*You’ll really want to make sure you’ve read Part I of this story before continuing:* [*I love a good challenge: Tricking my way into Aaron’s bed [FM]*](https://www.reddit.com/r/gonewildstories/comments/hsq6q3/i_love_a_good_challenge_tricking_my_way_into/)
As I left Aaron’s car and headed into class, a drop of cum still in my mouth, I could not stop thinking about the previous few hours with him and how unique it was compared to so many of my other sexual experiences. Given how headstrong and determined he was to avoid doing anything with me throughout, I knew we had made quite a bit of progress considering he had just masterbated to orgasm in front of me, while staring lustfully into my eyes throughout. You always want what you can’t have, and at this point, my desire to actually fuck Aaron had taken over and was idling in my brain all day, making staying attentive in class nearly impossible.
I sensed that Aaron would eventually come around, but it might require moving more slowly than I’m used to, which could be a fun little game for me. I wanted to meet up again, so I texted him a few hours later: “Well, that was surprisingly fun. If you’ve got cum on other parts of your body that need licking off, I’m sure I can misplace my keys again ;-)”. I saw the typing indicator pop up and disappear on and off for what seemed like 20 minutes, until it just stopped entirely. Silence.
Given his stubbornness to physically do anything with me, I had a feeling that maybe he had a bit of guilt considering he knew I had a “boyfriend” at the time. I realized I had only really talked about the boyfriend to him in front of other friends where I maybe wasn’t quite as honest about the true nature of my relationship. I’ve never really dated anyone seriously, and “boyfriend” is the term I used at the time to describe one of many fuck buddies I saw regularly without directly having to out my sluttiness. I’m certainly more open about it now, but I wasn’t broadcasting it as much at this point in my life. I figured it was worth a more direct explanation. I texted “You should know, I’m not in monogamous relationship with the boyfriend, or even a relationship at all. I sleep with other people – you’re not causing me any issues.”
More silence and flashing text bubbles until the truth finally revealed itself… “I’m a virgin”. A light went off in my head… of course! I honesty don’t know how I missed this, but it all made a lot more sense, and now we’re in a realm where I have a little experience. Knowing what I know about Aaron, and the way things evolved during our first night together, he seemed afraid of large leaps, but fine with small steps. Like the myth of the frog who when placed in hot water will immediately jump out, but if boiled slowly will eventually be cooked to death. Aaron and I fucking just had to happen gradually. I needed to slowly boil his virginity to death.
Me: “No problem. Love that. We’ll take it slow.” Aaron: “See you tonight?” Me: “Pick me up at 8.”
Game on.
I found a deck of “dirty dare” cards someone had gifted me and thought this would be a perfect way to have some fun with him. They were color coded and ordered by intensity so the lighter cards were more simple “Kiss your partner on their cheeks” to the dark black cards “Make a hook with your finger and stick it in your partner’s mouth while you fuck them from behind”. Pretty good range. When appropriate, the card was split into two sections for a male to do with a female, or the opposite to make the dare work in either situation.
Deck of dare cards in toe and dressed in a light yellow sundress, a bra, and no underwear, Aaron picked me up and I got into his car. I figured we’d get things started immediately. As soon as we were a block off campus, he glanced at me and I hiked up my dress, revealing my naked pussy and began to lightly tease myself to his shock and amazement. After barely a minute of this, I could tell he was already hard with an uncomfortable bulge under his jeans. “Feeling a little tight in there?” I asked, gesturing with my free hand at his crotch. “Want me to help you readjust?”. Without really waiting for answer, I slowly moved my hand towards him, reached down his pants and under his boxers, grabbed his hard dick and pulled it upwards towards his stomach as he breathed a sigh of relief laced with ecstasy. I held on for maybe 15 seconds, giving a slight tug and squeeze before letting go, smiling at him, and then removing my hand. He drove a bit faster, anxious to get home, as I continued to (now audibly) touch myself.
I could tell he was extremely` nervous as he parked and we walked into his house. I may have overdone it slightly in the car, I thought. We went into his room, I told him to relax, and then said “I brought us a little game to play” as I took the deck of cards out of my purse. “These have dares — they are separated by intensity level. You tell me when you want to move to the next level, and we can go as slow and far as you want. Just relax and have fun!” His face lit up the second he saw the dare cards. I may be on to something here, I thought.
“Can I start?” he asked excitedly as we sat on his bed and he reached to the top of the pile.
*Stroke your partner’s hair for 1 minute*. He cautiously moved his hand over to me and began sliding his fingers through my hair, lightly massaging my head. It felt great and calmed us both down a bit.
I pulled the next card. *Nibble on your partner’s ear for 1 minute*. I laughed considering what I had “nibbled” on earlier, but went for it and sensually sucked and licked his ear for sixty seconds, breathing heavily and ending with a kiss on his cheek. He was already hard again.
“We should go to the next level”, said Aaron. Excellent.
