The Blind Date

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Mar 18, 2023 // By:analsex // No Comment

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A few decades ago I spent the summer after my second year of college working in Hartford. It was a mundane computer programming job at one of the large insurance companies – not very challenging, but it allowed me to focus on what is important to most every 20-year-old male: getting laid and getting drunk – and in that order, at least for me.

When I got to town, I looked through the want-ads and found a room to rent – a spacious room on the top floor of a three-story Victorian in an old neighborhood on the west side of the city. During the school year most of the rooms were occupied by college students, though those guys had left for the summer by the time I arrived, so my housemates in this partially filled house were twenty-somethings with fulltime jobs. One was a carpenter, another a phone company technician, and another sold commercial air conditioning.

A benefit to having housemates in a new town is tapping into their existing network of contacts. My first blind date was a double-date with my phone company housemate, Jim. One of the girls he dated (“dated”, as in they’d hang out at a bar for awhile, and then he’d bring her back to his room to fuck) had a girlfriend who reportedly “wasn’t seeing anyone” and was looking for “some casual fun.” That seemed promising to me.

It was a Wednesday night. I drove Jim to a local bar a mile from the house. Gillian (his date) and the friend were already there, sitting side by side in a booth. Jim introduced me to Gillian, whom I’d never formally met, even though I’d heard her laughter and her orgasms as I’d walk past Jim’s bedroom door on my way to the bathroom. Gillian introduced Annie to me. I slid into the open side of the booth, and Annie moved across to sit next to me, and Jim sat down next to Gillian.

Whereas Gillian was tall – like Jim – and skinny, with long blonde hair, blue eyes, and exuding a “Look at me, I’m so pretty!” attitude, her friend Annie was barely five feet tall, with pixie-short black hair, dark eyes, full lips, and a curvy body. Even better, she gave off an approachable, friendly, laid-back vibe.

The girls had been drinking beer. Jim ordered another pitcher and a pizza. When those were gone, Jim and the girls began downing tequila shots. I passed on the shots, otherwise I would have been staggering home on foot. By then the girls were pretty sloshed, Jim was feeling no pain, and I was riding a minor buzz. Gillian had her head on Jim’s shoulder. “So,” she said across the table, looking directly at Annie, “Should we go back to my place for awhile?”

I looked at Annie. She looked at me, then back to Gillian. “Okay.”

We all piled into my car. As it turned out, Gillian lived just a few blocks from the bar, Annie’s brother had dropped her off at Gillian’s house, and the two girls had walked to the bar to meet us. Gillian lived in a small house that she shared with a female roommate who wasn’t planning to be there that evening. They each had a bedroom and shared a single bathroom. The living room had a couch and some other worn-out assorted furniture.

Annie and I went to the kitchen to look for something to drink – cheap beer and Diet Rite cola were the only choices – and when we returned to the living room, Jim and Gillian were pawing each büyükçekmece escort other on the couch. Gillian disentangled herself and stood up, wobbly, and pulled Jim by the hand toward one of the bedrooms. “Make yourself at home,” she mumbled with a slurred voice over her shoulder. Her bedroom door closed with a thump.

Annie sat down on the couch. I sat next to her, wondering what the next step was. Annie leaned toward me, tilted her head, and gave me the silent go-ahead to kiss her. Which, of course, I did. Her mouth tasted of beer and tequila and breath mints. Her body sank against mine, and our mouths remained mostly connected as we slipped into a horizontal position. She squirmed, I squirmed, and before long she was on her back, pressed into the cushions, and I was lying on top of her with an erection that had to be as obvious to her as it was to me.

We were both breathy, with busy tongues and bodies pressed together. My mouth alternated between her lips and her neck, and her fingers alternated between sluicing through my hair and digging clawmarks into my back inside my pulled-up shirt. I edged my body southward, raising up her tanktop to expose her bra. The front clasp was soon undone, and my mouth on her handfuls of boobs and my teeth teasing her fully stiff dark nipples were met with her little whimpers and moans.

Continuing southward, I kissed a straight line down the middle to her belly button, then met the waistband of her shorts. No sooner did my hands get to her waistband when Annie’s back arched and her hips lifted. It was a clear signal to pull those shorts down, and down they came, shorts and panties, across her hips, past her knees, and deposited on the floor.

And then my face settled in between her thighs, and I got acquainted with a nice thicket of soft, curly pubic hair and a set of pussylips that were pouting and ready for action. Annie had a musky scent that hardened me another notch, and I dove in. She had delightfully suckable lips, fatten by her arousal and yawning wide, with a stiff clit at the top and juices that flowed like a spring creek. My tongue grazed up and down, in and out, side to side. Faster, slower, faster. Annie’s legs yawned wide and she panted and gasped and grunted and squirmed. Her fragrant juices smeared across the lower half of my face. I was in heaven!

Did she want to come this way? Was she willing to fuck? My mouth slowed. I waited for a signal.

She gave it. Annie tugged on me, and I moved higher, looming above her. Her hands cradled my face and we kissed. She must have tasted her juices on my mouth. “Do you have a rubber?” she asked. No. “Damn.” Hesitation. She was thinking, calculating. “Let me suck you.”

That seemed like a decent compromise. We fumbled in a tipsy haze into new positions on the couch, this time with me on the bottom and Annie tucked in between my legs, hovering her face over my rigid cock. She gripped a thumb and forefinger around the base, and then slipped her lips around my cockhead and circled the rim with her tongue. Needless to say, that got my attention. My moan elicited one from her, too, and that vibrated around my cockhead in a way that produced more moans fatih escort from deep in my throat.

