I was very nervous because I hadn't had a date since I'd returned from a very long deployment overseas. When the only people you see other than your buddies look at you suspiciously, your interpersonal skills seem to drift away.
So, I was more nervous than I'd been since I was a teenager. I'd met a stewardess through a mutual friend and she was drop-dead gorgeous. Tall, with long light brown hair, deliciously sexy legs and a smile that was hotter than the desert I'd just been in, Shelly was like a mirage. When I met her, I was immediately convinced I had no shot whatsoever, so I just joked around with her all night. Shockingly, we got along so well that I left that night with her phone number.
Since I was so nervous and had no decent civilian clothes, my friend Lorrie insisted that we go shopping on Saturday morning. I've always trusted her judgment, so we spent a lot of time wandering in and out of stores. More than once, when she bent over to pick something up during our shopping, I was reminded just how great an ass she has. She's a short woman, with dark brown hair she keeps short also. A regular schedule of exercise classes and yoga have kept her very fit.
Once, when she was checking the fit of a pair of pants, she was kneeling in front of me and tugging on one pant leg. Her hand slid up the inseam a ways and I nearly exploded right in the store. She smiled up and me and asked if they fit all right. To be honest, they fit very well, except in one area. As I looked down at her lips and big eyes, I remembered the one drunken night when she bragged about how good a blowjob she could give.
I had a sudden image of her fist wrapped around my cock, pumping it while her lips engulfed the head. Somehow, I was able to re-focus on the real world and agree that they fit pretty well. We headed back to my place and she insisted that I model the clothes for her, so that I would wear the right shirt with the right pants.
So, I changed and came out into the living room to show off. When I got into the room, her back was to me and she was bending over rummaging in her purse. Seeing that skirt stretched tight across her sexy ass made my pants seem just a little tight again. She stood up as she heard me and turned around. She smiled and told me that I looked great, and then made me spin round so she could check everything out. When I turned back, she had a little frown on her face. "Something doesn't quite fit right", she said.
She walked over and knelt in front of me, her hand running up my right leg and adjusting the pants. Then her hand ran across my crotch and she tried smoothing that down. Well, that only made it worse. She then unbuckled my pants and unzipped them. I was completely frozen as she ran her hand along my shaft through my boxers, but never said anything and never looked up.
She slid my pants slid down a bit and cupped my balls. My hard cock slipped out of my boxers, waving in front of her lips. As all the blood rushed around my body in waves, she ran her tongue along the shaft and looked up at me with a question in her eyes. I just nodded my head and she kissed the tip of my cock.
Wrapping her hand around the shaft, she kept looking at me as she slowly pumped it. Her lips were massaging the head and I was going crazy but completely unable to move. She kept pumping her fist as she lowered her mouth and sucked on my balls.
I couldn't help but groan as I experienced just how amazing her blowjob really was. She licked her way back up my engorged cock and slid the tip into her mouth. Now there was nothing slow about the work she was doing. That hand was pumping vigorously as she buried my cock in her mouth. I finally was able to move my arm and run my hand through her hair as she sucked my cock with her fist pumping it. I could hardly hold back.
She slid my cock out of her mouth and kept pumping it while she begged me, "Cum in my mouth, I want to taste your cum." Watching her fist pumping up and down, I felt a wave wash over me as she ran her tongue around the tip. I groaned, "Lorrie" and felt a spasm as my cum started squirting inside her mouth.
She looked up at me, still pumping her fist on my cock and sucking the cum out of it. She ran her cum-covered tongue along my cock, licking up some that had spilled down the shaft. Lorrie smiled and swallowed my hot cum in her mouth, then slid my slowly softening cock back into my boxers and zipped my pants back up.
"Much better," she said, "that fits much better. Oh, and now the pipes are clean." She winked, stood up and walked towards the door. As she opened the door, she looked over her should and asked me to call later to let her know how the date went. I was simply speechless.
Confused, I changed into some loose shorts because I had to head to the gym to meet my workout partner. I had no idea what I should be thinking or doing, except that I'd better keep to my schedule.
Annie and I had been working out together for a few years. We'd been part of a group of friends and I thought she was just dynamite. Of course, she seemed only to have eyes for one of my buddies, whom all those girls chased after. Both Annie and I had been laid off, so we bumped into each other at the gym during the day and then just started scheduling workout sessions to keep busy and fit.
On the weekends when I didn't have reserve duty we'd sometimes go on long bike rides, which I enjoyed for more than the exercise and the scenery we rode through. Annie had a great pair of legs from running a lot and seeing that bicycle seat nestled between her thighs always made me happy that she rode so fast.
I arrived at the gym a bit late, so she was already on one of the treadmills. Climbing onto the one next to her, I tried not to stare at her legs, as a similar distraction had already confused my day. They were great legs, though. I'd often imagined them wrapped around me or spread wide with me licking her hot pussy. Needless to say, I was distracted already.
As we trotted along, she asked all kinds of questions about my first date. She sounded almost as excited about it as I was and she had loads of advice for me. I'd always been a bit less-than-suave, so any help was going to make a huge difference.
Annie hadn't had a good date in ages and complained that she wasn't sure she knew how to fuck anymore. I remember watching her lips form the word "fuck" and being mesmerized by it. As I listened to her talking about each of the odd guys she'd had one disappointing date with, I imagined her screaming, "Fuck me" or whispering "fuck me harder" or groaning "fuck my pussy".
I slowed down on the treadmill because I'd gotten so hard again that moving quickly was not very comfortable. We kept talking and I really tried not to think about it, but I just kept seeing those lips forming the word "fuck".