We worked through a number of dares pretty quickly involving Aaron taking off his shirt, us kissing on the lips, and me sucking on his finger in a “sexual manor”. “Next Level?” I suggested. Aaron nodded his head.
He pulled the next card. *Removing or adjusting the least amount of clothing possible, take out your penis and leave it out for the remainder of the game.* Aaron looked at me, seemingly for approval, and I nodded back. He unzipped his fly reached into his boxers, and took out his dick. It was pulsing and hard as a rock, and I could tell Aaron was relieved to have it out. I reached forward as if to touch his dick, but then grabbed my next card as I slyly smiled at him. He seemed to be enjoying the tease more than I expected.
We went through a couple more dares that had me take off my dress leaving my wearing only my black bra given my lack of underwear previously, and a card having Aaron french kiss me and my neck. The next card I had said *Spend 7 minutes in heaven with your partner. Move to the next level if you removed any clothing during your time*. From my recollection of being a teenager, you’re supposed to find a dark room or something to do this in, so I suggested his bathroom with the lights off. He seemed excited and with his dick still visible and at attention, reached his hand out and walked me over.
I hopped up on the counter and started a 7 minute timer on my phone, he shut off the lights, and we started to make out. Immediately, I could feel his warm cock pushing against my naked bottom. His hands began to roam around my entire body and I wondered if he was going to take off my bra or not, signaling to me that he was definitely game for more. Minutes went by and as we were furiously making out, I began stroking his cock, and his hands moved all over my bra. Every 30 seconds or so he’d start to move his hands down towards my pussy, slowly brushing by, as the tips of his fingers grazed the short hairs on my landing strip, but then he’d pull away nervously. After the third time, before he could pull away, I took his hand and placed it directly on my now dripping wet pussy, but before we could get any further, the timer went off.
I got up and turned on the light, now disappointed in the realization that none of us had actually removed any clothing. As I walked towards the door to go back to the bedroom, Aaron came up behind me, his hard dick now pressing into my ass, and unclasped my bra. I turned back towards him as it fell to the floor revealing what I know he’d be dying to see all day. He stared intently, just as he did the night before when he saw them for the first time. His hand reached out to touch, but I quickly grinned, turned back around and teased him as I walked back to the bedroom to get the next level of cards out. Aaron excitedly followed.
Aaron pulled a card out and smiled. *Get as naked as the most naked person in the room, and then have them remove an additional item of clothing if they have one*. No such luck in removing more clothing from me! I could tell he was getting uncomfortable though with his dick out through his jeans, so it was no surprise that he quickly tucked his dick back through his fly and then took it all off. We were finally both naked again.
I pulled the next card. *For the next 3 minutes, have your partner put at least one finger inside you and keep it in you as you talk about the most mundane topic you can think of*. Aaron came over to me, stuck his index and middle finger in his mouth to wet them, and then proceeded to slowly touch the outside of my pussy and push inside. I moaned as he finally was inside of me, though also curious what we were going to talk about. He asked me about an annoying group project that had been assigned in the class we shared, complaining about his partners… as he fingered me. Strange, but a little fun? It was honestly hard for me to carry on the conversation – I just wanted him to go harder and faster. After the 3 minutes were up, he removed his fingers and I grabbed them and sucked my juices off of them. I know, not technically part of the dare, but I was so insanely horny by this point, I couldn’t control myself anymore. I was desperate and itching to get fucked by this penis that was inches from me, but we had a couple more levels to go it seemed. He could tell I was getting restless and quickly pulled a new card and handed it to me.
*Take a quick shower with your partner. Have as much fun as you want.*
I jumped up and headed back to the bathroom to turn on his shower, and he quickly followed. As I got in, I distinctly remember realizing that he had surprisingly excellent water pressure for an old, trashed college house. He got in and we immediately began making out under the water, his hands all over my perky, now glistening 34C breasts. He started playing with my nipples and sucking on them, as a finger re-entered my pussy. He then took his other hand and grabbed some body soap and rubbed it on me, soaping me up, paying special attention to my boobs. He continued to finger me until I dropped down to my knees, had him face his back to the water, and finally did what I know he’d been hoping I’d do for the past hour and took him into my mouth. I started to suck him off slowly, then more furiously as he got more into it. I have an upsettingly frustrating gag reflex, but was able to get a good portion of his 5-6 inches in my mouth as I used my hands to massage his balls and stroke his shaft. After a few minutes, I could tell he was getting close and was worried about things ending too soon. I told him he shouldn’t worry about it, that he’d likely last longer when we had sex if he came now, and confirmed his refractory period wasn’t out of line with your average 19 year old (It wasn’t). I picked up the pace, pushed his cock deeper in my mouth, massaged his tip with my tongue, and gripped him tight as I sucked until I knew he was there. He moaned and screamed “I’m coming!” as he shot a massive load in my mouth, which I promptly swallowed. I kissed him, turned off the water, and we got dried off and headed back to the bedroom.
