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The original was posted on /r/gonewildstories by /u/xtrafun3987 on 2023-09-20 01:58:41.

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I’m a 26 F now, but long before I got into group sex and truly realized what a slut I was, I still had many dirty thoughts, ideas, and urges flowing through my mind. By the time I reached the end of my senior year of high school, I’d had sex with a few guys, but hadn’t really done much out of the ordinary. I was smitten with a boy at my school, “Henry” (We were both 18 at the time). We had hung out a few times, had made out a bit, but hadn’t done much more than that. He was a virgin, and he knew I wasn’t. In my experience, that dynamic usually works in my favor, giving a clear signal that, you know, I have had and like cock inside me.

In my early years though, I had a tendency to attract sweet, nice boys who weren’t quite as daring or forward. I did, however, start to realize that most people are looking for a permission structure to express and act on their true desires. No one wants to go too far or push a limit for fear of upsetting their partner, risking the relationship, or just being too nervous about what the response will be. Taking less risks might keep your feelings safe, but it’s not gonna do much for your sex life. Games are a great way around this problem, and a strategy I’ve used on occasion very effectively.

I had gone over to his family’s place one night - his parents were out and we were the only ones there, and we were making out on his bed. I took his hand and moved it from the back of my neck to my breast. He stopped and asked “Are you sure?” I responded, “Yeah, that’s why I moved your hand there silly!”

After another few minutes of nothing much happening, I got up and announced we were going to play a game called “Are you nervous?” that I’m sure many of you played as teenagers. It’s pretty simple, you put your hand somewhere on your partner’s body, usually starting at their head or feet, and ask, “Are you nervous?”. They respond, usually with “No”, and then you move your hand slightly closer (directed toward a more… “interesting” body part), and ask again. You keep going until the partner says they are nervous and you stop.

“I’ll go first – you lie down, and then I’ll touch you and we’ll play” I said. Confused, but also a little intrigued, he replied “Ok”, and he lay on his bed, his back leaning against the wall.

I touched his forehead. “Are you nervous?”, I sneered. “No”, he laughed.

I moved my hand to his nose. “No”. Touched his lip. “No”. I then licked my finger and slowly put it back on his lip, and then pushed it into his mouth. He sucked it ever so slightly. I looked back at his eyes and tilted my head to the side, essentially silently asking the question again. I removed my finger.

“No”. Excellent.

I removed my shirt, exposing my 34Cs barely contained in an admittedly very boring skin-colored bra. I moved my hand to his ears, gently stroking them. “Definitely not nervous” Henry said proudly, his eyes fixated on my chest, and the empty void between my boobs, seemingly where the answers to all of life’s questions reside if you’re a horny 18 year old.

I moved my hand down to his chest, and climbed on top of him, but then hovered with my ass just above his crotch. “Are you nervous?” “No”

I sat down on top of him in his sweat pants, and felt that immediate stir of an already moderately stiff cock harden. I grinded on him slightly while making eye contact, clearly conveying with my facial movements that “Yes, I did feel that”. He smiled.

I shifted my ass down slightly, and my hand crawled towards his pants, inch by inch, until it was directly on top of his cock, over the clothes. I paused. “No”, he said. I started to rub him a bit, first gently and generally over his crotch, and then more targeted, ending with me solidly holding his cock from outside his pants. I questioned him again. “Keep going” he responded.

I let go of his cock, and slipped my fingers under his pants and underwear, and just barely brushed my finger across his raw cock. “Nervous?” He shook his head.

In a move I’m still especially proud of, with my left hand I moved fully to grasp his cock, and simultaneously with my right, I put behind my back to unhook my bra. In a matter of seconds, Henry went from a light over-the-pants hand-job to me jacking him off while he stared at my fully exposed tits. I slipped his pants down to his ankles, spit on my hand, and continued to thoroughly stroke his cock.

