Should Have Been The Bad Boy

When I went back to school for my Master's, I worked at a bank near the university. It was a great job because girls would come in needing help with their accounts.

One girl I remember in particular, Alicia, was just crazy hot! She sat down at my desk and we talked quite a bit while I was helping her out. She was all giggly and flirty, and I was surprised because even though I'm pretty good looking, I normally would have thought that this girl was out of my league.

She was blonde and VERY tan, and her enormous tits were just barely being held in by a cute little baby tee. Before she came over to my desk, I had seen her leaning over the counter at the teller window, and her tight little skirt was only a couple inches long enough to cover her more than sumptuous ass.

After talking a while, she told me that she worked at one of the local resort-hotels. I told her that my friend Joyce worked there too, and asked if she knew her. She said yeah and that Joyce was awesome, and that I should have Joyce bring me around to one of their parties. She left with a smile, that was super-sweet and devilishly mischievious all at the same time. I still think about that smile...

So Joyce calls me later, and tells me that her friend from work, Alicia, has been asking about me and wants to go out. She told Joyce to give me her phone number. This is awesome because had I called Joyce first I would have been asking all about Alicia, too.

So I call her up, and we plan out our first date for that weekend. We go to dinner in the downtown area of our college town, and she is dressed to kill. A light blue spaghetti strapped top, and skin tight black pants. We had a great dinner and great conversation, talked about a lot of things we had in common, and after drinks, headed to her house. We did a little making out that first night, and I loved the feel of her soft tongue in my mouth.

The next day, we wanted to see each other again, but she had to pack for a cruise she was going on with her mom and sister. She asked if I wanted to come over and watch a movie. I said of course, and that I'd bring the wine.

I got there and she invited me right to her room. She went to make popcorn, I opened the wine, and we started watching the movie, stretched out on her bed. We stopped paying attention to the movie relatively quickly, and started where we had left off the previous night, passionately kissing.

She was laying on her back, propped up on her elbows. While our faces were close, our bodies were pointed in different directions. Her breasts were right in line with the left side of my body, and I began to massage them with my left hand as we kissed. With her back to my chest, my left hand was all I would have available for awhile. My fingertips began to trace across her stomach, and along the waistline of her low cut sweatpants out to her rounded hips. I was doing all of this touching in a very teasing way, and I could tell it was getting her very excited. Her breathing was heavy, her heartbeat was fast, and sexy little whimpers and sighs emitted from mouth while our kisses got deeper, stronger, harder. I loved those kind of kisses from her, there was real aggression behind them, intensity I could see when she'd back away for a moment with that devilish grin.

I slid my left hand down the front of her sweatpants and under her tight panties. I felt her neatly trimmed area on the way down to her soft, wet lips. I thought I'd work on getting her pants down, and attempted to untie her drawstring with the only hand that I had available to use. I pulled and nothing happened, I could tell I had knotted them up pretty good, and it was obvious that those wouldn't be coming off without some help. I went back to touching her. I teased her most sensitive area, lightly running my fingers all along the length of her slit, and dragging softly near her clit. She wanted her pants off too, and when she tried to slip them off her hips, she laughed and asked what I had done. I told her I had no idea, and laughed a little too. She got up to work on taking them off, and it even after she turned the lights on, it wasn't easy. She gave up on trying to undo the knot and instead wiggled them off going over one hip at a time. She went to turn off the lights, and as she turned I caught my first glimpse of her fantastic ass in her thong underwear.

As she came back to bed she lifted her t-shirt over her head and removed it. I did the same with mine. She laid back down beside me, and this time, she was faced the other way, and I could reach for her with my right hand. I slid my hand underneath her panties once again and started to penetrate her with my middle finger, shallow at first, then deeper and deeper. I could feel she wanted more, and quickly slipped a second finger inside her. I tickled the front wall of her vagina with those two fingers, and could tell that her g-spot was being reached, as the sounds coming from her were getting louder, and more gutteral. She lifted her hips, and began to shift them with the rythym of my insertions. She grunted loudly as she was overcome by the power of her orgasm. I was able to feel the contractions of her vaginal walls all around my fingers, and even after her body collapsed down back onto the bed, and I could feel gentle pulses inside her. Her breathing was broken apart, her body was trembling and she had worked herself into quite a sweat. She was moist to the touch, and as I kissed her neck, I tasted her sweet skin and her salty perspiration.

