(NOTE: Quite a bit of build-up in this story. Scroll down to the line break if you want to skip it.)
My girlfriend and I were both out of college, but still in our early 20’s. I’d just returned home from a week-long business trip, which was the first time that my girlfriend of just over 3 months and I had really spent any real time apart since we’d started dating. The night before I’d left for that trip had been a great one — [she gave me my first blowjob](https://www.reddit.com/r/gonewildstories/comments/1psv3j/remembering_my_first_blowjob_mf/), which was also the first one she’d ever given.
She hadn’t wanted to do anything else that night other than cuddle. The next day (a Sunday), I left for my trip but I made sure that flowers were delivered to her so that she’d know that I was thinking about her while I was away.
I returned home late on a Friday night, so it wasn’t until Saturday (exactly a week later) that we were able to see each other. That Saturday night was one of those perfect early-in-a-relationship nights of sexual tension and excitement, when you know sexy things are going to happen but a big part of the fun is the anticipation and lead-up to it. My girlfriend was house-sitting for a friend of hers that weekend, so we had a house all to ourselves for some alone time on Saturday night and all day Sunday.
I had picked up some dinner on my way over, along with two bottles of wine for us to drink, and a small bottle of whiskey for myself. It was summer and very warm, so I was treated to a wonderful sight when she answered the door in a low-cut red tank top and a pair of tight shorts. She was 5’7″ and at that time she had long, curly brown hair that went halfway down her back. Her gorgeous C-cup breasts were underneath the tank top, and she’d clearly chosen her outfit to show off her cleavage and have me drooling over her all night.
I told her she looked great and how much I missed her, and we did some brief making out in the hallway before we stopped long enough to eat dinner and to start into the wine. After dinner, it was still pretty early and we needed time to digest before fooling around, so she gave me a tour of the house that she was watching for the weekend — complete with stolen kisses and little bits of fooling around in different rooms. When we got down to the basement, I got my idea for our next activity.
“You didn’t tell me that there was a pool table in this house.”
“I don’t really play, so I didn’t think to mention it. But we can give it a try if you like.”
So we got the wine and the whiskey and played some pool. She wasn’t very good at it, but it didn’t matter because the goal was just to have fun. It gave her an excuse to lean over the table and give me a bit of a view down her shirt, and it gave me an excuse to give her “advice” on how to hold the pool cue, which we both knew was just an excuse to get behind her and press up against her tight ass. We were teasing each other shamelessly, and we knew it.
Between the wine and the booze, we were both feeling no pain, and I was looking for a way to turn the sexual tension up even a bit more. We were between games, and standing near the table hugging and kissing, and taking sips of our drinks.
“You know, we should put some sort of wager on the next game, just to make it a bit more interesting.”
She laughed heartily and playfully pushed me away. “Of course that’s what you want, since you’re much better than I am at this. What kind of wager did you have in mind?”
I pulled her in closer and with a kiss or two on her neck, moved my mouth around to her ear and whispered in to it “I’ve been thinking all week about [how good you made me feel](https://www.reddit.com/r/gonewildstories/comments/1psv3j/remembering_my_first_blowjob_mf/) before my trip, but I didn’t get to return the favor. So how about we play where the loser goes down on the winner?”
Again with a laugh — I’m predictable, but that’s kind of the point. She’s going a long with it. “Oh, what a surprise! I would have never guessed you’d come up with a wager like that. But I’m glad you liked your pre-trip send off!”
“It was the best feeling I’ve ever had.”
“Your idea isn’t fair. You’re guaranteed to win unless I get lucky and you hit in the 8 ball.”
“How about I give you two shots for every one shot that I get?”
She thought about it, and had a bit more wine. “Three shots.”
Now, of course I wanted another blowjob, but what I had really been dreaming about for the past week was getting my new girlfriend fully naked and tasting her pussy for the first time. I’d always had a thing for cunnilingus, but my two previous girlfriends almost never let me go down on them. I was my new girlfriend’s first boyfriend, and the previous week when she’d given me a blowjob she was wearing just her panties. She’d yet to be fully naked in front of me.
So I was planning to lose on purpose anyway. But her “three shots for one” rule would just make it easier for me to lose without having to “throw” the game and make it too obvious. So I agreed.
Of course, with all the wine she was still playing pretty badly, so even while not trying very hard, I still was ahead in the game. Halfway through, she brought me another drink and gave me a big kiss, saying “we didn’t make any rules about me not distracting you”. So she gave me a sexy look while removing her tank top, and continued playing the game in just her white bra (bra & boobs looked sort of [like this](http://i.imgur.com/owYE4LB.jpg)) and shorts.
There was a lot of mutual laughing now, as when it was my turn to shoot, she would make a point of rubbing my butt or nibbling on my ear, or leaning over the table in front of the pocket that I was going for.
Eventually, she won. No complaints from me!
*****
Back upstairs and in the bedroom, we were making out heavily. My girlfriend’s bra was now off, leaving her in just her shorts and panties. I was down to my boxers, and hard as a rock from her reaching in to touch me while we were making out.