“How about you eat me out until you’re hard again and then we just go for the last card in the deck?”
He immediately smiled. I could tell from his look that while he was a virgin, he had definitely eaten pussy before and loved it. He lifted up my legs and started going to town, teasing me a bit by licking around my labia, before finally licking my clit as I squealed with delight. I’m not a tough nut to crack in this respect generally, but he still exceeded expectations and had me cumming in just a few minutes. After the orgasm subsided, he asked if he could keep going, and I reminded him of my #1 rule to this day – “No one ever says no to an offer of oral”. He started to use his fingers and I helped to guide him closer to my gspot as he licked away at my clit for what must have been 15 minutes straight by the end of it. I had two amazing orgasms, and he was now hard and ready to roll again.
I took the last card from the bottom of the deck. *Play ‘”just the tip” with your partner for as long as you can handle it*
I had never quite done this seriously before, but it’s now one of my favorite things to do with guys. I had Aaron lie on his back on the bed as I moved on top to straddle him. As my pussy hovered on top of of the tip of his penis, he looked at me worried and asked if we should use a condom. I told him I had an IUD, had been STD tested within the past month, and knew he was clean. “Besides, it’s just the tip” I giggled out loud, as if there was a chance in hell this wouldn’t end with me unable to restrain myself any further and pounding down on his cock.
I positioned myself above him and slowly lowered myself onto him, just so the head of his penis brushed against the outside of my pussy. I moved myself back and forth over him, now feeling the juices of my pussy and some pre-cum allowing him to slide across my lips. Slowly lowering myself onto him, and then pulling back, never going in deeper than in inch. Every time I lowered myself, I could tell he wanted nothing more than to push back against me, but I discouraged it by pinning his arms down and warning him not to move. The teasing continued and now it was clear that he wanted me just as much, if not more than I wanted him. I continued to tease him, occasionally taking his dick in my hand and rubbing it on my pussy, sticking it in just so slightly deeper than before, and then pulling out. It was driving him mad.
This continued for what seemed like 20 minutes in my head, but was likely less. I couldn’t restrain myself any more, and started to count down silently in my head from 60 seconds, knowing that once I got down to zero, I was going to finally give in. I continued and as I got to the last 10 seconds, I looked straight into his eyes lustfully, kissed him once, and then in one quick moment, slammed my pussy down onto him as he looked up with a mix of awe, sheer joy, and excitement. He slid in all the way with ease, and I immediately rode him hard and increasingly faster. Event though we’d only been having sex for 10 seconds, the buildup over the past 24 hours had made me want him so bad, I couldn’t help myself but continue to pound him into me over and over, faster and faster until less than a minute into it, he began to grunt and try to squirm a bit to stop the inevitable. I wouldn’t let him – I grabbed his arms, pinned them down again, leaned forward letting my boobs hang low over his chest, kissed him, and relentlessly fucked him until he couldn’t take it anymore and spurts of warm cum filled my pussy.
He stared at me in awe and I could feel his dick pulsing inside me. After a minute, I slid off of him, cum dripping out of me, turned off the lights, pulled the covers over our heads and went to sleep. I whispered in his ear, “Tomorrow morning, I want you to wake me up however you want”
This story has gone on long enough, so I’ll be brief with the rest. I woke up the next morning with a hard cock in my mouth and immediately began to suck him off. He then proceeded to fuck me missionary, ate me out, and then fucked me from behind before cuming inside me again.
We got dressed, and he drove me back to campus and my apartment. He kept looking at me while we were driving, I’m pretty sure wondering if I’d play with myself again. I lifted up my dress and started touching myself again, realizing that without any underwear on, a small puddle of cum and juices had formed on his seat… oops. When we got back and before I was about to leave, I grabbed his crotch, and was surprised to find a hard cock yet again. Knowing that this story of Aaron’s first time would be with him forever, generally being a people pleaser, and not really seeing any other activity in the parking lot, I took out his dick and sucked him off one last time to completion. I left his car, blowing a kiss, having just swallowed warm cum in my mouth, and still feeling cum leaking from my pussy as I walked to my apartment door.
Aaron came in me 5 times in 2 days. If he ever plays Truth or Dare again, certainly not a bad story to tell for the inevitable “How did you lose your virginity” question. I’m all about a good story.
*If you liked this, you may also like my most popular story:* [*Six Close Friends in a Dark Closet [Group]*](https://www.reddit.com/r/gonewildstories/comments/fppy8e/six_close_friends_in_a_dark_closet_group/)
*My chat is open — feel free to say hey and tell me a story of your own.*
Source: reddit.com/r/gonewildstories/comments/jhgjb1/one_small_dare_for_me_one_giant_leap_for_aarons
What a lucky guy!
I want to get that card game haha ?
A long read but hella worth it. Super hot.