Taking an old [F]riends virginity one su[M]mer

This takes place exactly a decade ago this month. 18 year old me gets a text from Heather. Heather is a childhood best friend that I grew up with and lived around the corner from. We have a lot of history. None of it sexual until now. We just graduated high school and both turned 18 recently. Our conversation goes something along the lines of “hey. I need to ask a favor. A serious favor.” I’m typing from memory, none of this is direct quotes, just a summary.

Me – everything ok?
Heather – yeah, it’s something personal though and I don’t know how to say it.
Me – I can’t help if I don’t know what the deal is.
Heather – ok, fine. I want you to take my virginity.
Me – are you fucking with me?
Heather – I’m still at work, I’ll come by after I get off.

Now at my house…

Heather – you’re one of my oldest friends. You’ve always had my back and been good to me. I trust you and I know who you are. All of my friends have been talking about sex lately and I’m the only one that hasn’t had sex. I think about it all the time and I want to do it. I want it to be you. So?

Me – if you’re serious, then we need to do this the right way. So that being said, today is Wednesday, think about it and if you still want it to happen, then it’ll happen Saturday night. You’ll come over and we can go from there. Deal?

Heather – deal.

Heather was cute. Always has been and still is today. She’s only three weeks younger than me. This was my last summer before boot camp and I wasn’t gonna turn down a hot girl before I was on lock down. I obviously wanted to do it, but like I said, she’s one of my oldest friends and I couldn’t just rush into it despite my teenage brain saying yeah fuck it do her right here right now.

She had long dirty blonde hair. About 5’6”. Happy personality. Always in a good mood. Really pretty smile. Nice perky B cup, a fit ass and nice legs from volleyball and softball. She’s in great shape from playing sports. Actually, she resembles Elizabeth Banks. A girl next door vibe.

Anyway, Saturday comes around and I get a text on my super rad razr flip phone. “I get off at 8. When do you want me to come over?” I tell her whenever is cool with me. She shows up around 10. My bedroom as a teen wasn’t connected to my house. You could either go in my room or into the house. Growing up, I had the party pad. She’s sitting in my room looking nervous as fuck. I’m standing in front of her when I say, step one, get naked and I take my clothes off Already semi hard. 18 year old me didn’t have the restraint I have today. She stands up and getting down to her bra and panties. She’s smirking nervously. “Here goes nothing…” they hit the ground. I can’t believe I missed out on this my whole life. Little tiny pink nipples. A pretty bald pussy with a little labia barely exposed. I said “no more secrets now.”

I step up to her and tell her to do whatever she wants. So, hesitantly she looks at my nude body while I look at hers, and reaches down and grabs my cock feeling every inch of it with her soft hands. 18 year old me… rock solid. We look like two blind kids having sign sex. I grabbed her hips and pulled her in so we were pressed against one another. I lean down and start kissing her. Her hands find a place on my hip and neck. Restraint was the key to pulling this off tonight so I had to take it easy.

I suggest we do oral on one another to get the night started. I’ll go first since I’ve done it before. She agrees and lays on my bed. I wasn’t nearly as good at it as I am today, but I knew the clit equated to orgasms. So I get down and begin a little foreplay. I kiss her inner thighs and get devilishly close to the hot spot teasing her. Finally, I start licking her clit. I hear her say “woah. That’s what all the hype is about.” I slide my finger in her pussy for an added sensation, and it worked. She was into it. Her first sexual experience besides masturbation was off to a good start.

I keep at it for a few minutes when she starts to loosen up and looks down at me. She had a sexy body. I had seen it in bikinis, but full frontal makes a world of difference. Still licking and I feel her fingers through my hair. She tells me to stop. “You ok?” She’s silent for a few seconds then says “can I try you?” But of course. I lay against the pillows when she asks “what exactly do I do? Like do I lick it in my mouth, orrrrr what?” I had never had to explain a blowjob before. I didn’t know how. I said “most important thing is no teeth! Ever. The tongue and lips do the work. Deeper isn’t always better. Watch my reactions and go off of that you’ll know if I like it and you’ll know when I don’t. Just start with the tip and keep a loose grip with your hand, but firm enough so it doesn’t shift around.”

She took that advice to heart because right out the gate… wasn’t bad. She would work the tip with her lips and press her tongue on the bottom of my head. I told her my sweet spot was right where the tip meets the shaft on the bottom side. Her tongue would glance it just enough to get a reaction out of me. Compliments helped. She tried going deep, but only made it about half way down before gagging. I was only about and inch and a half shorter than I am now. Probably 6 inches on the dot.

