The First Date [Cale & Bev] [Prostate play]

Author’s note: this is complete fiction. I intend this to be an ongoing series about a new relationship between a heterosexual man and woman and will be erotic in nature. The series will include oral, anal, prostate massage and pegging.

I’m trying to paint a picture and tell a story. Constructive criticism and suggestions are very welcome.
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Bev and I had known each other for over a decade. We knew each other throughout our marriages and watched each other’s fall apart. Both had ended at about the same time a year prior. Neither of us had darted since and really had no desire to as we both exited a toxic relationship.

Bev is a strikingly attractive woman. At 5’4” she weighs about 130 pounds with curves in all the right places. Her brilliant red hair is to the middle of her back and has a nice wave to it. She has a wonderful hourglass figure and ample C cup breasts.

I (Cale) am 6’ tall and 190 pounds with an athletic build. My hair is salt and pepper and clean cut. My beard is cropped very short.

We ran into each other at a coffee shop on a Friday morning before work. After a quick greeting we sat down and caught up. We exchanged details of our healing paths and where our lives were headed. We quickly learned we shared a lot in common. Some of our interests crossed like hiking and camping and the outdoors in general. She also shared my interest in emerging technology and motor sports. She had even raced herself years ago and thought about getting back into the competition. What a turn on for me.

We clicked so well that I took the plunge and asked her if she was free for dinner that evening. She accepted the invite and we went our separate ways to work.

I didn’t get much done that day. I was nervous and excited. I had butterflies for the first time since long before I was married. I didn’t even feel this on the first date with my ex wife. It was exhilarating.

The day ended and I made my commute home. I freshened up with a shower and quick grooming session and dressed in a more casual jeans, casual button down and a pair of my cowboy boots.

I decided to grab an Uber to the restaurant since I figured I’d probably have a coupe of drinks to unwind. When I arrived at the restaurant our table was not ready which was probably a good thing since Bev was not there yet. I took a seat at the bar where I could watch the door and ordered a smoked old fashioned, a cocktail this establishment was famous for.

A few minutes after my drink arrived, Bev walked through the doorway into the bar. My god she looked good. She was wearing a classy red and white striped blouse that hugged her breasts tightly, a black pencil skirt to her knees that was form fitting and accentuated her luscious hips, no stockings to reveal her smooth tanned and toned legs and a pair of closed red pumps that showed how muscular her calves were. I felt a stirring I had not felt in a long time.

I rose from my seat as she approached. She leaned in for a tight hug. She smelled so good. As her hands pressed the small of my back, pulling me tightly into her I could feel myself becoming aroused.

“Down boy,” I thought to myself.

“Wow, you look stunning tonight,” I said out loud.

“As opposed to what I usually look like?” Bev mused.

We shared a chuckle and she sat beside me at the bar and ordered a dirty martini.

Our conversation picked up where it left off in the morning. We had a few laughs. I could not help glancing at her cleavage occasionally but always made sure to bounce back quickly to her lovely green eyes. I’m sure she caught me a few times.

At one point she adjusted in her bar stool and crossed her legs. Her calf landed against mine. She was in the middle of a sentence and she touched my forearm and slowly smoothed her palm down my shirt sleeve to my bare hand. When our skin met it was like electricity danced between us and our eyes locked. Hers seemed to sparkle like diamonds in the sunshine. She must have felt it too because she stopped mid sentence for a few moments before shaking her head, looking away and up and continuing with what she was saying. Once again I could feel my pudge swelling in my shorts.

The conversation was steady. When I said something funny she would sometimes throw her head back in laughter and touch my knee. It had been a long time but her signals were obvious. She was as into me as I was to her. Was I ready for sex yet? My cock was certainly saying yes.

We ordered another round and shortly after the maitre d’ fetched us to bring us to our table. I walked behind her and could not resist watching her ass and hips sway. He slid Bev’s chair back and as she sat, I got a view straight down her blouse. Her tits were magnificent.

“You should see them naked,” Bev whispered across the table.

“I’m so sorry. It’s been so long and I…”

She started laughing.

“I don’t mind one bit. I enjoy the attention and am flattered you’ve been glancing at them all night,” Bev responded between chuckles.

“You can’t blame a man for glancing, but I don’t mean to be disrespectful.”

“No disrespect was taken. I’m glad you like them. But I need to warn you that I don’t put out on the first date.”

“Point taken. I was just hoping for a good night kiss.”

Bev’s face turned a deep shade of red and she bit her lip. A slight smile parted her lips and she looked down.

“We will see how the rest of the night goes,” she replied.

We shared an order of oysters and a wedge salad. I had surf and turf she had the salmon. And we split a bottle of wine.