It probably didn't help when we went over to stretch after our workout. I made sure not to stand behind her when she touched her toes, but sitting down in front of her while she was doing it and talking to me, I found myself eye-balling her nipples as her top opened a little wider during her stretch. Her nipples were hard and a dark red, perched on small, round breasts just big enough to fill your hand or mouth.
I imagined circling one of them with my tongue while I'd slide my fingers in and out of her tight pussy. This meshed well with imagining her begging "fuck me, please fuck me." I blinked a few extra times and was able to finish stretching, despite one muscle seeming not to loosen, but instead get harder.
Annie had been having some computer problems, so I followed her to her apartment to have a look at them. She complained that she'd been getting a lot of popup ads, especially since she'd been using a file-sharing site. When we got to her apartment, I sat down in front of the computer. Right after we turned it on, windows started popping up, showing naked women, many of them tied up and sucking on dildos or kneeling in front of some guy. Again, she said "Fuck!" and my mind spun.
She leaned in to click the mouse and rubbed her breasts against my shoulder. As she worked the mouse more vigorously, she leaned further forward and occasionally rubbed them against my face. Not wanting to accidentally do something I shouldn't be doing, I turned the chair a bit to let her in closer.
I would say that it was unfortunate that it didn't quite work out the way I intended, but since she ended up basically in my lap with her tits pressed into my face, I don't think I can complain. I don't think I intended to have her nipple in my mouth, but it ended up there. Since I'd already been imagining this, I knew exactly what I wanted to do.
I nibbled gently on her nipple through the top she'd been wearing at the gym. She let out a slight gasp of surprise, then held the back of my head, pressing her tit into my mouth, and whispered, "don't stop." She muttered something about her top being too sweaty and peeled it off, her dark hair cascading down to her shoulder as she freed her lovely tits. Her nipples tasted even better than they'd looked and I licked and sucked on them hungrily.
She whispered, "You'd better not try this on that first date" while I nibbled on her swaying breasts, kissing and licking her nipples. She groaned and whispered in my ear, "...and you'd better not slide my shorts off, because you wouldn't do that on a first date." So, I slid her shorts down and she slipped them off while kneeling on the chair, hovering above me.
"...Or finger her pussy..." she moaned. Slipping her thong aside, my fingers rubbed an already wet pair of pussy lips. I wanted her to beg to be fucked, so I ran my fingers around her clit, feeling her buck on my lap as the waves of pleasure crashed inside her.
"...Oh, and tying her up with ropes from her desk drawer would be wrong..." I reached in and grabbed the ropes, lashing her hands together. She got up and bent over the desk.
"...And you sure wouldn't want to bend her over like this... not on a first date..." I stood up behind her, dropping my shorts to the floor to free my once more hard cock. I rubbed it all over her ass and watched her quiver when I slid it down along her asshole.
Then she said the word I'd been so mesmerized by, "oh, please fuck me" in almost a whisper. As my cock slid between those wet and hungry pussy lips, I reached forward and grabbed her tits. I felt the next wave inside her and slowly slid my cock in and out while she shook. The ropes kept them together, but her hands were clenching and un-clenching as I drove my cock deeper into her tight pussy.
"Yes, fuuucck me!" she groaned. Playing with her nipples I kept grinding my cock into her. Her pussy was squeezing my cock harder all the time. She started rocking back to meet each thrust and screamed, "Fuck me harder!" I stood up, gripping her hips as I plowed into her tight pussy.
I spanked her hard and she squealed in pain and pleasure. I spied some oil on the desk and picked that up, squirting it all over her ass. She moaned, "Yesssss" and then whispered, "fuck my ass, please fuck my ass." I slid an oiled finger inside her while my cock slithered in and out of her dripping pussy. Pressing her face to the desk, she managed to whisper quietly, "...bigger, I want more...." And I slid a second finger inside. Those hands I'd tied together pounded the table as her eyes squeezed shut and her mouth contorted.
She arched her back and begged me again, "please fuck my ass". As my cock slid out of her pussy, she groaned and spasmed for a second. I nudged her tight hole with my hard cock and she spread her long, sexy legs a little wider. Her tight hole slowly widened as my cock entered her ass. I heard her hiss, "yeeesssss". Her hole was so tight, I wasn't sure I'd fit all of my cock inside her, but she kept pushing back harder and moving her legs to open that sexy ass wider.
"Fill my ass with cum, Dan," she pleaded. Holding her hips, I was having a hard time not exploding inside her. I rocked her back and forth, my cock ready to burst as I fucked her ass. I watched her ass bounce every time I plunged my cock deep inside her and felt her squeezing my cock. Gripping her hips, I guided my cock in and out.
"Oh, God, I'm gonna cum!" I screamed and she bounced back against me harder.
"Fill me up! Fill me with cum! Fuck me!" My cum started spraying inside her tight ass. I just shook from the waves of ecstasy, feeling her tight ass squeezing the cum out of my cock.
I slowly slid back into the chair. Annie looked up at me from her desk and said, "Don't even try that on the first date." She crawled over and caressed my cock with her hands as I untied her. She leaned forward and kissed my cock. Looking up into my eyes, she said, "Make sure you come over here tomorrow, because I'm not through with you."
As I got ready for my first date, my mind was utterly confused.
As I pulled on my new pants, I kept thinking about Lorrie kneeling there sucking my cock and stroking it until I came inside her mouth.
When I went to my computer to double-check the directions to Shelly's hotel, I remembered filling Annie's tight ass up with my cock and nearly surfed to a few porn sites since I was horny again.
Somehow, I managed to get myself together and over to the hotel. I called Shelly's cell phone and she told me she wasn't quite ready, so I should come to her room while she did the finishing touches.