As we lied there together, she thanked me for how I made her feel and told me that she believed in reciprocation. She got off the bed, and with her back to me, removed her bra. She got onto her knees, and I moved to the edge of the bed. She reached for my belt, and began to remove it. My penis, began to engorge with blood, and it would be hard well before she got to removing it from my pants. She slid my pants off and tossed them on the floor. She reached into my boxer briefs, and emerged with my cock in her hand's firm grip. There is something so exciting about that moment where my dick is released and exposed to a partner for the first time, even better when she has gone in to take it out herself.

She began to stroke the shaft slowly, and it felt unbelievable. Part of what we had talked about the night before, on our first date, was how she was taking classes to become a licensed massage therapist. We had held our hands palm-to-palm, and I was shocked to see that her hands were only slightly smaller than my own. And now, she was alternating those hands in servicing my swollen cock, and I could tell that those hands were strong, too.

Even though she was working on me dry, her firm grip ensured that the handjob was pleasurable. That didn't matter for long, however, because no sooner than this slight concern had passed through my mind, I felt the tip of her tongue dancing around my head with gentle, quick licks. She then flattened out her tongue, and starting at the base worked slowly all the way up the length of my member. Then I saw a flash of that devilish smile again, just before the tip of my penis disappeared into that beautiful mouth. She worked up and down as I laid back and enjoyed. I couldn't prevent words like "Holy Fuck" from exiting my lips. She would stop sucking for a while and continue to work me over with her hands, and since I was lubricated with her saliva, she could lessen her grip, and allow me to slip and slide in her hands more. Then she'd firm up the grip again placing her mouth over my head, and stroking me with her hand and mouth in unison.

Everything was feeling amazing, and eventually I would have erupted with a massive load, perhaps into her mouth or all over her ample tits. She was only 20 however, and unfortunately I don't think she was used to guys lasting this long when confronted with her warm mouth and her very skilled hands. She asked me what was wrong and even though I said "Nothing", she thought that I wasn't relaxed enough, and said, "I've got something to help you relax." She stood up and eased the thong off of her hips and let it fall to the floor. She climbed on top of me, reached behind her grabbing my penis, and eased it into her eager, wet slit. I held her against me, sucking on her nipple as she began to ride. We kissed, and my mind was spinning. This felt great, but I wasn't wearing a condom. I also had concerns that we might be rushing things. We had gotten off to a great start, and I was thinking more along the lines of having a real relationship with this girl. I had been in other relationships where getting into sex too soon had contributed to the failure of the relationship.

She got off my lap, and we talked about how we felt and I spent the night sleeping next to her. I felt bad for not giving her the sex that she had initiated, so I didn't do anything more than kiss her for the rest of the night. I was tempted to eat her juicy pussy, but I couldn't justify declining sex out of principle, only to do everything else. Plus, I had somehow resisted pounding her wet, little hole once, but I knew for certain I wouldn't be able to do it again.

We woke up together, and she made me breakfast in bed. She packed the last of her things, and we left her house at the same time. She was headed out on her cruise, and I told her I couldn't wait until she got back in a couple weeks, so we could pick this up again. She assured me that she really liked what was happening with us, and that she couldn't forget about me.

I thought I had it all worked out. I had passed over one night of sex in exchange for continuous prolonged sex upon her return. She was going on this cruise with her mom and sister, so the possibility of never seeing her again never crossed my mind.

The weeks went by, and I hadn't heard from her. There was no return to my phone calls. So much was going through my head, including "Holy shit, what if she's pregnant, and doesn't know how to tell me?"

Eventually when we talked, she admitting to meeting someone else. Her mom, of all people, had brought along someone she wanted Alicia to spend time with, some kind of re-connection with an old family friend. Alicia told me she was just looking to have fun, and not anything serious. In reality, she was young, and had no clue what she wanted. I just wish she would have told me that a couple weeks ago, so I could have fucked the shit out of her at least that one time, instead of getting her warmed up to fuck someone else on vacation.