I arrived a few minutes early. I counted that as a check in the excellent block of my mental report card. It was my understanding that the restaurant was a few blocks from her hotel. Would she walk or drive? What did I care? With my luck, I’d be the one sitting in the restaurant watching my car getting the business end of a tow truck. Just then, in she came. She looked relatively the same as she had twenty years ago. Her smile lit up the room when she recognized me. I couldn’t help but give her a kiss on the cheek and step back. We looked at each other, and I was amazed at how good she looked. I could only imagine what she was thinking about me. We spent a few moments with introductory chatter and then were escorted to our table. I helped her with her coat, and the whiff of perfume made me want to just drop the coat and start nibbling on her neck. Her outfit complemented her figure and was quite classy. We sat, and the conversation was as fluid as if a day had never passed. I was on my best behavior and trying very hard to be charming. I built up enough nerve to ask about any possible relationships. That was when the waiter decided to walk up and take our order. His tip had just taken a turn for the worse. I placed another favorable check on my report card by ordering the drinks and meal for both of us. As the waiter stepped away, T began a funny anecdote about the last time she had that meal. Come on, cut to the chase. I’m going to laugh regardless of what happened. I wanted to get back to the conversation about relationships.
She knew what I wanted to talk about because after her anecdote, her voice and head dropped. In a soft voice, I informed her that we could talk about anything. T then explained that she recently had finalized her divorce. She had come to realize that her ex was never going to grow up and thought she should end it before they became enemies. She further explained that the divorce was amicable and that she was over it. I then asked about previous love interests. It appeared they were few and far between. She was like most business-oriented women, and her sex life had suffered while she was climbing the ladder of success. Our meal arrived, and more jovial topics prevailed. The coy eye contact and cheeky smiles were a little uncomfortable, but we were both taking it well. The meal was just about done, and somehow the status of my relationships finally came up. Would the truth really work in this situation? Did she really need to hear the truth? For her “own good,” I decided to skirt the truth and tell her what she wanted to hear. It just so happened that what I told her made me available for sex if she felt so inclined.
The meal was done, and I helped her with her coat. We exited the restaurant and stood outside for a few minutes talking. When it appeared we were done, I kissed T on the cheek. The pause and eye contact afterward begged for something more. I then gave her a tender kiss on the lips. I could feel her moist lips kissing me back. I asked her how she was getting back to her hotel. She said she had walked. I certainly could not allow her to walk back alone, and so the slow stroll toward ecstasy began. The street was quiet, and it was beginning to drizzle. We walked, looked in the store windows, and talked about life. A life when things were simpler. Like when we were teenagers. And there we were, right where I wanted to be. At her hotel and talking about sexual encounters. The drizzle slowly picked up to a solid rain. At least the weather was on my side. As if she were reading my mind, T invited me up until it stopped raining. As I was walking through the lobby and stepping into the elevator, I knew I was crossing the line. As we were going up in the elevator, you could cut the tension with a knife. The conversation became strained. Should I excuse myself? I could feel the brain center in my pants setting up shop, and the signals from the big head were shutting down.
We exited the elevator and were walking toward her room. I could feel that my clothes and face were damp, but my mind was focused on looking at her ass swish back and forth beneath her coat. We entered the luxury room, and I was impressed. “Very nice,” I muttered. My mind was struggling for something intelligent or witty to say. As she threw me a towel, I took off my coat and shoes. She suggested that I turn on the television while she got comfortable. I found something mildly entertaining to watch and stretched out across the bed. Then I heard the shower running. Should the shower be running? Was she actually going to get naked with me roaming through the room? Good Lord, was there a chapter in Dating for Dummies that dealt with this kind of situation? I didn’t know what else to do but wait for her next move.
She came out of the bathroom wearing a robe, a towel on her hair, and carrying a bottle of baby oil. She sat on the edge of the bed, opened the baby oil, and started rubbing it on her feet. Being a gentleman, I insisted that she sit back and allow me to take care of that for her. After all, it had been a fantastic evening thus far and it was all due to her. The mental report card just received another excellent check. She agreed and sat back against the headboard. During her shifting, her robe came open slightly and I could see that she had on only a pair of panties. The erotic visions were rampantly running through my mind. I poured some baby oil into the palm of my hand and began an erotic massage on one foot. I knew that once my oily fingers passed through her perfectly shaped toes, something was going to happen. As sensually as I could, I rubbed the oil onto her foot and up her calf. In addition to her inhibitions, her topic of conversation relaxed. T then informed me that since “us,” no man had ever treated her with such tenderness. Despite accumulating some skills with regard to sex, she still embraced our awkward encounters. My concern for her needs and pleasure had never been duplicated or replaced. I felt a bashful smile envelop my face. Luckily, her eyes were closed and her head tilted back because I felt at that moment that I was unable to look her in the eye. I merely thanked her for the comment and poured more oil for the other foot. I didn’t think it was possible, but my skill level for erotic massage rose along with my penis and her robe. I found my oil-rich hands sliding above the knee and heading for the upper thigh. I felt her legs opening, allowing me access. As my hand brushed against her panties, I could feel heat and moisture. Unless one of us came to our senses, it was going to happen.
