A week later school was out for the summer which gave me and Karen a lot more playtime - playtime that often also included Molly. And with Molly, came her strap on. Karen totally adored that strap on and I have to admit I was quite fond of it myself. In fact, I was so fond of it that it wasn't long before I asked Molly to lube it up and fuck me with it while I was pounding away on top of Karen.

Oh fuck. That was such a turn on. I can't really find words to describe it. It was like the first time you tasted chocolate. I came so hard being pinned down against Karen's sweaty body while Molly just kept pounding away in my ass like she didn't care. I came and came again, and so did Karen. Afterwards, me and Karen rewarded Molly by licking her cunt and ass until her eyes were rolled up into her head and she couldn't talk straight, much less walk straight.

---

That summer was one of the best in my life and it was a summer of many firsts, as I think you already suspect. I started to dress up in Karen's clothes more often and more elaborately. Karen taught me how to do make up and walk more girly. She even began calling me Nicole whenever I was dressed-up and made-up.

There was one other thing first though, that also happened on a dare. You have to understand that these dares weren't really a regular thing between me and Karen, most of the time we just screwed around, experimenting with whatever popped into our dirty minds. And they were indeed dirty as fuck. The dare in question was one I hesitated to go through with. I'm sure Karen knew this and that she made a dare of it for that very reason. Otherwise I might not have actually had the experience it lead to. She later told me she came up with the dare after having seen how much I adored Molly's strap on, how I not only loved her fucking me with it, but also loved to suck it too with her riding my cock and Molly straddling my face.

Eventually though, I suggested that we leave Molly out of our games. After that, things weren't as hot between us anymore. Karen even borrowed Molly's strap on once but it was getting obvious that there was something missing. We were starting to slip into a rut and, for two people who have barely been able to keep their hands off of each other, going a whole day without even a kiss was a huge dry spell. Neither of us knew what was going on. Was the attraction of the taboo wearing off? Had we emptied out our curiosity? For a couple of days we barely even hung out.

---

That is until one Friday evening when everything was about to change between us forever. As usual there was a dance thing going on at the youth centre. And as usual me and Karen were outside smoking, sharing a beer, quite bored. At least I was but the smile on Karen's face suggested she had something out of the ordinary on her mind.

“What's on your mind K?”

She killed her cigarette and straddled me. Her hands on my chest pushing me back against the grass. She sat there like that, for what felt like an eternity, looking at me with that wicked smile I both loved and feared. I was getting hard and was half expecting her to screw me right there on the lawn in front of the youth centre. Little did I know what had been brewing in that dirty mind of hers over the last few weeks.

“You really want to know?”

I nodded and at the same time the tone of her voice scared me a bit. It had that seductively evil quality to it, the kind of quality that makes you realise that no matter what you say or do, you are in for a big surprise.

She smiled and started to grind her crotch against mine while telling me that there was this guy from school she had been talking to, about me. Of course the first thought that popped into my head was a threesome with her, me and this guy. At least it was until she told me that he was gay. At first I didn't get what she was suggesting. She leaned close to me, her breasts grazing against my chest, and kissed me.

“I dare you ...”

To describe what went through my head as I finally realized what she was talking about, would take several pages to even give a short description. It's quite safe to say that I was shocked. This was followed by a surge of anger. What the hell did she think she was doing? I wasn't into guys. Our eyes were locked into each other and the tension between us wasn't so much sexual anymore... more a fight for dominance, I suppose you could call it.

I pushed her off me, got up and walked away. I was so angry and a bit offended. I just kept walking. I hated that she had made it a dare. Even though the dares were not a regular thing, in our twisted little minds they were almost sacred. And even though we had never even discussed the price of not completing one, I couldn't get the thought out of my head that I owed Karen one for having walked away.

About three blocks away I started to calm down and, at the same time, the seed Karen had planted in my mind with her dare started to rally sink in.

On top of that, I was, of course, still hard from her grinding against me. I started to remember how much I loved Molly's strap on. Of course, and I think it goes without saying, the step from a woman wearing a strap on to an actual guy with a real cock is huge - first man on the moon huge. At least it was for me.

Two blocks later I stopped and looked up at the stars. I thought about Karen; the excited look on her face when I had asked what she was thinking about, the disappointment when I stood over her for a brief moment between pushing her off me and walking away. I lit a cigarette and turned around. At the time I had not decided whether or not to go through with the dare. I just didn’t want to leave Karen feeling disappointed. We’d been through so much together and, in all honesty, this was our first ever serious fight.

When I got back to the youth centre I found her sitting behind the bicycle shed smoking. Her head tilted forward as if in deep contemplation. As I got closer I heard her sobbing.

“Hey.”

She looked up at me, wiped away a tear and smiled. I smiled back and sat down beside her. I hugged her and kissed her on the cheek.

“I thought I'd lost you,” she said and kissed me on the lips. “But listen Nick. It doesn't take a genius to figure out what the hell it is you are missing. Shush. Don’t speak. What you need is to get fucked real good by a guy.”

I tried to protest, saying that it was different what Molly had done. Karen nodded and agreed.

“Of course it is, but everything we've done so far has been an escalation of our curiosities. We've raised the stakes exponentially over the last six months and this is a natural step for you to take Nick.”

She went on to tell me about how nervous and awkward she had been the first time she had been with Molly, how much she had doubted herself, whether it was right for her or not, how she had almost walked away.

“Yea, sure K, but that wasn't on a dare was it. It's just not fair that you've dared me to do this.”

“No, you're right. I didn't have sex with Molly on a dare. But honestly Nick, aren't you the least bit curious? If you're not then I will call off the dare.”

I looked at her. She was right, as usual. I was of course curious as fuck. I just didn't want to admit it to myself. Neither of us said anything for a long time until I got up. I told her I needed to go to the bathroom and walked off towards the youth centre.

I had an idea which guy she was talking about and as I walked into the café section of the youth centre I saw him sitting alone at a table near the soda bar. His name was Adam and I have to admit that there was something about him that made me want to go over and talk to him, not just as a friend. So I went over and talked to him.

To cut the story short we talked for about five minutes. I told him that I'd never even thought about being with a guy before, not consciously at least. He said that he knew the feeling. We left the youth centre together and headed for his place. His parents were out of town and his sister was at her boyfriend's place for the night. I figured that Karen would figure out why I’d just disappeared when I didn’t come back after fifteen minutes or so.

When he kissed me it felt weird at first, but good weird and soon I was on my back in his bed, my jeans and underwear around my ankles. My cock was rock hard and when Adam wrapped his lips around my cock, it took me fifteen to twenty seconds before I came into his mouth. He just smiled and kissed me, sharing my own cum with me. I was more turned on than I'd been in a long time. And if the first time Molly slid her strap on into my ass was like the first time you taste chocolate, then the first time I wrapped my lips around Adam’s cock was like being shot into orbit around an unknown celestial body. I almost came again just from feeling it throb inside my mouth.

Being a lot more experienced, Adam lasted longer than me, of course. But when he filled my mouth with cum it was like it was the first time I had tasted cum. After the initial blowjobs, we showered together and then shared a cigarette on the balcony. Later we went back in and he showed me his dildo. I smiled as it looked so much like the strap on Molly used. I told him that what I really wanted though was to feel a real cock inside me. He kissed me and took out a tube of lube. He guided me through it all. He lubed me up real good and when he broke my anal cherry I came like a volcano.

I slipped out at around two am to head back home but I was definitely hooked. The rest of the summer I went back and forth between Adam and Karen just as I suspect Karen went back and forth between me and Molly.