I met Carol during a summer internship and my handjob obsession vaulted to new levels. My undergraduate years did not include a lot of sexual partners though I found opportunities to hook up here and there. It was typically just regular sex and, of course, it was always a fun and welcome relief but I was not the sort to hook up every weekend or have a steady girlfriend.
When I first saw Carol at my bank that initial summer of grad school, I was immediately attracted to her. She had dark hair, gray eyes, a nice figure, and big tits. I made a point of stopping by the bank often to have an excuse to see her and engage in small talk while getting the chance to sneak a look at her tits which were sometimes nicely accented by the dress shirts she wore. Fantasies of seeing her naked and having sex with her, especially of cumming on her tits, began to dominate my masturbation sessions. Then, after a couple of weeks, I was introduced to her through a mutual friend who told me he knew her when I brought her up during conversation.
The timing worked out perfectly as the bank was having a celebration dinner for a retiring manager and she needed a date. Through our mutual friend, we got in touch and she invited me to come as her guest. Yes, I jerked off several times imagining spending time with her outside of her work and while I didn't figure things would get sexual right away, I could certainly fantasize about it!
The evening of the dinner rolled around and I met her at her place, a small basement apartment in a single-family home where she had been renting by herself for a few years. She wore a classic little black dress and looked fantastic with the fairly deep neckline showing off her cleavage, far more skin than I had seen her display at work! I had to focus elsewhere to avoid getting an erection that would have been painfully obvious in my suit pants. We chatted for a few minutes then headed to my car for the short drive to the restaurant, making more small talk finding out about one another and a little about our backgrounds and work lives.
She had moved out of her mom's home right after high school and started working at the bank where we met and had been pretty much on her own since then. She took a few college courses here and there with the idea of eventually getting a degree in finance but paying her own way made it slow going. After getting to the restaurant, we met up with her co-workers and had a nice evening hanging out over dinner and just talking as we got to know one another better. She and I engaged in light flirting during dinner and discussed meeting our mutual friends at a local club after we left the dinner so we could continue the evening together.
After an appropriate length of time to keep up appearances, we headed to the club for some drinking and dancing. Our friend and his girlfriend kept stoking the flirtation which made things a bit more interesting for me and, I think, for Carol. Dancing together had certainly had the effect of heating things up, too. Having a few drinks had loosened Carol up and she was easily laughing and showing interest in me. We got a bit more relaxed with our personal space while dancing and didn't make any attempt to hide our growing arousal with one another and we readily ground into one another and shared some kisses while dancing. I was excited that things were moving quickly and in an unexpectedly positive direction for the night to end with sex!
When we got back to her apartment, she invited me in and of course I went. We had another drink and sat on the couch talking more. We were seated close together and eventually started kissing again. Very quickly, we both started letting our hands roam and, you guessed it, I went right for her tits, caressing those mounds through her dress. She took a little more leisurely approach working her hands across my shoulders and chest, slowly moving towards my unabashedly hard cock. She paused to comment on the feel of my physique and said she could tell I had played sports in college because I was still in very good shape. I thanked her and tried to show my appreciation by kissing her more deeply and sliding a hand under the hem of her dress onto her thigh.
Soon after, as she began massaging my cock through my pants, I made the move to unzip her dress and she shifted to allow me easy access. This was going right where I hoped it would! As I slid the dress off her shoulders, I was treated to the sight of her tits in a low cut strapless bra holding them up as if being offered for my private enjoyment. Both of my hands went straight to them and began caressing them as I slowly pulled the bra down to reveal them completely. She gasped slightly as the fabric slid across her erect pink nipples and I saw the flesh of her areolas rise up with goose bumps, revealing her arousal.
Carol started unbuttoning my shirt as we continued to kiss and as I fondled her tits, eventually getting to the point we had to stand to finish getting it untucked from my pants. As we stood, her dress fell to the floor and she was before me in just her heels and small pair of black thong panties. I paused to take her in with my eyes, enjoying the sight. She was not athletically thin and toned, but was in no way overweight. She was taller at about 5' 8" and had a very soft look about her well-shaped and curvaceous form. I was going to enjoy this!
She pulled my shirt off, ran her hands across my chest and down my abs to start working on my belt and pants. In a moment, as I kicked off my shoes, she slid my pants off and took my boxers right down with them, leaving me totally naked with my cock proudly standing up pointing at her. There was a little stream of precum that had streaked out as my boxers came off and it slowly slid down the underside of my quite swollen head. She smiled and reached her hand out to slowly feel my cock, running her hand up and down the length of my shaft. I pulled her closer and began kissing and licking her tits, gradually working towards her nipples, giving each one a few minutes of swirling with my tongue and sucking them into my lips. She moaned as she continued to stroke my cock and we made our way back onto the couch.
I pushed her back and began kissing down her stomach making my way towards her panty covered pussy. Though black, I could see a very clear wet patch on her panties and I hooked a finger under the front and slid them to the side revealing her nicely trimmed pink folds. I kissed my way up and down her pussy and slowly spread the lips and slid my tongue along the opening. She bucked her hips towards my face, meeting my tongue and began to flick it across her clit. As Carol moaned and pulled my head into her pussy, I went to work in earnest and brought her to orgasm fairly quickly.
With her juices on my lips and face, she pulled me towards her and asked me to stick my cock in her. I readily agreed and her pussy, though freshly warmed up, had to stretch to accommodate my generous erection. I eased in and out slowly, getting her slickness spread over my whole shaft, and then after a few moments, plunged all the way into her wet slit. She gasped and arched her back, reminding me that I needed to get to her tits. As I began pumping into her pussy, I leaned forward and grabbed her tits, sucking them alternately as we fucked. In just a few minutes, she came again, her pussy muscles squeezing my cock as she coated me with a fresh flow of her juices.
I was nearing my own climax and began pumping her furiously as I leaned back and gave her every inch I possibly could. As my own orgasm neared, I realized I needed a plan because I had no idea if she was on birth control or not and I didn't want to risk filling her with my load. It didn't take me long as I gazed at her heaving tits, still wet from my licking and sucking, and pulled my cock out and aimed it right at those beautiful globes. The first rope shot out with such force that it sailed over her head and hit the couch, trailing off on her hair. I aimed a little better and the next several shots all hit her tits and splashed across them and her neck. Each subsequent spurt was a little less forceful and ended up painting her torso until at last I was dribbling onto her bush.