half hour we made out before she unzipped my pants, pulling out a rock hard dick.

Tiffany stroked my cock for a few minutes, slowly at first then quickening her pace. All the while my hand was up her skirt fondling her warm moist panties. She wouldn't let me take off those flimsy panties but it didn't matter...I was feeling the moist hot pussy separated only by a little bit of cotton and I was in heaven.

I fingered her through her panties while she stroked my aching cock. I'd like to say I held off, but quite frankly it didn't take much for me to blast off. The toe-curling orgasm was fantastic and soon afterward Tiffany shuddered in an orgasm of her own.

It was a great fourth date, and for the next six months we were inseparable. The sex was incredible, as Tiffany was an adventurous lady. Because we both lived in dorm rooms, our rendezvous were often in unusual places. Oh, we did it in the car, and weather permitting at a local park, but we also found the janitor's closet, a "quite" room at the library and friend's attic were locations where we could grab a quickie.

Over time, though, we both realized it wasn't meant to be. We'd have little spats over dumb things, spats which turned into arguments and soon we were at wits end. The sex was great, but was happening less and less as we bickered over a wide assortment of things.

Right before the end of the school year Tiffany broke up with me, never to get back together again.

Flash forward five years. That's when I saw Tiffany shopping at Target. We laughed and joked about the old days before she startled me with the information that she would be getting married in two weeks.

It's funny, prior to that day I hadn't thought of Tiffany for years. Still, in talking to her that day I had a flashback to our relationship and, like a true guy, the sex.

I congratulated her of her pending marriage, we stopped for coffee, traded e-mails then went our separate ways. That night I pulled off to her, remembering those great make-out sessions, then fell off to a fitful sleep.

Work that week was a bear, and I didn't have a chance to think of much more than reports, spreadsheets and presentations. That Friday night I crashed early, watching television while eating take-out. Before heading to bed I decided to check my e-mails, when I noticed one from Tiffany.

"I'm at my bachelorette party and want to talk to you! Drop me a note when you get this."

I did, and minutes later I received a note with her cell phone number. I called, and Tiffany slurred a hello. She had just gotten back to her apartment and was totally sauced. She asked if I wanted to stop over, and minutes later I was cruising over to my former girlfriend's place.

I wasn't sure what I expected when I got there, but I have to say I was totally surprised. She opened the door and greeted me wearing a slinky black teddy. She handed me a beer, grabbed one for herself, then sat across from me. That gave me an outstanding view of her stocking clad legs, and, up her teddy, garters and flimsy panties.

Shocked, I asked her what was going on?

The girl looked at me, smiled, and then startled me. "I'm getting married in a week, and I have to tell you all the toys and lingerie and sexy games tonight at the party got me going...and somehow I thought of you. I was remembering those days in college, and thought, why not have one last fling."

With that Tiffany rose, walked toward me, and then fell to her knees. It wasn't long before she was sucking on my cock.

The woman licked the dick all over and then began an intense head session, bobbing her head like one of those little bobble-head dolls. I could not believe my luck, getting sucked off by a pretty woman who was spoken for. I nearly shot off but somehow held off, pulling her to her feet and kissing her pretty mouth.

We made out on the couch for several minutes before Tiffany spoke. "Fuck me," she begged, falling back onto the pillows and invitingly spreading her legs.

I slipped off her panties, slid between her legs, and slid into her hot wet pussy. We sort of held each other without moving before beginning a fuck that had us screwing all over her apartment. Oh, we started on the couch, but before the night was over we were linked together on the floor, in the shower, and in her bedroom.

The girl was unbelievable, and I could barely keep up with her. I have to tell you that bedroom was incredible, as I slipped into her from behind and banged her doggie style before slipping her around and cumming in her mouth. It was incredible.

But the most memorable thing she did happened after I fell asleep. I was in never-never land when I woke to something tickling my rear end. At first I thought it was Tiffany's finger, but soon I realized it was something moist...her mouth. The girl was rimming my ass.

"Oh my," was all I could say.

"Do mine," she replied.

I had never licked an ass, but on that night I learned it's a trait that's easy to pick up. I slipped under her, and licked her pussy before switching over to her nasty asshole. I licked up and down the crack, and then dipped my tongue into her anus. It was tangy, different, but the way she bounced around made me forget about how nasty it was and how hot the girl was getting.

"Fuck me," said the girl.

Again, I got behind her and started slipping my dick up and down her slit from the doggie position. Then she surprised me, reaching under to hold my dick and position it over her asshole. "That's where I want it," was all she said.

Pushing, I slowly entered her ass, first by an inch or so, and once she got used to it, and inch more and an inch more. Soon we were able to have a slow rhythm of me fucking her virgin asshole. There we were, two former lovers back together for a little serendipity, fucking like teenagers.

My dick loved the tight sensation of the young girl's ass. I held the sides of each ass cheek while I slowly fucked her butt. All the while Tiffany gasp and groaned a series of grunts as I banged her behind.

Reaching around, I began to finger her soaking pussy, and soon the girl was giving me all kinds of directions.

"That's it, that's it. Oh that feels so good. Fuck me harder. Fuck my pussy. Fuck my ass. Oooh."

Several orgasms shook the girl as I fucked her most intimate of spots. Her words and the motion of her ass soon milked out another cum from my well-worked cock. I shot my sticky sauce up her ass, banging it like it was a pussy.

Spent, the two of us feel into a fitful sleep. When the phone rang at 9 a.m., Tiffany could barely reach for it. "Damn my ass hurts, Rob, but it's a good hurt," she said.

Tiffany said hello then startled herself awake.

"Oh I overslept, honey, I need to take a shower....what? Uh, okay."

The girl hung up the phone. "It's my fiancé, he's going to be over in a half hour."

I jumped to my feet and grabbed my clothes as Tiffany threw stuff under the bed and attempted to make her house presentable. Our hearts raced as we tried to remove any traces of me. I dressed, then couldn't help myself. I unzipped my pants and pushed her to her knees. I jerked my cock a couple times, then inserted in into her mouth. I couldn't cum, but it was a great short blow job.

Looking at the clock, we said our goodbyes as she slipped into the shower and me out the back door. It wasn't until I was driving home that I realized she had cleaned off the cock that had recently been in her nasty ass.

I can only hope it might happen again.