Then I suggest we 69. Kinda my personal favorite as a teen. So, the team player she is, mounts up and straddles my face. Great view. I like watching a woman’s asshole pucker whenever I hit that sweet spot. All of her spots are sweet. It’s all new. She starts sucking me off again and I return the favor. She’s pretty wet. I’m anticipating the sex now. She lets out a few uncontrollable moans whenever I flick her clit. I wasn’t quite the oral sex wizard I am today so no orgasms just yet. We 69 for a minutes when I ask her if she’s ready. Heather takes my dick out of her mouth and says “this is crazy. I can’t believe we’re about to have sex.”

She’s nervous. But I knew what I was doing. I’m not about to fuck her like one of the hoot rats I learned from. I’m here for her. “How should we do it? What position is better?” I suit up with condom because I’m considerate and respond “tonight’s your night so the position is up to you. You can be on top and be in control or I can be on top and you guide how deep I go.”

Heather decides to be on top and she’s sitting on my stomach with my hands on her legs. She’s trying to rationalize what’s about to happen. “You can stop if you want. No rush Heather. Really.” She takes a deep breath and gets in position. She was horny and confessed to watching a lot of porn in preparation for this moment. No backing out. There was a little wet spot where she was sitting. To my surprise, before she lowers down on my cock, she says “I feel like it’s gonna feel weird with a condom on. Can I take it off?” I was shocked. She peels it off of me and I feel the cool air hitting my eager cock. Heather turns the sexy up to 11 and sits on it. It’s pressed between her pussy lips lubing me up. I was so ready to put it in her.

I prepared earlier in the day. I had a towel and some baby wipes ready for the hymen. Got some lube and condoms we didn’t even use. I put a little lube on my fingers and rub it over the opening. She’s smiling nervously again. It’s kinda cute and turns me on how much she was willing to go through with it but was still sorta shy. When knew pretty much everything there was to know about each other, this was basically all that was left. She’s lubed up, I’m hard as a rock, and we’re both ready. She start to lower down on me. I’m watching her virgin pussy swallow my cock when she gets to the bottom. She seemed like she was in pain so I told her take her time. We had all night. She starts to move her hips a little trying to keep the momentum. I can see a little blood so I stopped her and we cleaned up.

Heather – well, we did it.
Me – that was it? You don’t want to keep going?
Heather – should we?
Me – (gesturing to my erection) I think so.
Heather – how much comes out?
Me – depends on a lot of factors.
Heather – well I wanna see now. I’m curious.
Me – did you get close earlier?
Heather – I honestly have no idea.

I lay back down and she straddles my waist. I rub her pussy and get her in the right mindset. Now I’m all giddy. Heather leans forward and grabs my dick slowly sitting on it. She has a drastically different look on her face this time. “That feels so good. I’m glad we’re doing this together.” I couldn’t agree more. She felt so good. The pinnacle of my sex life at that point in time. And by default I was hers. I guide her body into the right motion. Up and down pivoting her hips back and forth. She gets it pretty quick, and just like that, we’re fucking. Her little pussy is sliding with ease. She’s really into it. I start sucking her nipples trying to get an orgasm out of her.

I’m not gonna lie, I jerked off like 4 times that day in anticipation for this night. I was good to go. Now we can experiment. Heather wants a new position so I suggest old faithful… doggy style. She gets on her knees and looks stiff. I put on her elbows and arch her back. Sex is just as much a visual as it is physical. The adjustment helped. I start to fuck her from behind and she is very vocal for it. “Ohh god damnit! That feels so fucking good!” as her toes curl and she gets a handful of my sheets. Her perky tits shake with each impact. She’s really into it. “Right there! Whatever you’re hitting keep hitting it!” I knew I could make her cum now. I tell her to rub her clit and almost immediately she says “somethings happening. It feels tingly but really intense. I think it’s an orgasm!”

I start fucking her as hard as I can. She’s still rubbing herself and a few more seconds of hardcore penetration go by when she experiences her first vaginal orgasm. “I think I’m cumming! Yep! I’m cumming!” she yelled into a pillow. Her little virgin butthole was winking at me. I could feel her tight pussy throbbing around my cock like shockwaves. I was proud of myself. It didn’t last very long because I assume since it was her first time, it was a lot to take in. She rolls on her side and feels her own heart beat, eyes all wide grinning from ear to ear. “I’ve been missing out on so much. I feel cheated. It lives up to all the hype.” blushing looking all cute and proud of herself.

