As the saying goes, fool me once, shame on you; fool me twice, shame on me. Almost a year after my ex-girlfriend Jennifer broke up with me without so much as giving me a reason, I hastily forgave and forgot, and we were dating again. Without going into the details, the second run at a relationship lasted for an anxious three months before ending the same way the first try had. I still remember holding the phone to my ear, bewildered after Jennifer hung up following breaking up with me for the second time. Once again, I wasn't even given a reason.
There was no way, I thought, that the bitch would fool me for a third time. Almost two years passed before I even saw Jennifer again, and I had intended to keep that streak going indefinitely. However, she eventually did cross my path again, and the circumstances surrounding that meeting were a little bizarre. I even suspected they were not coincidental. Not only did Jennifer find out where I worked, but she stopped by and asked for me specifically, even though she knew my department had nothing to do with the service she claimed she needed. I was immediately taken back when I saw her, not expecting the visitor to be who it was. I wasn't at all happy to see her, so I calmly referred her to the proper staff member and quickly left her there.
Jennifer would not be denied, however. She had held onto my phone number for all that time and texted me that night. The jist of what she had to say was that she wanted to be friends again but still stunningly didn't seem to understand that she had done anything to hurt me. I inevitably shared my feelings with her, at which point she did ask for my forgiveness. I was OK with forgiving her but wasn't too interested in being friends, seeing as I had trusted her twice already and she had hurt me both times. I was ready to once again close the book on that chapter of my life until Jennifer pulled out the card that few men could refuse.
"What if I told you I really want to have sex with you? Just fuck me, one time." She had my attention.
Just because we dated twice for a combined four months didn't mean we'd slept together, and we hadn't. I'd wanted to, though. I still did, actually, but not for the right reasons. I guess I hadn't really forgiven her and was still kind of bitter. I liked the idea of letting her close to me physically, like she had done to me emotionally, and then dropping her as a form of payback. It was admittedly a selfish, immature motivation on my part. I deserved for it to backfire like it would.
On top of it all, Jennifer was really sexy, and I could only imagine she was a good fuck. She was 5'8" and thin; thinner, now, in fact, than I remembered her. She must have started working out again. Her bright brown eyes and long, light brown hair could make my heart melt, too. Her best physical qualities for sure were her C-cup boobs and, of course, her awesome tight ass. She had about as rocking a body as any 30-year-old I knew.
My mind ran wild with possibilities when I fantasized about nailing Jennifer. I had a pretty perverted mind that could conjure up some really debased fun I could have with Jennifer's sexy body, making it even harder to refuse her tempting offer. I decided that as long as I could stay in control of this casual affair, it would be harmless to sleep with her. After all, I had done some things that I was much less comfortable publicizing than simply what would amount to me as break-up sex.
We did end up having sex, in fact, and did so without so much as a real date. In the past, our actual dates had gone well, but, frankly, I had wasted enough time and money on her. Therefore, we cut out the formalities, and she met me at my apartment late one warm night toward the end of autumn. When I greeted her at the door, she was wearing a tight, long sleeve, low-cut gray shirt under which nothing was worn to cover the cleavage of her lovely breasts. I'd never gotten that good of a look at her rack when we were dating, so I was sporting a nice bulge in my pants pretty quickly. With the top, she wore simple blue jeans and black slip-on shoes.
In about the same time it took to describe her attire, the clothing was on the floor. Jennifer asked where the bedroom was and then made a beeline for it, scarcely looking over her shoulder at me as she pulled off articles of clothes all the way from my front door to the bedroom. I stood like a statue as I watched her go around the corner, into the room just before she tossed a black bra into the hallway.
I snapped to it and hurried down the hall and into my room to see Jennifer grinning playfully as she was already up to her chin under my comforter. At that point, I finally disrobed as well. Those final few minutes leading up to intercourse were a blur. I joined her in bed as she sat up, pulling the comforter up in order to let me in. My cock shot to full attention as soon as I saw her naked body, which was every bit as hot as I had imagined it. Jennifer knew she had me in that moment, her sly, seductive grin betraying her confidence as she watched my eyes drink in her luscious curves and sexy features - including those wonderful boobs, which, when bared, were every bit as arousing as I'd hoped.
Her hand was on my cock before I had even settled in beside her. I wanted badly to be in control and not give the girl who broke my heart the satisfaction of winning me over in any way, but the instant her warm, soft hand made contact with my flesh, I let out an involuntary moan that conveyed I had all but lost the upper hand. Jennifer let out that cute laugh of hers and went to work on my dick, sliding her hand up and down the shaft as she stroked me to insure I was totally hard for her. Of course, she knew almost right away that I was good and ready to be inside her.
I stayed still and watched as Jennifer pushed her hair back over her right ear and lowered her head down to accept my cock into her mouth. I felt a strange sense of powerlessness as my ex began to suck me off. As soon as the head of my cock slipped into her mouth, she pressed her lips around the phallus and pushed her head down until the entire shaft was inside. Jennifer didn't so much as gag as she held my entire member in her mouth for a second, the tip of which poked at the back of her throat.
Again, so desperate to for once have the upper hand with this girl, I tried to suppress a moan but failed. The corners of Jennifer's mouth pointed up a bit, and her eyes met mine as she smiled as best she could with a mouthful of cock. Then she slowly pulled her head up, my cock sliding within her mouth until my cock was out of her mouth entirely, exiting with an audible pop, at which point Jennifer inhaled deeply. I groaned again, and before I could regain composure, Jennifer threw her head back down and took my prick right back in.
Without further adieu, Jennifer's head bobbed up and down on me, her lips and tongue expertly pressing against my shaft as she blew me. I gripped the sheets and finally managed to keep it together, simply sighing while the pretty girl sucked my cock. To date, I had done some pretty hot and debauched stuff with girls, so I didn't know what it was about a simple blowjob from Jennifer that had me overwhelmed with her, but I was very much at risk of falling into this girl's trap for the third time.
