Trusting Me to Take Her Virginity [MF]

“Paul, I want you to be the one to take my virginity. This has gone on too long, I just want to have sex one time before we leave college.”

How do you respond to something like that?

“Yes please”? Sounds a little too lecherous.

“Okay, alright”? Not serious enough, she’s trusting me with something really important to her here, I can’t just wave it off.

I just took a sip of my coffee and looked over at Maddy. Of course I wanted to be the one to take her virginity. She was one of my best friends, and I’d had to hear far more than I cared to hear about her boy troubles over the past few years. I wouldn’t mind if that was behind me.

Maddy was one of the first people I met in college and she’d become one of my best friends. When I first met her, she was quite shy, someone clearly trying to discover herself in college. Like me, she hadn’t had much success with the other sex in high school, and she came to college with this idea that she was going to find “Mr. Perfect,” and he was going to sweep her off her feet and she’d be happy ever after.

The problem, of course, is that Maddy had awful taste in men, especially as she matured in college. She lost most of her high school awkwardness, and she became a confident, flirty woman. She taught yoga at a local studio; I’d been to her classes, she was pretty good up there, upbeat, flexible, always with a smile. She was smart, pre-med, she literally wanted to be a brain surgeon, and I’d have bet a lot of money at the time that she’d become one.

And she had grown strikingly pretty as well. Gone was the awkward, skinny girl from high school whose pictures she’d shown me, embarrassed, on Facebook. She was a woman, with piercing blue eyes that drew you in and made her seem mysterious, blonde hair that she wore either straight or curly, and a smile that made you want to smile right back, her dimples pulling you in.

But all that newfound beauty didn’t find her “Mr. Perfect,” nor even “Mr. Acceptable.” She’d spent the past three years pursuing the series of men that mothers warn their teenage daughters about. She could fill out a bingo card of bad men: a few frat stars, a hipster with a beard, a guy in a band, a couple of older guys, even a TA in one of her classes. Most of them did her wrong, or she made one of the classic female mistakes and drove them away.

But she didn’t have sex with any of these guys. Maddy wasn’t a slut, and she wasn’t going to have sex until she was in a committed relationship, and she didn’t get far enough with any of these guys to get to that point. Either she would screw something up, or more often, one of them would treat her like shit and she’d end up crying again. I’d tried to set her up with a couple of my friends, and so had her friends, but she’d blown all of our suggestions off as too boring, not cute enough, or something else.

I swallowed my sip of coffee and looked over the table at Maddy, “Why me?”

Her face twisted a little, dropping as she spoke, “I always thought it would be with this guy who I loved, and it would be romantic, and everything. But that looks like it’s not going to happen while I’m here, and I don’t want to be a virgin anymore. I just want to have sex.”

“No, no, I get all that. Sex is very nice,” I said wryly. “But why me, specifically?” I had to ask. This was clearly a really big step for her, one that she had thought about a lot, and she’d come to the conclusion that I was the man for the job, so to speak.

She shrugged, “I trust you. You’re attractive enough…”

I sarcastically muttered, “Thanks for that,” my eyebrows raised.

“Don’t be an asshole, Paul, you know what I mean.”

I smiled, “Sorry. Keep going.”

She continued, “Like I was saying, you’re cute and I trust you to treat me with respect and everything.”

I nodded, “Of course Maddy. Thank you, that’s sweet.”

I sat back and took another sip of coffee, thinking about why Maddy and I had never dated. We probably should have, I thought to myself, just things never worked out. We’d both spent freshman year trying to find ourselves, two high school nerds who had to learn (mostly the hard way) what college freedom was like. I dated someone sophomore year, the sex was nice but everything else was not. And junior year she was abroad for half the year.

But we’d always been close, and now that we were seniors, she was ready to entrust me with this privilege. Like I said, looking back, I should have dated her instead of whatever I was wasting my time on, but those mistakes had already been made.

I took another sip of coffee. “What are you doing on Friday?” I asked her.

Maddy thought for a second, “Friday’s no good, how’s Saturday?”

“Yeah, sure, that works for me.”

We stayed and chatted for a while, but the atmosphere between us had completely changed, albeit in a subtle way. Even someone who knew us well might not have been able to see it, but suddenly there was an almost-tangible sexual tension between us. Her eyes lingering on my shoulders and arms as I reached for something. My eyes locked on her body as she walked over to throw something away. That small, almost imperceptible, flush in her cheeks as I made a joke. The warmth of her body on mine as we hugged goodbye, the hug lasting a few seconds longer than usual.

She turned around and smiled at me as she walked off to class. I’d seen it a thousand times, but that combination of warmth and mystery that her smile exuded seemed to draw me in more than usual. As I stood there, I realized how much I wanted what she was offering me, how for the past couple of years I’d wished this day would come, yet never seriously thought it would.