Our conversation was good and flowed easily. It was as if we had known each other our entire lives. A few innuendoes peppered our conversation. I loved the flirting and must say I was smitten with her. Not just her looks. She was smart, she was funny, she had a rapier wit, would occasionally tease me over something silly… that plus her looks… I was hooked.

We ordered a lime cake to share and each had an Irish coffee. I couldn’t wait to ask her out again.

“What are you doing Sunday? Are you interested in some Top Golf and some afternoon cocktails?”

“We are not even through with date one and you’re already asking for a second?” She replied with a musing smile.

“Well I had to see if I was on track for a kiss before I picked up the bill.”

She erupted into laughter.

“You’ll get your kiss and Top Golf sounds fun, so sure,” she said through a breathless smile. “I’m going to go powder my nose.”

I gave her entire body a once over as she walked to the restroom. God she was hot. I felt my cock becoming erect. I was like a teenager again. I could not control it.

She got my same gaze as she walked back to the table, her hips and chest swaying with her gate.

She came to my side of the table, bent down and whispered in my ear, “Did you miss the view?” and kissed my cheek.

The butterflies in my stomach were fluttering and a chill raced up my spine from her breath on my ear. I’d not had a woman’s lips on me at all in years. My marriage had been a dead bedroom for the last 5 years we were together. The last 2 years my ex had moved into another room. Bev’s touch was electric and intoxicating. I was so hard my shaft ached. It physically ached. I was not leaving the table for a bit.

“Do you want one more coffee?” I asked. I really hoped she did because I was going to have to sit at this table until my raging erection was gone. I needed to get that blood into my other head.

“Mmmmmm… one more then I really should get home,” she relied.

When the waiter came over I asked for two more Irish coffees and the check.

I made sure to avoid sexual conversation. I asked about her favorite places to hike and camp, about her racing and other such things. I finalized the bill and the only remnant of my earlier arousal was a small wet spot of precum I could feel in my shorts.

I held her hand as we walked out the door. The flesh of her palm was so soft. We chatted outside the restaurant for a few minutes.

“Where do you live,” I asked.

“Three blocks away. Just past Canal Street.”

“Oh wow, can I walk you home? I can catch my Uber from there.”

“I’ve had worse offers,” she laughed as she took my hand and started walking towards her home.

We turned what should have been a 15 minute walk into 45. We talked about anything and it was easy.

“Well this is me,” she said when we arrived at her door.

We stood there for a few minutes, eyes locked. I was breathless. It seemed she was too and she had a nervous grin. I finally leaned in and kissed her. My shaft was instantly erect again. Stupid cock. I held my body away from hers in an attempt to try to conceal it. I had my hands in the small of her back just at the curve of her ass. Her hands were on my hips. She pulled me in closer to her and I felt my erection press snugly against her. I was so hard. I’m sure she could feel it. Our tongues entwined in a slow methodical dance. She tasted sweet and I could feel her breathlessness. She grinded herself more tightly against me, pulling me more into her. I thought I could cum just from that.

We finally withdrew. I cupped her cheek in my palm. “What a wonderful end to a wonderful evening, Bev,” I whispered as I gazed into her eyes. “See you Sunday?”

“Do you want to come in?”

“I thought you said…”

“I did. And I meant it. I’ve never been this forward on a first date but you… I just feel like I’ve clicked with you… and I feel safe with you… and I’m so fucking horny right now… And I know you are.” She gave my cock a little pet through my jeans. It leapt and we both erupted into laughter.

“Bev, I’d love to come inside, but I don’t want you to regret it. And I’m probably going to be a lousy lover, it’s been so long and I don’t want to lose our second date on Sunday…”

“Don’t worry about that. I’ll give you a second chance unless your really bad.”

We both chuckled again as she took my hand and led me through the door.

Once inside, we were making out like a couple of high school kids. I ran my hands down her back and finally gripped her firm ass. She definitely had a hard body. I nuzzled into the nape of her neck and kissed where it met her shoulder. She pressed into me so firmly I could feel her breasts against my body.

She led me to the couch where we continued our petting. I untucked her blouse from her skirt and my palm made contact with her smooth skin. I was again so hard I was aching. I felt like if I just ground into her for a few seconds it would be over. And I didn’t want it to be over. I continued running my had up her belly and past her ribs and finally grasped one of her firm breasts. I could feel her hard nipple through her bra. She pushed me back a little and removed her blouse and bra, grabbed my head and guided me to her nipple. I took it in my mouth and my tongue swirled circles around it. I kissed across her chest to her other breast and gave it the same attention. One of my hands was running up her inner thigh. She again pushed me back and slowly unbuttoned my shirt revealing my chest and then slid my sleeves down, my shirt falling to the floor.