My previous girlfriends had all been hesitant, at best, about giving me oral sex. They were all happy to receive it, just reluctant to reciprocate. Maybe it was due to a fear that I might ejaculate into their mouth? Or was it a shyness about spreading their legs and exposing their most intimate body parts to me? In reality, I didn’t climax from oral sex back in those days. Maybe that was due to my own fear of upsetting the girl whose reluctant mouth was busy pleasuring me, or maybe it was due to a lack of skill on the girl’s part and my inability to verbalize helpful suggestions.

Regardless of the reasons, the outcome was still the same. Despite Annie’s best efforts, which seemed to me to be well practiced, I was stuck at a plateau. She disengaged her mouth and looked up at me, slowly jacking my very hard, very slick shaft. “You can cum in my mouth, you know.”

“I wish I had a rubber.”

Annie seemed to ponder my statement for a moment. She gave my cock a couple of long, upward licks with the flat of her tongue. Then she paused again, raised herself up on her knees and outstretched arms, and squirmed her body upward until she straddled my hips. My cock made contact with her pussy, and I began a teasing stroke up and down her cleft. “Don’t you come now,” she scolded me. Yeah, right, I thought.

We got into that primal rhythm. I asked when she expected her next period. “In a few days,” she said. I told her it was probably safe. “Yeah,” she replied, and closed her eyes. Up and down, my cockhead plowed a furrow from the heat of her vaginal opening to the knobby bump of her clit, up and down, wetter and wetter, her pants and gasps ever increasing, her hands on her knees, her hips doing a slight little rocking to match my longer strokes.

On one of those strokes I accidently-on-purpose I dipped my cockhead just inside the snug ring of her opening, and she inhaled a gasp, then when I continued the upward slide between her lips, she exhaled a long “Ohhhhh.” Three strokes later I tried it again, with the same result. Then two strokes. Then I lingered there, her vagina tweaking little clenches just below my cockhead.

“Okay?” I asked, and she breathed a beery “Okay” in response. And inward I slid. I granted myself a slow torture, one fraction of an inch after another, sinking deeper and deeper into what I still remember today as one of the snuggest, slickest, hottest snatches I’ve ever encountered, before or since. Annie began to pant, her hips rocked faster, but I resisted – Lord knows I wanted to – an intense desire to just stab into her with one powerful, bottoming-out thrust.

And when I did finally bottom out, I truly bottomed out. My pubic bone mashed against hers and I felt her slick, warm walls embracing my entire shaft. This, I told myself, this was going to make me explode. Her vagina was alive, giving me those little clenches, while her body was doing those gyrations around the root of my cock, her weight pressing me back against the couch cushions, her mouth trying to maintain an open-mouth kiss while also fighting to breathe her gaspy pants.

“Oh esenyurt escort fuck,” she breathed, and I did. Mostly my cock stayed embedded, with my hips rocking a rhythm of pressures against her inflamed pussylips and clit. Four, five, six of those, then I’d draw my cock back most of the way and sharply thrust back in and do the pressures again. Whatever I was doing was working for Annie, which was a good thing because I knew I wasn’t going to last very long myself. Here we go, I thought to myself, and I picked up the pace. It was the same steady rhythm, but ever so slightly faster and faster.

I got there first. That old primal instinct overwhelmed any remaining self-control I pretended to have, and I gave her a few final, wet, slickery pumps. My cock stiffened into a steel-pole hardness, and I lunged upward to bury myself again in her juicy snatch and unloaded. The first intense spasm exploded my skull. I think I cried out something as I released that first long spurt. My heels dug into the soft couch cushion and I tried to raise my hips to push in deeper. Annie’s face scrunched up and she began to hyperventilate. My second spurt triggered her orgasm. She popped with a high-pitched squeaky squeal, holding her breath, her back arched and her hips pressed down and the rubbery tip of her cervix quivering against my cockhead.

Pulse after exquisite pulse, I squirmed against her nether grasp, stretching her vagina at different angles with my shaft, emptying my balls into her sweet embrace. I managed to restart my strokes and felt her liquefied sheath. “Oh God oh fuck oh God oh fuck,” she moaned as I filled her. When I was done, Annie was still quivering with little shudders, as we both struggled for oxygen. When my erection finally softened, Annie lifted her hips and my cock reluctantly slipped out. Annie reached a hand to her crotch. “Shit,” she murmured, “What a mess.”

I sat up. Annie swung her legs around, keeping her hand cupped between her legs. She stood up, picked up her shorts and panties from the floor, and walked unsteadily to the bathroom. It seemed like a good time to pull my pants back on. She emerged from the bathroom wearing her shorts and made her way back to the couch, plopping down heavily, head tilted back and eyes closed.

“Are you okay?” I asked.

“A little dizzy.”

I gave her a moment to settle herself. Finally, she opened her eyes and looked at me. “I kind of have a boyfriend.”

“Oh. Okay.”

Annie returned to her slouching position. Her eyes closed again. “I shouldn’t be fucking you,” she said.

“I understand. I just – I mean, I enjoyed meeting you. I enjoyed tonight.”

“Me too.” Annie sighed, then slumped toward me. We ended up mostly horizontal again, kissing. She whispered in my ear, “I loved feeling you cum.” She playfully nipped on my earlobe. “And feeling all gushy inside.”

“And I loved being inside you. And making you gushy.”

Annie giggled. “I have a confession to make.”


“I have a condom in my purse.”

“So why didn’t you…”

“I wanted to feel you. Without it.”

The bedroom door opened, and Gillian and Jim walked out. Annie and I sat up. There was a few moments of awkwardness, then Jim and I said our goodbyes and we left.

The next week, Jim poked his head into my bedroom. “Gillian called me. She said that Annie said to tell you that everything worked out on schedule. Whatever that means.”

“Ok, good. Tell her thanks. I never got Annie’s phone number.”

“She has a boyfriend, apparently.”

“So she told me.” I wondered if she used that condom with him.

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