Loading...My boyfriend broke up with me several months ago. At first, I was heartbroken because I thought he was the one I was supposed to be with for the rest of my life. As time went on, I realized that I was better without him. He only called me when he needed something; he rarely checked on me when I was sick. And the worst part was that he was abysmal at sex. He fucked me like a jackhammer, which never brought me to orgasm. He never went down on me.
I dated a few guys after he dumped me, but we didn’t have sex. I wanted to wait until I was part of an official couple before I went that far with a man. The whole “don’t give away the milk for free” thing, you know. My vibrator and I became frequent friends during my long dry spell. I would gasp with orgasm by using my fingers and vibrator, enjoying the pleasurable release before I fell asleep. But I missed the feel of a living, breathing man with a warm dick and someone that could hold me afterward.
I usually cruised the dating websites like Match.com and eHarmony.com to look for a compatible man. One night, though, I realized how much I wanted a man next to me. I wanted to be fucked and pleased. I wanted to be eaten out, something my ex-boyfriend refused to do. It had been five years since I had been eaten out. When I was with him, I could pretend that it didn’t matter because I did have his body next to me. Now, though, I realized how much an orgasm with a man meant to me.
That lonely Friday afternoon I decided to abandon my usual dating websites, where everyone claimed to enjoy long walks on the beach and leisurely gourmet dinners. I wanted something different. I wanted to meet a man for some good old-fashioned intimacy with someone who knew how to please a woman. I signed up at CasualEncounters.com and started to sift through the men’s ads.
I gravitated toward the older men’s section. Maybe I knew that these men had the experience to know how to please a woman. Maybe I knew that being 25 years old and reasonably attractive meant that I would have more men vying for my attention. I searched through the profiles and was figuring out which man I would choose to contact.
One gentleman interested me in particular. His ad got me wet:
Fit 60-year old wants to pleasure you with his tongue, fingers, and more… I haven’t been with a woman in a long time, and I have a lot of unreleased passion that’s waiting to fill you. This is my first ad, and I hope it’s my last. I’m not looking for a one-night stand. I’m not necessarily looking for a long-term relationship either. I’m looking for someone like me, someone who lives a solitary life and would like to occasionally explore her passion with a clean, attractive man who will leave her satisfied. Please write me a line and let’s see where this goes.
I wrote him that night. I told him my first name, my age, that I hadn’t had an orgasm with a man since my first boyfriend seven years ago. I told him that I wasted way too much time in my second relationship, especially since it wasn’t sexually pleasurable for me. I also explained that this was my first time looking on a website like this. I wanted something clean, safe, and discreet. I took a quick headshot with my webcam and sent the picture file.
He wrote back within an hour. His name was Kevin, and he told me that his wife died a year ago after a long battle with cancer. Kevin wasn’t interested in anything serious, but like me he wanted to explore his physicality with someone. He wanted to meet for dinner tonight and possibly more afterward.
When I opened the attached file, I was happy to see that Kevin’s picture looked almost exactly like I pictured him. He had a head of silver hair, a well-maintained mustache, and a rugged look about him. In the picture he was wearing jeans and a flannel shirt. I couldn’t see much in the way of his chest, but he didn’t look like he had a pot belly like most other guys his age did. I found myself drawn to that telltale bulge in his jeans. I wanted this man.
If I had more time to really think about what was going to happen, I would have likely backed out of the impromptu date. After all, meeting a strange guy that was more than twice my age for sex wasn’t a typical night for me. But it happened so fast. One minute I was lounging around in my pajamas getting wet reading internet personals, and the next minute I was getting a shower and putting on a sexy dress. I hadn’t put on a sexy dress in years.
I took great care in getting ready with a steamy shower. I shaved every hair that wasn’t on my head off my body. I hadn’t had a shaved pussy in years, and I couldn’t get over how thrilling it was to feel the air against me. Even casually bumping up against the footboard of the bed was a titillating experience. I decided to wear a thong with a lacy garter belt. I slid my turquoise dress over my curvy body. I loved how it hugged my generous, full breasts, tiny waist, and gently-curved hips. I expertly applied a minimal amount of makeup, spritzed my favorite perfume on my wrists and behind my ears, and looked at myself in the full-length mirror, applying final touches until I was 100% pleased with the end result.
Kevin and I were to meet at a fancy steakhouse in downtown. I got there about five minutes early, and I nervously waited in the reception area. Every time the front door opened, I held my breath, anticipating the living version of the picture I saw. Each time I became more disappointed when it wasn’t him. Finally, Kevin arrived. He looked even yummier in person. He was wearing a suit with a green tie, which matched his emerald eyes.