She kissed each of my nipples before taking on in her mouth and sucking it hard. Just before she stopped she gave it a gentle bite.

She pulled me into her again, gripping my back as we kissed. Her skirt bunched up around her wasted and I was grinding my erection into her groin. I could feel her soft flesh against mine, her firm, natural, naked breasts pressed into my chest. Our tongues were dancing again, but this time more urgently.

She pushed me back again.

She stared into my eyes. I could see the tension. I could see her lust.

“Come with me,” she said, taking my hand.

She led me to her bedroom and pulled back the covers.

“Get in. I’ll be right back,” she said as she hurried into the bathroom.

I hastily kicked my boots off and slid my jeans and boxer briefs off. My cock was so hard that it was standing upright. It had not done that in years.

I lay down in the bed and glanced at the bathroom door and she was standing in the threshold, completely nude with the exception of her red pumps. Her body was completely hairless below her eyebrows with the exception of a small, narrow tuft just above her slit, revealing that she was indeed a natural redhead.

“My god, you are beautiful.”

She slowly walked over to the bed, her hips swaying. I could not believe how arousing this was. When she got to the bed, she pulled the covers off of me, revealing my erection. She kissed me again as she took my shaft in her hand.

“Mmmm… your shaved smooth. I like that,” she cooed before kissing me again, while gently stroking me.

She swung her leg over me and got on top. She straightened her upper body upright and guided my cock to her entrance. With one slow, fluid movement, she slid me all the way into her. A gasping sigh escaped her lips as she pushed her clit into my pubic mound. I could feel the roughness of her pubic hair against my shaved groin as she started grinding her clit harder. The smooth coolness of her pumps rest against my thighs. I ran my hands down her back to her ass, gripping it tightly as she flexed it between grinds. I sat up in bed and took one of her nipples into my mouth again. She gripped my hair with one hand pulling my mouth more tightly against her and caressed my back with the other.

After a few minutes, she began humping me faster. She was tight and I was so afraid I was not going to last long enough for her. I pushed her over on her back and mounted her. My head slid easily into her tight lips again. Her hands ran down my back and pulled at my ass, urging me faster. Her hips rose off the bed, meeting my thrusts.

After several moments I started getting that feeling… I was not going to last much longer…

I withdrew from her in effort to keep from cumming. She initially let out a disgruntled sigh until I started kissing my way down her body. When I got to her mound she said, “Oh god, yes. Suck my clit…”

She grabbed a handful of my hair and pulled me into her. My lips closed around her clit and gently sucked it out of it’s protective hood. She moaned as my tongue began to writhe circles around it. Her juice was sweet and smelled fresh and good.

I ran my hands up her belly again and they found her nipples, gently, yet firmly squeezing them and gently pinching her nipples. I brought one hand back down and slid a finger, then a second inside of her, searching for her g-spot. She was sopping wet.

She began to grid harder and faster into my mouth. She was getting more vocal. She was getting close.

Finally I felt her insides tremble. She held her breath for a moment and lie completely still, but seemingly flexing every muscle she had. All of a sudden, she relaxed but started thrusting her hips again. She moaned as torrents of contractions gripped my finger and her clit pulsed in my mouth. She was cumming. From what I could tell she was cumming hard. I continued at it for several more moments until she couldn’t take it anymore. She was too sensitive from her climax. She pushed on my forehead signaling me to stop.

I climbed up beside her, cupping her cheek in my palm and giving her a long, slow, lingering kiss.

“Mmmmm…. my juice tastes good on your lips…” she cooed.

She caught her breath for a few minutes before sliding her hand down my belly to my still raging hard cock. She gripped it firmly and said, “Your turn.”

She released my cock from her grip and kissed her way down my body. She positioned herself between my legs. She kissed one of my inner thighs, then the other, then proceeded to glide her tongue up my thigh to my balls. She gently took one in her mouth, gently sucking it, then the other. I felt them tighten.

Painfully slowly, she glided her tongue up my shaft to the head. Her tongue flickered across the head before she opened her mouth and engulfed me.

Her suction was amazing. I could not recall a blowjob ever feeling this good. She cupped my balls in her hand, the other wandering my belly and occasionally raking her nails down my flesh.

One of her fingers began pressing on my anus.

“Um… what’s that?”

She let my cock fall from her mouth.

“Have you ever had your prostate stimulated?” she asked in a sultry voice.

“Uh, no. I’m not gay.”

“It’s not gay, silly. It’s a pleasure point. Let me try for you?”

“Hmmmm…”

“Let me try. If you hate it I’ll stop. I think you might be surprised at how it feels. I’ve never had anyone stop me.”