I decided to give her an opportunity to cease our course of action by standing and removing my shirt. Instead, she used that moment to remove her robe and help me with my pants. As she pulled my boxers down for me, she came face to face with a part of my anatomy that she hadn’t seen in two decades. She took my package into her hands and carefully pushed back my pubic hair. Her mouth opened, and she used her tongue like a shoehorn to slowly insert my cock into her mouth. This was a skill that had improved since last we met. She teased and sucked me to full length and stopped to admire her work.
“This is the dick that started it all,” she said.
The fact that she wasn’t laughing and shooting snot from her nose was a victory for me. I looked at her body and just wanted to cherish it before I ravished it. So I asked her if she would allow me to finish my massage.
She looked at me and said, “If that’s what you want to do, fine.”
She slid back onto the bed and offered herself to me. I grabbed the oil and finished her legs and began on her arms. While touching her body I was finding it hard to put more than two words together between gulps. Completing sentences was totally out of the question. When I finished her arms, I placed a small amount of oil on her stomach and began small circles until I reached her breasts. Normally, I preferred larger breasts, but in her case I was more than willing to make an exception. With each slow pass of her nipples, each of us released a low moan.
Realizing that I needed to catch my breath, I asked her to roll over. That was truly a mistake. I hadn’t discovered until that moment that she was wearing a thong. The sight of those magnificent butt cheeks in that thong would have caused a coronary in a weaker man. I collected myself along with the bottle of oil and continued my task. I started with her back because I knew touching that apple bottom would have to be last. While I massaged her back, she continued to lament about our last sexual encounters. I knew that they had meant a lot to me, but I was never aware of the impact they had on her. By the time I rea
ched her buttocks, I was compelled to reveal my unrelenting desire to touch her ass. She laughed and recalled the many times in our youth I palmed her ass while playing and especially during sex. She knew I just couldn’t keep my hands off her ass. She said that was probably why she started wearing thongs. I could no longer resist. I slipped my fingers under the waistband of the thong and slowly pulled it down. Watching the garment pop out of the crack of her ass was a bonus. She rolled over, and our eyes met. I lowered my body onto hers, supporting my weight with my arms. Our kiss was a passionate one that contained many messages of desire. Then T reminded me of the time I tried to fuck her tits. That was truly a sad attempt, but since we were just learning, it wasn’t as devastating as it could have been. T said she knew how much I loved large breasts and that I must have completed that act with someone. She wanted to give me that opportunity again.
She reached for the oil and rubbed some across her chest. Using her oily hand, she stroked my cock to a full and throbbing mass. She lay back and asked me to straddle her. Her breasts were not ample enough to wrap around my cock, but their appearance was quite capable of keeping me erect. She rested the heel of her palm on one and placed her fingertips on the other, leaving a space for me to slide my cock under her hand. I grabbed on to the headboard and hung on for the ride. I closed my eyes and made love to her hand and chest. The sensation of my nut sack dragging across her chest was mind-shattering. The oil and her hand were working like a charm. The occasional glimpse of her face and nipples brought me to my peak. I felt the end was close. My pace slowed, my heart raced, and my moans grew louder. At the moment of explosion, she placed a firm grip on my cock and pointed it toward the underside of her chin. I opened my eyes in time to see the first load deflect off her chin. The second and third streams weren’t as strong and dribbled across her chest but were just as satisfying. As my juices began to pool into a notch in her neck, she pulled me toward her mouth. I inched forward and tilted my body so that she could squeeze the remaining droplets onto her outstretched tongue. From the look on her face, I couldn’t tell which one of us enjoyed it more.
After a brief stint of unconsciousness caused by an excess amount of ecstasy, my hands began exploring her soft curves. I didn’t know if or when I would get another opportunity like that, so I had to admire that booty one last time. As I picked up the baby oil from the floor, I coaxed her to roll onto her stomach. I held the bottle so that the oil would drip out onto her sexy mounds. The droplets slowly ran off the mounds in every direction. My widespread fingers savored every inch as I massaged the oil into her skin. My hands loved the splendid symmetry of her soft, plump hindquarters. My thumbs came together at the point where her inner thighs and butt cheeks met. They dug into the folds of the skin and slid upward into the split of her ass. I paused momentarily to explore the edges of her anal opening. The low moan indicated that the action needed to be repeated. This time when I stopped on the rim of her anal opening, I carefully inserted both thumbs into her. From the relaxed response, I could tell this action was not foreign to her. I teased, twisted, and tugged the sphincter muscle until I could fully insert both thumbs. I was so focused on what I was doing that I failed to notice that her breathing was labored and her pleasure was peaking. I thought I was being suggestive and/or talking dirty when I said, “You really need my dick in your ass.”
I was shocked at the response: “What are you waiting for?”