He strode right over to me. “Tabitha, you look gorgeous.” He leaned over and gave me a peck on the cheek. The mustache gently tickled my cheek. “You look better in person than I ever anticipated.”
I smiled teasingly, “It was a bad picture, wasn’t it?”
“I couldn’t see your body. Why were you hiding it?” Kevin asked gruffly as we approached the hostess.
“I didn’t want you to come just based on my hot body,” I murmured in his ear.
Kevin’s hand was firmly on the small of my back as we walked through the small restaurant to our table. The restaurant was filled mostly with couples dining intimately at candlelit tables. A few groups were seated at large round tables. I noticed a few men’s eyes linger on me. It was hard to tell if it was because of my looks or because Kevin and I had such a large age discrepancy. It was arousing to think of Kevin as old enough to be my dad. I couldn’t believe how much passion I had at the thought of an older, more experienced man like Kevin touching me, almost like he was a commanding sex coach. Before Kevin, I had only had two boyfriends. One had been nineteen, and my most recent ex was only a year older than me.
I had anticipated being uncomfortable at dinner. What would the two of us talk about? I thought it would be like any other first date, where you talk about what you do (banking) and your interests (watching reality TV…errr long walks on the beach). Surprisingly, we talked about his wife who had died. He expressed how much the two of them were a team and how her slow death broke his heart. I talked about my selfish ex-boyfriend who was keeping me as a placeholder until he found someone he loved. Without the guise of making a great first impression, we didn’t have to keep up false pretenses. And that was insanely refreshing.
When Kevin dropped his fork, he retreated under the long tablecloth that skimmed the floor, and I jolted when I felt a tender hand slide up my leg initially. It kept going further and further up, and soon Kevin’s fingers were touching my naked upper thigh. I felt his warm breath on me, and I parted my legs unconsciously. His manly hand pushed aside my panties, and I quivered with excitement when his tongue gently licked my pussy. His mustache tickled my inner thighs. I could hear him murmur. I wanted to lean back and enjoy the pleasure, but I’d catch the attention of the rest of the restaurant. Instead, I tried to keep my upper body still as my lower body contorted. I couldn’t part my legs that far within the constraints of the fancy armchair. Still, Kevin managed to get his tongue inside me and was tongue fucking me, my pussy walls massaging his tongue just as much as he was massaging them. The under-the-table activities didn’t last long. He gave the outside of my pussy just a few laps and the inside only a few tongue thrusts. I craved more. After all, my pussy hadn’t been licked in half a decade. But here we were in a fancy restaurant, and we had to have a level of decorum.
When Kevin came up, holding his fork, he gave me a sly smile. “Your pussy is amazing. And tight. It’s like you’re still a tight little virgin.”
“Will you teach me tonight?” I said coyly.
He leaned toward me, and I could faintly smell my pussy on his breath. “I want to devour you. My wife was sick for so long. I haven’t had pussy in about four years. It’s just me and my hand every night. I want to fuck that perfect pussy of yours all night long. I want to make you come over and over. You said you never came with your last boyfriend. That will change tonight.”
It was hard to concentrate on eating my meal. It was a huge salad that took forever to eat. Once Kevin finished his steak and baked potato, I forfeited my salad. He offered to get dessert, and I sighed, “I think I’d like a different type of dessert.”
Kevin paid the bill and signed his name on the credit card slip with a flourish. I had resisted the urge to slip under the table like he had done and suck him like a lollipop. I wanted to make him grimace with pleasure.
What was amazing about Kevin was that he kept his cool. Although he said that he wanted me, Kevin remained so confident and in control. Even leading me out of the restaurant, he seemed like he didn’t have a care in the world. It didn’t seem like the meat between his legs wasn’t straining to get out even though I knew it was.
All that changed when we got outside. He whispered in my ear, “I brought my van tonight.”
“I don’t rate a hotel?” I asked.
“You rate the Ritz Carlton, and I got us a room for us there tonight. But I don’t think I’ll be able to make it that long. I want you now. Don’t worry, no one will see us. The windows are tinted. The whole dinner I thought how I want to please you in the back of my van.”
Before I knew it, we were making out as we walked to his van that was in the desolate parking lot. The back of a van was incongruous with the beautiful meal and the Ritz Carlton, and I kind of liked the potential dirtiness of it. I hadn’t ever been taken in a car, and frankly I got even wetter of the thought.
The van was the type with miniblinds on the windows. Inside was impeccably clean with two rows of burgundy cloth bench seats. He had parked the van near a streetlight, and we could see each other through filtered light.
Kevin’s kisses were tender but demanding. I loved his gruff, commanding voice. “Lay down and spread your legs.”