She was laying on her back, and I was on top of her, teasing her nipples and breasts with my tongue and lips while she gave little moans of pleasure. “Use your teeth a little bit,” she said, and I started to let her little eraser buds scrape against my teeth. After about 30 seconds of this she pushed me away and said “take my shorts off”.
Kissing my way down her stomach and belly button, I crouched between her legs and undid the button of her shorts and the zipper while looking up at her. She had her head up on a pillow and was looking into my eyes as well. We both had huge smiles on our faces. As I made my move to continue undressing her she said nervously, “only my shorts”. I obeyed, and slid her shorts off of her, revealing a cute (but plain) pair of panties, [kind of like these](http://i.imgur.com/uX5V7pg.jpg).
Knowing she was nervous, after I tossed her shorts aside I went back up and slowed down, kissing her more on the lips and running my hands over her back and her breasts and her ass.
“I’m sorry for being nervous. I want to do more and I want you to go down on me, but you know I’ve never let a guy see me naked before.”
“I know. I don’t want you to be nervous. You’re gorgeous, and I love you, and I just want to make you feel good.”
“So I uh, got my legs waxed while you were away. But… I didn’t, I mean I’ve never, you know, asked them to do everything…”.
“Don’t worry, I think you’re beautiful no matter how you look. Relax and let me make you feel good.”
I kissed my way back down her chest and body, tracing my fingers in front of my lips, teasing her pussy over her underwear with my fingers and eventually with some kisses, going nice and slow and letting her relax and get comfortable. My fingers and lips could feel the wetness of her underwear. She may have been a bit nervous, but she was also ready and excited. I put my hands on her panties and slowly started to pull them down, so that she’d have time to stop me again if she was nervous. But instead, she lifted up her butt to help me get them off.
She was right about having not shaved, but I was fine with that. (It took me some searching, but I finally found a picture that looks close to [how her pussy looked](http://i.imgur.com/gKNmYzr.jpg) that night.) I wanted to taste her and I wanted to give her pleasure and make her cum.
There we were — she was on her back with her head on a pillow watching me in the dark room. This was the first time a man had seen and touched her pussy. I was crouched between her legs having gotten her underwear off, hard as a rock myself with desire and wanting to blow her mind and reassure her.
I looked up into her eyes, while running my fingers through her pubic hair and lightly caressing her labia. She was wet with desire and anticipation. I wanted to re-assure her and make sure she knew how I felt. “You look beautiful. You’re so gorgeous. I love how sexy you look.”
“You don’t mind that I’m not shaved?”
“No, I think you’re beautiful,” I say, breaking eye contact and slowly bringing my mouth down for my first taste of her, and for her first experience of receiving oral sex. I planted my first kiss on her slightly parted and wet pussy lips — a gentle kiss just to give her a taste of what it feels like. The sigh of pleasure that I heard come from her throat let me know that I was doing ok. I kissed her again, and then I used my fingers to part away some of her hair, placed my tongue on the bottom of her pussy and slowly licked my way up to the top, ending by turning the lick into a kiss. She tasted fantastic, and as I finished my lick/kiss I looked up at her and made a “mmmmm” noise that you make when you taste something great.
She looked back at me with a mixture of lust and still some nervousness.
“It doesn’t taste bad?”
As a response, I moved my head back down to her pussy and gave her several more kisses, using my tongue to tease her opening and moaning in the back of my throat. I looked up again — “You taste so good. Just enjoy this.”
I dove back in, and for about 60 seconds I used my tongue to get acquainted with every little bit of her pussy, wanting nothing more than to make sure that her first experience of being eaten out was a good one for her, and wanting her to know that her body was incredible. I french-kissed her labia, slowly working them open with my tongue and getting her juices into my mouth and on to my face. She was moaning with pleasure and running her fingers through my hair.
“Does it feel good?”
“Ohhh, yes! Keep going!”
I kept going, this time with longer strokes of my tongue, getting it as far inside of her as I could, and then slowly bringing my tongue out and moving it up to flick across her clit. The first time I made contact there, she moaned more loudly with pleasure and her legs locked around my head, holding me in place and her hands pushing my head down harder into her crotch. I kept going, reaching around with one hand to play with her nipples while continuing to eat her out. This set off her orgasm and when she finally eased up, she pulled me up to lie next to her. We kissed for a bit — she didn’t mind kissing me even though my face was covered with the aftermath of her orgasm — and we both just basked in the afterglow with smiles on our faces.
By the end of the next day, we’d gone down on each other in the shower, swallowed each other’s cum, and taken our relationship to the next step of physical intimacy.
That was about a decade ago. We’re still a couple (married now), and given the choice of any sexual activity, I’ll still choose going down on my wife and making her cum as my #1 pick.
Source: reddit.com/r/gonewildstories/comments/4c8ofv/giving_my_girlfriend_her_first_oral_sex_and_orgasm
Very well written story! Thank you!
Wow! Made my heart pound. :)
Really enjoyed both this and the old story you linked to!