My First Virgin! by cucumberman

My First Virgin! by cucumberman

Discover an intimate and captivating tale in "My First Virgin!" Explore the complexities of desire, romance, and self-discovery in this adult sex story. Join the journey of love and passion today!<br/> This is Story # 39 of my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own.

Not everyone likes me or my stories. That’s OK. My style isn’t everyone’s cup of tea.

I enjoy all comments.

_____________________________________

Taylor

If you read the “Coaching a College Grad” series, you might recall that Ally had a couple friends from home that I had known as long as I had known Ally, and at a picnic one year soon after I started fucking her, Ally’s friend Taylor gave me some knowing looks, even biting her lip as she looked at me. I had a feeling Ally had told her what we had been up to.

While Ally was MY slut, Taylor was a legit slut, and she looked the part. Her young tits always spilling out; tight, ripped jeans or shorts that showed the outline of her vagina. She was unofficially the town slut.

Or so I thought.

I was out at a local bar one Friday night, two years after Ally moved away, watching a game with a friend. He could only stay for a bit, but I hung back, no other plans.

Taylor was waitressing, trying to make some extra money while she pursued a master’s degree in mathematics. She was really smart, personable, just enjoyable to be around. She was Ally’s age, 24 now. I was 50 – more than twice her age.

Taylor waved to me several times as she would walk by me at the bar, stopping once to say hello. Around 9:30 I saw her come out of the back dressed in regular clothes, her shift over for the night.

She plopped on the empty stool next to me and said, “Buy your girlfriend’s friend a drink?”

I laughed and responded, “Not sure what you mean, I don’t have a girlfriend.”

“It’s OK,” she said. “Ally told me, but I’m the only one she told. Your secret is safe with me.”

“Do you realize how dead I would be if this got out, and got back to her dad. Deader than dead.” I warned. “So please, don’t tell a soul, OK?”

“What’s it worth to you?” she asked.

Was this little bitch blackmailing me? I was getting pissed, and worried.

“Let me ask you, what’s it worth to YOU?”

“Well played,” she laughed. “Seriously though, I was wondering, would you be willing to, you know, help me the same way you helped her?”

I was shocked. Of anyone who I would have guess needed a sex education, it wouldn’t have been Taylor.

“No offense Taylor, but from what I understand, you’ve had your fair share of boyfriends over the years. I’ve seen lots of pictures on social media of you with plenty of guys, so I guess I’m a little confused.”

“Yeah, I know,” she said. “Everyone thinks I’m a slut. I dress slutty and I’m always with guys. Truth is, I’m more of a tease than a slut. I’ve kissed a ton of guys, and had my tits played with and pussy fingered, and given a few hand jobs, but that’s it. I’d always get scared to go further than that.”

“But you wouldn’t be scared with me?? I’m 25 years older than you.”

“I guess that’s the point. Guys my age are so anxious to just stick it in you, you know? Ally said you really take your time and there’s no stress or pressure.”

“So, are you saying, you’re a virgin?”

“Yep, go figure. A 24-year-old virgin, made it through college with my cherry. As a math nerd, I’d say – what are the odds of that?”

This was interesting. i had never taken a cherry. And now, an opportunity to deflower a 24-year-old.

I considered the risks. She was more than legal of course. Her family, which I barely knew, had moved away, so there was little risk of her father shot gunning me. There was little reason to reject this beauty. Still, I gave her one more chance to change her mind.

I replied, “Shouldn’t you just save yourself for marriage at this point, or at least someone you love?”

Taylor rolled her eyes.

“Seriously?” she said. “What is this, 1950? How many people do you know that are virgins when they get married? Plus, I want to know what I’m doing. I don’t want to meet a guy with experience and I’m clueless. And it’s not like I have a boyfriend at the moment and am gonna fuck around on him like Ally the Ho!”

I laughed, “Ouch!” I said. “Low blow!”

“So, what do you think?” she followed up. “Are you afraid I’ll be too much for you?”

She stood as she said this and ran her hand down her body.

This was funny because Taylor was little more than a pixie, standing I’d guess no more than five feet tall. She couldn’t have weighed more than 100 pounds, probably less. She had to give up all of her sports in high school because she was just too small.

I stood as well, a good foot and a half taller than her, and looked her in the eyes, a serious look on my face, and said, “If we do this, we’re goin’ all the way. I won’t be teased. I’m not into having my time wasted. And we’ll do it my way. You got that?”

I saw her shiver a bit, maybe more of a tremble, and she looked up at me and said very quietly, “I understand.”