When I say that we should have dated, that’s not because there were chances that either of us turned down. In fact, she’d never shown any interest, nor did I get any hints from our mutual friends that she was interested. So her offer that day came as a bit of a surprise, I just didn’t know she saw me like that: as a man to be attracted to and have sex with.

It was only Tuesday, and now I had to wait until Saturday. I thought about her body all week, I just couldn’t stop thinking about her.

Saturday finally came, and that morning I sent her a text, “Hey, you wanna grab dinner tonight, or am I just coming over later?”

An hour passed, no response. Was the deal off? It couldn’t be, I’d thought about it too much all week, that one conversation had made me fantasize too much about her to then not go through with it.

I was starting to really freak out when my phone finally buzzed, “Hey! Sorry I was at yoga. Dinner sounds great, I’m free at like 7:30. You?”

“7:30 is great, see you then”

We made plans to meet up at the taqueria with $5 margaritas, I think we both figured some alcohol would take the edge off what could be but hopefully wouldn’t be a very awkward night. I decided to dress causally, not make things too serious, so I wore a white v-neck that I knew I filled out, dark skinny jeans, and Stan Smiths.

I got to the place a little before 7:30 and got a table, sipping a margarita. I ordered one for her, and she came in and sat down, thanking me for the drink. It was a slightly chilly evening in early fall, and she wore a bright red cardigan over a white t-shirt tucked into ripped jeans, with black Adidas sneakers. She’d curled her hair and pushed it back behind a headband, it curled just as it passed her shoulders, the color catching the light in the restaurant.

We chatted over multiple margaritas, really catching up on how our semesters had been going and somewhat reminiscing over our time there. A couple of times during the conversation, I caught her taking a peek at my arms and shoulders, poorly contained by my shirt. And I couldn’t take my eyes off of her. She’d done her makeup as well, and she looked incredible. How had I not appreciated her beauty before now?

I was starting to feel the margaritas a little, and I knew it was time to move things along. I certainly was ready. I finished my margarita and smiled at her, “You ready to take this back to your place?”

She smiled nervously, nodding.

I paid and we walked back to her apartment. She’d picked Saturday because her roommate was out and Maddy wanted the apartment to herself. She fiddled with the keys to unlock the door, her hands shaking slightly. I reached out and held her hands, clutching them in mine.

I looked down at her, my eyes meeting hers. “You’re nervous,” I offered.

She nodded. My right hand still holding hers, my left went around her waist, pulling her gently towards me. She titled her face up to me, her eyes wide. I leaned down and kissed her, her lips were so soft, a little sticky from her lipstick.

I brought my right hand up to caress the side of her face, resting on her jawline. “Don’t be,” I said softly. “Okay?”

She nodded, and I brought her into me, her head resting on my chest. “Come on, let’s get inside, unless you wanna do it out here,” I went with humor, hoping it would lighten the mood a bit. She opened the door and I followed her inside.

The apartment was empty and chilly, I could see the goosebumps on Maddy’s skin as she took off her cardigan and tossed it on the couch. I grabbed a blanket and headed back to her bedroom, where I lay down on the bed and waited for her to join me.

She came in a couple of minutes later and just stood in the doorway, waiting. I motioned with my hand for her to come over to me, patting the area next to me. She laid down, and I moved to spoon her, my left hand under her neck, my right snaking around to pull her close to me.

“You’re still scared of me,” I whispered in her ear.

“Sorry, it’s just intimidating.”

“Just close your eyes and relax,” I reassured her. “If you’re uncomfortable with anything or if you need me to go slower, just say so, okay?”

“Okay,” she whispered, almost too quietly to hear.

I brought my right hand up and moved her hair out of the way, and I softly kissed her neck, taking my time to appreciate the smoothness of her skin, it warming with each breath onto it, then cooling as I kissed it.

“Is this a new perfume?” I murmured into her ear.

The kisses made her breathe a little heavier, “Yeah, I got it over the summer.”

I inhaled, taking in the new scent, “Mmm, I like it.”

As I kissed her again, my right hand explored her body – her toned shoulders, her incredibly tight stomach, those perfect legs, thin but muscular, before finally coming to rest on her small but shapely tits, my hand easily taking one within my grasp and squeezing lightly.

She exhaled with a soft moan. She didn’t have to say anything, I knew how she was feeling from everything she did, how she lifted her head to give me easier access to her neck, her breath quickening from my touches, her ass starting to move against my pants behind her, her nipple hardening as I twisted it between my fingers.

My left hand reached from under her to tilt her face up to mine and I kissed her, feeling those soft lips again against mine, her tongue darting into my mouth to dance against mine. She spun around so we were now facing each other, one hand clutching the side of my face, feeling the stubble, the other running all over my body – my shoulders, my chest, my abs.