“You’d do anything I asked you right now, wouldn’t you?” I asked. “Uh hu” he responded blankly, his eyes fixated on my chest. “But not nervous?” “Nope”

I let go of his cock, and moved myself up on his body, his cock now directly under my increasingly moist clothed pussy. I leaned forward, my tits hanging over his head, and dropped one of my nipples just above his mouth. I muttered a “hmm?” and he just grabbed my tit and pulled it into his mouth. He fondled and sucked me, and then grabbed my other tit and did the same, all while likely unaware of his girating pelvis and a hard cock trying to find any entrance it could into my pants.

Seeing as how he’d taken a lot of initiative on his own just now, I decided to switch things up and laid down next to him - “I think it’s your turn to play”

It took him a few seconds to come out of his boob induced high (what can I say, happens to the best of us) before he got up to look back at me. I jokingly asked him if he was nervous now, and he said “yeah, a little”

“Trust that I’ll be honest and tell you to stop if I want you to, but otherwise, really go for it, be daring.” I told him. “Now touch me!”

Henry kicked off the remainder of his clothes, his cock at attention, and put his arm on my foot, and we jokingly went through the routine as he inched up my legs, finally arriving at my pussy. I gave a resounding “Not nervous” as he started to rub me over my clothes. He quickly (thank god) started to remove my pants and underwear as I nodded in approval. We were now both fully naked, one hand immediately returned to my pussy, while the other began to massage my breast, and his dick poking my body fucking everywhere as he moved around.

He took a finger and put it at the entrance to my hole and pushed in ever so slightly while looking at me for approval. “Not nervous”. He began to finger me, and fuck, I was WET. This type of slow build-up has and continues to be very effective ;-) Now, to be clear, this inexperienced 18 year old was not exactly skilled in this or any other area so far (not that I really knew as much either at the time), but his finger was inside me, so I was more than sufficiently excited and turned on.

After a few minutes, I shifted around a bit to align my mouth a bit closer to his cock, hoping he’d take the hint. He adjusted, and soon enough, his cock was shooting straight out of his body, inches from my mouth. I don’t remember his exact size or anything, but it was larger than anything else I had seen before that point and was a great looking dick.

He slowly inched closer to me, the head of his cock just barely brushing my lips as I stuck out my tongue to try and bridge the gap. “The game isn’t are you nervous, it’s am I nervous!” I snickered. “And I’m not…” He moved his cock closer and I swallowed it.

I pretty aggressively gave him head and joked “What should I be doing with these arms?” He correctly took my hand and placed it on his shaft and balls. I blew him for a few minutes, clearly aware that If I wanted to fuck him, I’d need to make that happen soon. But seriously, who are we kidding - it wasn’t a question - I wanted to fuck him.

I stopped sucking him and turned over, stuck my ass up towards him and waited. His cocked bobbed around on various parts of my bottom before grazing the entrance to my pussy. He lined himself up and I felt a cock lightly place itself on my lips.

“Are you nervous?” he asked.

He didn’t wait for me to reply, and his cock slipped easily into my well lubricated pussy. He began to fuck me gently, then more aggressively. After about a minute (it was his first time!), he started slowing and I knew he was close. We stopped for a few seconds, and then I told him to lay down and moved on top of him. He was about to speak, but I interrupted him.

“I definitely wouldn’t be nervous if you came inside me, and you have nothing to be nervous about” hinting at my birth control.

I straddled his cock and took him inside me as I started to ride him cowgirl (my favorite). Just the thought of cumming in me was too much for him, and after a few seconds of riding him, he began to squeal as what I have to imagine were ropes and ropes of hot, sticky, fresh, virgin cum plastering the walls of my pussy. He smiled in relief and pure joy.

I got up off of him and cum drained out of me. We laid together, and because I hadn’t gotten off, I began to touch myself a bit, not even super consciously, spreading his cum around. He noticed and grinned happily. He started to get hard again (Oh, 18 year olds…)

“Can we keep playing?” he asked. “Haha, sure.” I said.

He stood up beside the bed and faced me as I sat on the edge, and began to stroke his cum soaked cock directly in front of me. I continued to touch myself, and we both enjoyed that for a bit. (An aside – I cannot recommend mutual masturbation enough. It is so intimate, and so hot. Please try it if you and your partner are into it!)

He moved his cock toward my mouth and placed it on my lips and asked again, “Are you nervous?”

I immediately swallowed as much of him …

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