On that note, I decided to terminate my half-assed proctology exam. I pulled my thumbs out one at a time, stood up, and thoroughly oiled my cock. T positioned herself as if she had done this before while being tied to the bed. Her legs and arms were pointed to each corner of the bed and slightly squirming. From a kneeling position, I propped myself up with one hand while using the oily hand to place the tip of my cock on her backdoor. As the head penetrated, she reached back with both hands and spread her butt cheeks as far as possible. Little by little my cock disappeared into her. Her grunts concerned me but were quickly dispelled when I heard, “Fuck me.” Once I was fully inserted, I supported my upper body with my fully extended arms and hands. The middle of my torso was grinding on her plump ass with each downstroke. I could feel her sphincter muscle constricting around my throbbing tool on the upstroke and my pubic hairs rubbing against her ass on the downstroke. As we pounded again and again, there was no doubt our lust could be heard in the adjacent rooms. When I heard her reaching her climax, I pushed down as hard and deep as I could. I slowed my pace and rotated my hips until she could catch her breath. The complete submission and surrender of her body to me was utterly fantastic. Once we were both ready, I picked up the pace until we both peaked at the same time. There wasn’t much left, but I could feel the surge from my balls go through my cock and leak out of the tip as it came to rest deep within her. Withdrawing my manhood and watching it dangle and drip onto her ass was very different from anything we had ever done.
I rolled onto the bed beside her and stared at the ceiling. I was reveling in the sensations flowing through my cock and feeling the sweat drying on my body. T rolled onto her side and commented on how much better we both had become at sex. She snuggled up close and started playing with the hair on my chest. I put my arm around her and stroked her soft skin. We just lay there and reminisced about the old days well into the night. I didn’t want to leave until she mentioned she had to get up at seven for a meeting. I got up and took a quick shower. When I exited the bathroom, T was curled up and asleep on the bed with the blankets at her feet. I covered her up, dressed, and left a note requesting that she call me whenever she wanted. I gave her a light kiss on the forehead and slipped out undetected. The walk back to my car through the mist just couldn’t last long enough. It was unfortunate that my mental report card and any other evidence would have to be destroyed before I got home.
NO COINCIDENCE
Anne Alexander
There he was again, standing downstairs in the crowd, watching the band, his face illuminated. It was the third time in a month she’d seen him at this club, and she was starting to think maybe it wasn’t a coincidence. She looked away for a minute, pretending to scan the crowd behind her for the friends who were supposed to meet her there. When she looked back, he was looking at her. Her heart leaped in her chest, and she smiled at him. He smiled back.
Well, she thought, this is how it all went before, too. I wonder if we’ll ever talk to each other. Do I have to make the first move?
So she did. She looked down from her spot on the balcony and waved, making it clear it was to him she was beckoning. He waved back, and she smiled again. The band launched into a faster song, one she always turned up and danced to in her kitchen. She started dancing now, moving her hips and flipping her hair, letting her eyes lock on his every once in a while. She raised her arms above her head and moved them, too. The next time she looked at him, his gaze was fixed on her. He was mesmerized. She felt amazingly sexy, dancing for him, so she kept going faster and faster as he watched. And even though the club was pretty packed, she felt like they were the only two people there.
The song ended, and she clapped and screamed for the band. As she glanced down at her mystery man, he was clapping too, but he was still looking up at her. She got a little embarrassed then and tried to compose herself. She turned her attention back to the band, which was getting into a slow, soulful song. She took a deep breath, then looked back down to where he was.
But he wasn’t there anymore. She scanned the crowd, trying to make him out, but she couldn’t see him. Damn, she thought.
“Damn. I blew it,” she said aloud to herself.
“Nah, I don’t think so. You’ve still got a shot,” a voice behind her said right into her ear.
She whirled around, and of course it was he. “Hi!” she said, slightly sheepish at being caught talking to herself but glad to be face to face with her mystery man after so much prolonged flirting from afar.
“Hi. I’m—”
“No, wait, don’t tell me ye
t. Keep it a secret,” she said, turning back around and resting her hands on the railing of the balcony. She reached behind her and caught each of his hands in hers and brought them around her, putting his hands on the railing with hers. He was right up against her now.
It’s pretty dark up here, she thought. A fair amount of people, too. I wonder how much I can get away with.…
She began to sway her hips to the music, and she moved her hands so that they were over his and caressed them lightly. She could feel the front of his jeans through the thin material of her skirt, and she was glad she’d worn it instead of jeans. Glad it was warm enough to forgo tights, too.
“What are you up to?” he whispered into her ear. She reached up and touched his cheek, holding him there by her face. His was slightly rough with stubble, and she liked it. She turned her head to kiss him quickly on the cheek, but he turned his head fast and caught her with his lips. She was surprised at first but then melted into it, opening her mouth slightly and letting his tongue in to touch hers. It was a soft, sweet kiss, but it got faster and more urgent quickly, until she was sucking on his bottom lip and he was nipping lightly at hers. She could feel the urgency elsewhere, too, as the hardness under his jeans grew and she rubbed her ass against him.
“Just getting to know you,” she whispered back, letting the tip of her tongue flick into his ear. She felt him gasp.
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