I pulled her on top of me, her small, tight body resting on mine. Her kisses came with more passion now, and as she pushed her crotch more forcefully against mine, I reached down and squeezed her ass, small but shapely just like her tits, pressing it down even harder against me.

She brought both hands up to my face and kept kissing me. We lay there for a long time just kissing. I was in no rush, I needed her to be more turned on than she ever had been, her thoughts moving from nervous to turned on. I could tell that she was well on her way.

I rolled over so I was on top of her, letting her feel the weight of my body on her and how much smaller she was than me. I kissed her again, then dropped my head down to kiss her neck, she moaned as I moved down.

I pushed myself off of her and stood at the foot of the bed. I pulled my shirt over my head, her eyes widening slightly as she looked at my body. I undid my belt and unbuttoned my pants, letting them slide to the floor as I stepped out of them, my hard cock outlined in my briefs.

I crawled over to her. “I think you’re a little overdressed,” I said with a glint in my eye.

She laughed, “I might be.”

She was definitely getting more comfortable, then. She sat up and reached her arms over her head, I pulled her t-shirt over her head and reached behind her to take off her bra. I leaned my head down to her tits, running my tongue in circles around her nipples, flicking it over them, my eyes looking up straight into hers as I did.

She moaned, pulling my face up to hers. I gently pushed her back down onto her back and unbuttoned her jeans. I slid them down her toned legs, leaving her in just her white lace panties lying there on the bed.

I ran both hands down her body, “God, you are so sexy.”

She looked up at me kneeling over her. “How long have you thought that?” she asked, in a very serious tone.

I was taken aback, “Uhh, a couple of years I guess.”

“Why didn’t you say something?”

I was defensive now. “I don’t know. I’ve wanted to, but there was never a time. And I didn’t want to ruin our friendship,” I said honestly.

“You really think that?” Her eyes were so big looking up at me. I just nodded, looking down at that pretty face and sexy body. In that moment, I wanted her more than I’d ever wanted anyone.

“Come on, let’s get these off,” I said, sliding her panties down, she lifted her hips so they could slide off. There it was, her pussy, visibly wet even without having been touched. I ran two fingers up and down her lips as I bent down and put her nipples in my mouth again.

“Is this okay?” I asked, wanting to make absolutely clear that I wasn’t pushing too fast.

“Yes,” she moaned with a deep exhale, turning such a short word into a long one.

I pulled her legs back to open her pussy up for my mouth. She grabbed her feet with both hands and pulled them back over her head, leaving her pussy facing up to the ceiling. I held both her thighs, helping her keep her legs back. With my tongue just inches from her pussy, I looked up at her.

“Ah, so you’ve done this before,” with a heavy emphasis on this.

“Yeah,” she smiled. “Boys will do anything you ask if they think you’re going to have sex with them…”

I just laughed, at least she was self-aware. And flexible, “I don’t think there are too many people who can do that,” I pointed up to her legs up in the air.

She shrugged, “I like it better this way. It makes me cum harder. You really should do more yoga.”

I let out a deep breath, “You’re really good up there, so with all due respect, I fucking hate yoga.”

She smiled again, “Your loss…”

I leaned down and ran my tongue up and down her pussy twice, before letting my tongue flit over her clit.

“Yes,” she moaned, lifting up her head to look at me, before dropping it back down to the bed in pleasure. I put my mouth over her clit and sucked on it, my tongue lightly dancing across it. She reached her hands forward, grabbing onto my hair and pushing my head down onto her.

“Fuck, you feel so good,” she murmured as her pussy started to grind against my tongue. “Right there.”

All of a sudden, with a sharp “Ah!”, she came, her head back, her hands gripping my hair so hard I thought she might pull some out. I licked up and down her pussy one last time, feeling her twitch as my tongue moved.

“Come here, you’re so fucking good,” she dropped her legs down and pulled my head up to hers. This kiss was different, wetter, her mouth wide open as she stuck her tongue deep into my mouth in appreciation.

I pulled my mouth off of hers and looked down at her, “You ready? It’s okay if you aren’t.”

She just nodded. I got off of her and stood up, sliding my briefs down and letting my cock spring out. She reached for it, her hand closing around it and slowly stroking it as she looked up at me standing over her.

Now it was finally time to get to business. “Lube and condoms?” I asked.

“Top drawer,” she pointed.

As I grabbed them, I looked over at her, waiting for me, “How are you feeling?”

“I want it,” she said, staring right at my cock.

“Not too nervous?”

She shook her head, “A little, but I’m okay.”

I nodded, walking over to her, the lube in one hand, the other spreading lube on my rock-hard cock, all seven inches from base to tip.