She asked for my number, then texted me her address.

“I work a day shift tomorrow. Can you be there at eight tomorrow night?” she asked.

“Sure thing, see you then.”

I threw money on the bar and turned to leave. She grabbed my arm and turned me back to her, pulling me down and getting up on her tippy toes, barely reaching me to give me a peck on the cheek.

“Thank you,” she whispered.

“Thank me tomorrow,” I said, and I left her.

*****************

Taylor’s parents had moved to Arizona upon her college graduation, so she was living on her own in a small townhouse they were renting for her. Very cute and quaint in a little suburb near our town.

I tapped on the door and heard Taylor yell for me to come in. She was in the kitchen in a tight pair of jean shorts and a crop top that barely covered her tits, but nothing else. Her flat stomach and tiny waist were on full display. She was just so damn little. She handed me a glass.

“Ally said you like bourbon,” she said as she handed me a glass full.

“I do, thanks,” I answered, and grabbed a seat.

I took a sip and looked at her.

“What else did she tell you?”

I could tell she was nervous, and why wouldn’t she be. It was all fun and flirty in the bar the night before, but here I was in her kitchen, alone with her, having been invited over to take her virginity. But she was a very confident person so she was carrying the nerves well.

“Honestly? She said you are an amazing kisser, you have a magic tongue and a huge cock and know how to use it, and you come like a fire hose. Oh, and she said I’ll be walking funny for a week.”

“Oh?” I said, surprised. “So, you told her that this was happening?”

“I didn’t have to, it was her idea!”

I guess that explains the random text from Ally earlier that day saying – thinking of you, hope you have a great day!

Taylor continued, “She said she wishes she was here so she could watch.”

Oh, she’d do more than watch, I thought to myself.

Taylor walked over to me and leaned down to kiss me, opening her mouth and offering me her young tongue. We kissed for a good minute, and I could feel her squirming and hear her moaning as our kiss progressed. She sat down on my lap, giving my hand more access to her tiny body.

“I outweigh you by more than 100 pounds I’ll bet.” I said to her.

“I’m 4’10”, 105,” she said. “You?”

“Six five, 240.” I answered.

She leaned down and licked my ear with her tongue, and whispered, “Take me. Dominate me. Own me.”

I stood up, easily holding her with one arm and carried her to her bedroom. I set her down on her feet and stood next to her bed, then reached out to undo the tight top that covered her breasts. It fell to the floor, her perky young tits and tiny pink nipples standing firm.

I sat on the bed and fondled her tits, and asked, “How many boys have played with these gorgeous tits?”

“About twenty,” she answered.

I leaned forward and licked a nipple, then ran my unshaven face on them, scratching her lightly and causing her to squirm.

“How many have done that?”

“None, just you. Oh God that feels so good.”

I stood. “Undress me,” I ordered.

Taylor complied, pulling my shirt off over my head and running her hand through the light hair on my chest. I put my hand on her shoulder and gently pushed down, signaling to her that I wanted her to drop to her knees. She complied with this as well, and found herself face to face with my crotch.

I had no belt on, so it was easy enough for her to unsnap my shorts and lower the zipper, and then pull my shorts down and off, leaving her face to face with a large bulge in my underwear, and she ran her fingers over the form of my cock through my briefs. I heard her gasp as my cock grew to its full length and the head of my cock began peeking out of the top of the waistband.

“Do it,” I said.

Taylor pulled the waistband over my cock and lowered my underwear down and off, never taking her eyes off of the area between my legs in the process. She reached with her left hand and grabbed my cock around mid-shaft, unable to get her whole tiny hand around it.

“Holy shit,” she said as she slowly pumped it.

“How many dicks have you had in your hand?” I asked.

“About ten,” she replied.

“Have you sucked any of them?”

“Two.”

“Did any of these guys come?”

“Not the two that I sucked. I made four guys come with my hand.”

“Tell me about that.”

“With two of the guys, the situation was about the same. Both times, I was in a car with the guy, making out. With the first guy, he played with my tits. I pulled out his cock and he shot his load in about five seconds. Same with the second guy, about a week later, except I let him finger me. He came in about ten seconds after I touched him.

Two other guys were hookups at parties in college. Same type of thing. They fingered me and wanted to fuck me. I said no, but I’d give them a hand job. They came quick too, one in my hand and one all over himself.”

“Was it a lot of cum, any of them?” I asked.

“Not really, one guy was clearly more than the other three, but I wouldn’t say it was like a crazy amount. About what I expected.”

“How big was the biggest dick you’ve had in your hand?”