I laid down across the bench seat with one leg up over the back of the seat and the other hanging off the edge . Kevin knelt between my legs. He took off his suit jacket and threw it on the ground, undid his necktie and tossed it next to the jacket. Then he hiked up my dress, displaying my garter belt and pink panties.
“Oh god, I want you,” Kevin breathed. Then he pushed aside my panties and feasted on my pussy. I writhed in excitement as his tongue entered me. I gasped at the intensity, wave after wave of excitement. Within a couple of minutes, I had a full-fledged orgasm, bucking underneath his nimble tongue and letting out a long moan.
Kevin wanted to keep licking me, but I couldn’t handle the intensity. “Give me a second,” I murmured, closing my eyes and enjoying the warmth of the orgasm. He kissed me, and I tasted myself on him.
I unbuttoned his shirt. “How can I pleasure you?” I opened my eyes to see Kevin’s s smooth, broad chest. It looked better than my ex-boyfriend’s chest despite Kevin being more than thirty years his senior. My hands fumbled with Kevin’s pants.
“Suck me,” Kevin uttered.
I unzipped Kevin’s pants to see that he had on a pair of gray boxers. The tell-tale mound under his boxers looked pent-up, like it needed the release that my mouth could give it. I pulled off his boxers and stared at the delicious dick in front of me. Throbbing, dark pink, the skin actually almost like velvet, I anxiously pulled it into my mouth. Kevin’s dick was about the same size as both of my exes’ dicks — about six inches. My exes both claimed that I was incredibly tight, making sex amazing for them despite being an average size. In fact, my most recent ex liked my tight cunt so much that he reliably came within two minutes of fucking me. It’s no wonder why I never had an orgasm with him.
As I went down on Kevin, taking him slowly into my mouth, he gasped. He had been kneeling above me, but now he collapsed on the seat. I changed positions as well, kneeling on the van floor between his knees, sucking him slowly, paying special attention to the spot on the underside of his dick where it met the head. I’d do a few sucks down the length of his penis, as far as I could go, and then I’d lick that spot back and forth. I was driving him crazy based on his thrusts, moans, and salty pre-cum.
Kevin pulled his dick out of my mouth. “I love this, but I’ve been thinking about fucking you all night long. Can I?”
I could feel my juices getting ready. “Please. I’m not on the pill though.”
“I had a vasectomy years ago. And I’ve only slept with my wife.”
I gave his dick one last lick, “How do you want me?”
“On your hands and knees on the seat,” Kevin got up, his dick glistening with my saliva in the streetlight.
I got into position, tilting my hips to give him complete access to my incredibly sensitive, ready pussy. “I’ve never done it doggy style,” I stated.
“Neither have I. I’ve always wanted to,” Kevin took the opportunity to give my pussy a few licks from behind. Just as I got used to the feel of his tongue, he backed off and soon after I felt his hands on either side of my hips and his dick slowly entered me. I turned around to see Kevin’s eyes closed and his mouth slack-jawed as he kept entering me. God, he felt huge in my hole that hadn’t been stretched in months. I wasn’t sure I could fit him; he still wasn’t completely in. He started thrusting slowly, and I met each thrust. Soon he was entirely in, as I could feel his pelvis against me, smacking into me with each thrust as his thrusting became increasingly frantic.
His hand reached around me and started rubbing my pussy. The stimulation was just too much. He was completely filling me on the inside and rubbing my clit on the outside. And he was grunting above me, “Your pussy, god, your pussy.”
And that’s when I came again. Unlike the other time when it was a warm waves of pleasure, this orgasm was piercingly intense, and I shrieked. Loudly. I had never come with a dick in me before, and I had never been that loud. Kevin took his hand off my clit and clenched my ass and hips with both of his hands. He was riding me with such intensity that I knew he was going to fill me soon.
Kevin’s grunts as he came were absolutely primal. He jerked and bucked as he came, and it felt like he continually emptied into me for at least a minute. He slumped on top of me; I could feel the sweat on his chest. He uttered, “This is gonna be messy.”
He pulled out, and the dam had broken. It felt like torrents of jizz streamed out of me. “A guy should always clean up his mess,” Kevin uttered, and then he gave me small kisses as he proceeded to move down between my legs. Cum was on my thighs, and he lapped it up. Never before had I seen a man eat his own cum off me with such fervor. After he cleaned off my thighs, he started licking the outside of my pussy. I became putty in his hands as he turned me over, laid me down on the seat, and went to town. I soon had my third orgasm of the night.
I reached toward Kevin’s dick, “I want you in me again.”
He quietly replied, “We have all night. Let’s take this one slower. How about we continue this at the Ritz?”
When I realized that he still hadn’t seen my breasts, which were still firmly in the bra and dress, I realized that Kevin was right. We had all night to continue to explore each other.