“Let’s get you ready,” I told her, putting lube on my fingers and reaching my hand down to slide two fingers inside her.

“Oh my god, you’re tight,” I said, barely able to get my fingers into her pussy, but accomplishing the goal of lubing her up. I was very unsure that she could take my cock, but there was absolutely no chance that I was leaving that room without trying.

“Lie on your side,” I commanded, gently helping her roll into position. I lay behind her, again spooning her.

I kissed her neck and felt her body melt into mine, my arms holding her close. “You trust me?” I asked between kisses.

She nodded, “Please Paul.”

“It’s gonna hurt, okay? I’ll go slow, I promise.”

“I know. That’s why I wanted it to be you.”

Wow. My cock couldn’t get any harder, but hearing that almost sent me over the edge. Holding her with my right hand under her neck, I reached down with my left and positioned my cock at the edge of her pussy. As I started to slide it in her, I met resistance – a lot of it.

“Fuck!” she cried out in semi-agony as I entered her slowly, not even inches at a time, maybe centimeters at a time. I pulled her face to mine and kissed her, in the hope that it would relieve even a tiny bit of the agony.

“I know it hurts,” I whispered in her ear. “You’re so sexy and you feel so good.” I wanted to reassure her in any way I could.

The process probably took fifteen laborious minutes as she slowly adjusted to my size and the pain subsided. I slid myself most of the way in and out of her slowly, her moans now back to the pleasure I’d heard earlier, one of my hands holding her body close, the other squeezing her tits.

She was ready. With one deep push, I thrust my cock all the way into her. “Oh god, fuck that’s deep,” she let out. I did it again, letting her feel all of me with long, deep strokes. I’d never felt a pussy as tight as hers, it gripped my cock like a vice, trying to milk me with every thrust.

Still sliding in and out of her, I asked her how it felt. “Fucking good, don’t stop,” was all I got back. I sped up, the slaps of my body against hers, her moans, and my grunts filling the room. Soon, I was utilizing the full length of my cock and my lower body muscles to take her hard, my cock pounding into her, my right arm around her neck choking her and holding her in place for me.

The tightness of her pussy was going to make me cum, and I wasn’t ready yet, I wanted her first experience to be an even more memorable one than it hopefully already was. I pulled out of her and let her roll onto her back. I kneeled above her, my cock hanging down, I looked down and just took in the mental image of that toned body, her nipples standing at attention, her stomach covered in small beads of sweat, her eyes closed as she caught her breath.

She opened her eyes and looked up at me. She didn’t have to say anything, she just tapped her lips with one finger. I leaned down and kissed her, our kisses more passionate now, more urgent. As I did, I positioned my cock at the entrance to her pussy, her legs spread wide, ready for me.

Instead of lying on top of her, I leaned back on my heels as my cock slid into her, slowly stretching her out. She gasped and moaned as I filled her up, “Fuck me, that feels so good.” I sped up and leaned down, lying on top of her, I wanted her to feel what a good pounding felt like.

One of my hands behind her head held her in place, the other on her throat, choking her lightly as I slammed my cock into her with all my strength, as hard, deep, and fast as I could go. And she loved it. She gasped out, even through my choking, “Oh god, oh god, yes, yes, yes, fuck me!!!”

I was getting close and I surrendered to it. I let her pussy have its way with me. With three long, last, deep thrusts, I grunted loudly and shot my cum deep into her pussy, filling the condom, her body twitching with each spurt. My orgasm finished, I collapsed on top of her, out of breath. She too breathed heavily, her nails digging into my upper back, her legs closed tightly around me.

I kissed her, “Wow, you’re amazing. How was it? Was sex everything you’d hoped it would be?”

She laughed, looking down at my cock, “I probably should’ve started with a smaller cock. But it was amazing.” She kissed me, then looked up at me, her hands caressing my face, “Thank you Paul, you were perfect.”

“Of course Maddy. I wanted it to be a special night for you.”

She smiled, no mystery in her smile this time, only happiness. “It was,” she said in a quiet voice. I got off her and started to clean up and put my clothes on.

“Hey Paul.”

I turned to look at her. “You want to spend the night?”

A postscript because I know people will ask. Maddy got what she wanted after all. She wanted to have sex with someone she was in a relationship with, and it just happened to be in the reverse order. Instead of the relationship coming before sex, sex came before the relationship. For the rest of our senior year, we were inseparable – even though we knew we’d be heading to opposite sides of the country afterwards. We made it work for a couple of years, and they were wonderful years, but in the end, it didn’t work. I suppose that’s a story for another time.

Source: reddit.com/r/gonewildstories/comments/7klh4r/trusting_me_to_take_her_virginity_mf