“And how many has that been,” I playfully asked.

“Only a few,” she laughed.

She fetched a bottle of lube from her nightstand. She liberally lubed a finger and started to rub it against my anus. I have to admit, I’d never had a girl touch me there and it felt really nice. It was a turn on.

Her pressure began to increase and I felt her finger slowly starting to enter me. That was not unpleasant either, but we were at the first ring and had the second tighter ring to get past. I’d had anal sex with a few partners in the past, including my ex wife who did enjoy it. I knew the second, tighter ring is where I’d always been stopped in failed attempts. But this was a finger, not my cock. I was still a bit tense and nervous.

“You need to relax,” she whispered, her other hand gently massaging my hip.

I felt her pressure increase again and my inner ring began to yield to the invading digit. It did not feel bad. Odd, but not bad, and it provided a nice, full sensation.

She began gently gliding her finger in and out of me. Then she began to move it a different way. My legs jumped.

“Oh… there it is,” Bev laughed.

I was not sure what I was feeling, but it was good. It was a foreign and odd sensation, but very pleasurable. I could feel her thumb pressing against my taint firmly, almost using it as a hinge, adding an even fuller sensation.

“Close your eyes and relax. Try to focus on the sensation inside.”

She placed her other hand at the base of my cock again, raising it up , and she took me in her mouth again. It was difficult to know which stimulation was feeling better at that moment. She slowed her finger in my ass and then I felt her pushing a second in.

“Oh god… Oh… Oh…” was about all I could manage as the second finger entered me.

With two fingers it seemed to provide more pressure on the pleasure spot. It was beginning to tingle.

She stopped sucking my cock again. I felt pleasure waves building inside of me. It was a completely different sensation. It was very strong.

After a few minutes I started feeling like I needed to piss.

“I need to go to the bathroom.”

“No you don’t. That means you’re getting close,” she responded in a sultry voice.

She put me back in her mouth again and after just a few minutes I started feeling like I was going to cum. She seemed to recognize it and withdrew her mouth from my cock again. She kept working her fingers inside of me faster and providing more pressure on my prostate. The “urination feeling” became so strong that I was afraid I was going to piss in her bed.

All of a sudden the urge to piss left and I felt myself enter the feeling you always get right before you cum. That super pleasurable and intense feeling right before you release where you could not stop your orgasm even if you wanted to or tried. And I just stayed there for what seemed like an eternity. It was at least five minutes, maybe longer.

Her fingers continued to work inside of me. They picked up speed and intensity again and were applying even more pressure it seemed. I felt a twitch.

Waves of pleasure began to crash into me. It’s almost as if pleasure was radiating from the pit of my stomach and all the way through my body. That feeling of being on the edge of orgasm stayed, but I was cumming. I felt my ass gripping her fingers, but it was not normal contractions. I was cumming in a different way, from the inside… I could not believe how good it felt.

Cum started spilling from my cock. It was not a normal ejaculation… more of a flow than a squirt. Bev giggled a little and cooed and oooed. My climax seemed to be lasting forever. It was by far the strongest one I’d ever had and I just kept cumming without any stimulation of my cock. More cum came out of me then I ever remember seeing. I just kept having mini contractions as the waves of pleasure passed through me.

I finally started to subside and Bev took me back into her mouth. It was like I started cumming all over again just as strong but from inside and from my cock. The only way I can possibly describe it is as if I was having an internal and external orgasm at the same time. I would imagine it’s akin to what a woman feels when she has a clitoral and g-spot orgasm simultaneously. My cock spasmed and leapt in her mouth, her fingers still stroking inside of me, her thumb still applying deep pressure to my taint. If I had thought the last orgasm was strong… this was stronger. But it did not last near as long.

The waves of pleasure finally began to subside. I was spent. I literally could not move or talk. Bev stroked me a bit longer with her mouth. It was excruciating but phenomenally pleasurable at the same time. She let me fall from her mouth again but continued to caress my prostate, kissing my hips. It seemed to be keeping me in the “still cumming” feeling for a few minutes longer.

She finally slowly withdrew her fingers from my ass. She got a warm, moist towel and gently cleaned the cum from me before laying back down next to me, caressing my chest and belly.

“I think he liked it,” she whispered in my ear.

“I know he liked it,” I could barely manage.

She cuddled up next to me and I wrapped my arm around her. I fell asleep with her wrapped around me. I don’t think I had ever slept as good as I did that night previously in my life. It was a whole new sensation. Bev had opened a new world to me. I hoped we would get to explore it again sometime soon…

Source: reddit.com/r/eroticliterature/comments/vgzoxt/the_first_date_cale_bev_prostate_play