When I first started this journal, I was wondering if I should include anything from previous relationships. Yes, believe it or not, a jerk like me has actually had a few serious ones. I was thinking I might take a favorite or two from each and include them, even though they occurred before I began my collection. I might still do that, I don't know. But I do have a journal entry for one of those women that definitely belongs in here.
Now I've never been one to make booty calls to ex-girlfriends, but I'm not one for burning bridges either. And if there's anything better than sex with an ex, it's getting your cock sucked by an ex. Especially when she's good at it, as Cheri most definitely is.
Cheri was quite a bit older than me. In fact, she's largely responsible for my older woman fetish, because she told me that it was much easier for her to go to bed with a man than give him head. She also told me during our two year relationship that she had given me more head than any other man she had ever been with. And that included quite a few serious relationships and a ten year marriage, so it wasn't like she was inexperienced. That's a bit of an ego booster, even if you're ordinarily modest.
Cheri was tall, big breasted and had incredible legs. Great hips too. Her auburn hair fell straight to her shoulder. One of the things I appreciated most about her is that, even though she was comfortable wearing sweats or jeans, she was equally at ease in skirts and dresses. She had a collection of skirts that were deliciously tight around her ass that fell temptingly above her knees. She liked wearing high heels, too, which made her ass look even better.
Our sex life had been pretty awesome for most of our relationship. It wasn't uncommon for us to spend an entire Saturday in bed, licking, sucking and humping each others brains out. She was a great lay and no matter how many times we did it, she always seemed to want it one more time.
Cheri was also a terrific at giving head. She had told me once that she didn't like to give head to most men. Not because she didn't like the act itself--which she did--but because she was a very proud woman and men often made her feel cheap and degraded afterward. She didn't have that problem with me and so she lavished her oral skills on me frequently. There was a stretch of several months that she stayed over almost every night and most weekdays she would blow me before I left for work in the morning.
While things in the bedroom were great for us, we had plenty of issues outside of it that even awesome sex couldn't overcome. We split up after a couple years, but managed to remain friends. Most of our contact was through email or a phone call, but occasionally we'd get together for lunch or drinks. For the most part we kept it platonic. For the most part, anyway.
On her birthday I was going to take her out for dinner, but our plans got changed. Cheri's a part owner in an artsy little boutique and one of her employees called out sick, and she got stuck working until closing. So I brought sandwiches and a cupcake with a candle in it to her just before closing time.
We sat in the back of the shop, ate and talked for a bit. Then she had to go to the front to lock up and make sure the girl working the register cleaned and ran the vacuum before going home. When she returned to the back room, Cheri had a devilish look in her eye. It was a look I'd seen many times before and I knew at the very least, we'd wind up making out before I left.
There was soft muzak playing in the shop and she coaxed me to my feet to dance with her. Actually, it wasn't dancing as much as it was pressing our bodies together and swaying to the beat. We kissed a few times, each one a little more passionate than the last until our tongues were dancing between each others mouths. Then our hands started running up and down each others bodies. I slowly ran my hands up from her hips to her waist to her shoulders, gently brushing the sides of her ample breasts on the way.
"Mmmmm..." she purred, running her own hands over my back. The kisses got deeper and wetter and our hands started roaming to more erogenous areas. When we heard the vacuum cleaner go on in the front of the store, Cheri slipped a hand down my pants and grabbed my stiff member.
"Does Santa want to come out and play?" she whispered in my ear. That was our euphemism for a blow job. I don't remember exactly how it started, but it had to do with a punch line to a dirty joke about Santa coming down the chimney. Now you might think she meant we'd go to her place or mine, or at least wait until the girl out front finished and went home. But I knew Cheri and I knew she meant right now.
Cheri was squeezing and stroking me in my pants, waiting for me to answer. She loved making me tell her that I wanted it. I could hear the vacuum running out front and I could feel how hard I was getting just thinking about Cheri's mouth closing over me. It was a pretty easy decision.
"Yes," I breathed. "Yes." That she would go down on me when someone was in the next room, could look in back at any moment and catch us, had me pretty wound up. Almost too wound up... I didn't want to cum quickly and ruin it. But my cock felt ready to explode in her hand as she slowly squatted down in front of me.
Cheri deftly unzipped my fly and pulled my pulsing shaft out. There was already a bead of precum on my head which she deliberately licked away.
"Mmmm... you taste as good as I remember," she murmured and then slipped the head of my cock into her mouth. She probably realized how turned on I was and wanted to savor it. At the very least, she didn't want me to cum quickly and spoil the fun. So she went very slowly up and down my rod a few times and then paused.
"I've been good this year, Santa. What are you going to give me?" She took me in her mouth again and bobbed a few more times. "Gonna cum down my chimney?" Cheri was killing me and she knew it. She gently licked each of my balls in turn, then she grasped my shaft and squeezed. Another drop of precum glistened on my head which she once again licked away.
Looking up into my eyes, she opened her mouth wide and extended her tongue beneath my shaft. She raised herself up under it and took it into her mouth, keeping her eyes on mine the whole time. There was always something magical about Cheri's eyes looking into mine while giving me head. It was a look that somehow conveyed her intense pride and self-confidence and at the same time said she would do anything to please me. I guess what made it magical is that she was a woman who didn't crave attention or need acceptance. Whatever she did for me was because she wanted to.
Cheri's lips closed around my cock and she started bobbing on it. She was squatting in front of me in her high heels, her hands grasping the outsides of my thighs as she slid her lips up and down on me. I was about to push her away because I was too close to losing it, when the vacuum cleaner suddenly shut off.
"Cheri," the girl from the front called. Her voice was very close. I quickly turned away from Cheri and tried hurriedly to tuck myself back into my pants, which isn't easy when it's hard and throbbing. I think I was still zipping my pants with my back toward the doorway when the girl walked into the back room. Cheri was pretending to look for something on the shelf next to where she was squatting, but I don't know if the girl bought it. Think about it: you walk into a room and a guy has his back to you as he's zipping up his pants and a woman is squatting on the floor a few feet from him. You don't have to be a rocket scientist to figure it out.