We had been at it for about 30 minutes now. Most of it was instructional and practical application, but still an important part of the process. I told her to be vocal with me. If it feels good, tell me. If it’s just meh, I wanna know. If I hurt you, don’t endure it for my sake. Now she’s laying on her back and we start missionary. Nothing crazy, just standard sex. “If you want it to feel good you have to participate.” I put her hand down on her clit and she starts to play with herself. Now we’re getting somewhere. I wanted to spice it up, so I put one of her legs up pinning it back with my arm. A new sensation which is very obvious from her ecstatic facial expression. A little harder and we find the perfect tempo. She grips my forearms pretty tightly. Her wet fingers dig into my skin. In that moment I pick her other leg up and pin it behind my arms. She’s spread wide helplessly taking a pretty good fucking. Heather breaths harder and harder with each thrust. “Talk to me.” I tell her. Her struggling to talk, “It’s good. It’s really good. My favorite so far. I think I’m gonna cum again.”

Every time I slam into her, we make that flop sound. Perfect strokes. I felt like we heard it a thousand times when out of nowhere she arches her back presenting her cute little tits and she covers her mouth. She’s cumming. It snuck up on me, but god damn did she feel this one. It lasted significantly longer than the first. Probably 15 or so seconds of pure bliss for her. When she’s done I ask if she wants to do another position when she suggests, “well when are you gonna finish? Are you even close?” I said yeah, I could wrap it up if you’re ready. She says “well, it’s all great so far, but I wanna see what it looks like when you finish. How much comes out? Does it taste funny?”

I didn’t bust the shot glass worth of cum I can do today, but for my age it wasn’t bad. “Probably a little more than two tablespoons. And as far as I know mine isn’t bad. I haven’t heard any negative feedback.”

Heather – are you gonna do it on me?
Me – generally that’s where it goes unless you swallow or have a condom on.
Heather – I’m nervous about swallowing. I feel like it’s gonna choke me.
Me – you can stroke it on your tongue or on your chest.
Heather – I’m kinda curious about the taste though. Maybe I can do both? Like a little in my mouth and the rest on me? Is that feasible?
Me – there’s definitely enough to do both.
Heather – ok so now what? Do we keep having sex or is it ready to go?
Me – want more blowjob practice?
Heather – don’t call it practice!

So I’m sitting on the edge of my bed and she’s sitting on my drum throne. She’s at the perfect height and begins to suck my dick and she says “I thought it would taste funny since it was just inside of me, but it’s not bad. Not even really a taste.” I told her to use her tongue like she’s feeling for something. That was what changed the sensation for me. Her tongue is making short work of me now. Lots of pressure on the bottom of my cock. Long smooth stokes. Deeper than the first time, easily taking a little over half of me. Her red lips sliding up and down in complete control. “How am I doing?” She was killing it. Paused a lot to catch her breath, but still doing excellent. I put my hand on the back of her head guiding her. Her perky little tits look great as a background image to the mouthful of dick she has.

I’m about to finish when I tell her to get ready for it. “Don’t stop when I comes out. If it’s too much then switch to your hand, but keep going until it’s over.” She responds with my cock in her mouth “Mhmm.” A few seconds tick by when the throbbing starts. Her eyes get wide when the first gulp blasts into the back of her throat. What a professional. She didn’t even pause. A few pumps of cum shoot out when she removes her mouth and gets on little shot on her chin. She did exactly as I said and used her hands. Hands plural. One on top the other. It’s splashing on her chest and neck. She’s laughing as I’m cumming on her. I couldn’t believe how cool she was about all of it. After I finish, she just looks at my dick with a little drop running down the shaft. “It wasn’t bad. It was kinda sweet and kinda salty at the same time. I even swallowed a little bit!”

She puts her hand up for a high five. Couldn’t leave her hanging so I reciprocate. She’s looking down at her chest and says “how come all this is so liquidy when the ones in my mouth were really thick?” I shrug, “just how it is.” I toss her the towel and baby wipes and after she cleans up she’s asks “so do I have to do my first walk of shame or can I just sleep over?” Nothing changed. “Dude you’re cool to crash. You sleep here all the time, this isn’t any different.” I throw her a shirt and wouldn’t you know it, she asks if we can sleep naked. “I’m still trying new things. This would be new.”

Heather sleeps over and for about a month we had sex almost every night. We tried pretty much everything except anal play really kinky fetishes. We did shower sex. Pool sex. Car sex. My last summer before boot camp was a pretty busy one

Source: reddit.com/r/gonewildstories/comments/8rhk13/taking_an_old_friends_virginity_one_summer