Chapter 3: Awkward Challenges

Sunday morning, about ten a.m., I answered the knock on my door. Sheri was there with a smile. “Good morning, Sunshine. How’d you sleep?”

“Fine, thanks to you. I was so nervous last night with those men.”

“Honey, you did fine. You bought a bicycle from Luke, and chatted with Owen, and danced with all three men. You kissed them, too; and I know that was a big step. You didn’t have to fuck on the dance floor. That was a big step for you. You did well. The next time it won’t be near as stressful. I watched you, and you seemed quite calm.”

I laughed. “It was a façade. I was monkey brain inside my head. How did the evening end?”

Sheri said in a nonchalant way, “We went back to Luke’s apartment because it was nearby. Maryann and I fucked the three of them, and I mean that each of us fucked each man, so no one was left out and uncared for.

“We slept there on some futons that we spread out on the floor. I slept between Sean and Owen, and also fucked both of them in the middle of the night. I did Luke this morning as Maryann took on the other two.”

I gawked. “You fucked them!” I was almost horrified. They hadn’t known most of the guys we’d all met for the first time the night before.

“Yes. They were nice and we wanted to make friends. We all traded numbers and promised to get together again.” I sighed, kind of glad that I hadn’t had to confront that kind of situation ... yet.

“Did anybody say anything about me?”

“Yes. Everyone wished that you’d stayed and participated, Owen especially wanted to fuck you, but so did the other men. I told them more about your background, and how we were grooming you to be one of the busiest sluts on the coast – but I told them they’d have to wait a week or two for you to warm up to the idea and do some homework in that direction.”

“Oh, God. Luke is coming by this afternoon with the bicycle I bought. He’ll expect me to jump in bed with him.”

“He won’t expect you to do anything, so don’t worry. Just buy the bike, and maybe take a short ride with him. Now, about your mode of dress. What will you wear?”

I looked down at the shorts and t-shirt that I had on. Sheri shook her head. “Nope, not sexy enough.”

Sheri helped me pick out the Daisy Duke shorts and my new crop top that showed all sorts of under boob. Fortunately, according to Sheri, I did have luscious boobs. “Wear these, and sneakers; that way, you can ride the bike and not worry about heels. Normally, you’d wear your new four-inch heels with this outfit to make yourself available and fuckable, but since you’re getting into a new sport, today is different.”

I rolled my eyes, but under her gaze I stripped and redressed.

I’d no sooner finished, that my phone rang. It was Luke asking about a good time to bring the bicycle by. We decided that one-thirty was good. He asked, “If I bring my bike, can we take a short ride?”

I had him on speaker and Sheri was nodding wildly to me. I said to him, “Oh, yes, that’d be good. You can show me about shifting or whatever else I have to do to ride it well.”

Luke ended the call. Sheri praised me for accepting and then gave me a lecture about behavior, including how I was to kiss him ‘significantly’ to thank him for delivering the bike and teaching me how to ride it.

She said, “I know you won’t fuck him, but if you get a chance put his hand under your crop top and let him get some thrills playing with your beautiful tits. Start to build a relationship with him, too. Maybe even go on one of those long bicycle trips with him after you’ve built up your ability to ride that far.”

“That’ll take practice so I have muscles and don’t get sore.”

“I told you that you needed a sport. Now, you’re starting to see how it relates to your interaction with a member of the opposite sex and probably a whole group of other people that share a similar interest. Get into the sport both physically and intellectually.”

I promised I would.

Sheri left promising to see me at work the next day. I went online and downloaded a copy of Zen and the Art of Bicycle Touring. I’d read most of the book when my phone rang. Luke was outside with my ‘new’ bicycle.

Luke spent twenty minutes with me teaching me every part and nuance of the touring bike. He helped me adjust the seat. I was sure he got more than a glance at my pussy barely hidden in the Daisy Duke shorts, and I know for certain he could look up at me from his seat on the ground as I sat on the bike and see my complete set of boobs in the crop top.

I found myself fascinated with the man who had fucked both Sheri and Maryann multiple times the night before. I think I stared him in wonder many times during his visit, trying to visualize what the sex must have been like with the three men and two women.

Luke had included a front handlebar panier that carried more than a large purse, and a water bottle holder and new bottle. He loaned me a chain and lock, and I promised to return them after bought my own. I gave him a check for the bike.

We went on a ride. I was amazed at how easy it was to ride and learn to shift. The last bike I’d ridden was over ten years earlier. It was a one-speed bike, and we lived in a hilly area. I knew how to ride but hadn’t ever done it for fun. This was much easier, especially with the various gears.

He led me along some local roads with bike lanes out to the beach. Once there we parked the bikes and just looked out at the surf and the people walking the beach for a while. Far off-shore there were two wind surfers speeding to and fro on their surfboards with their kite-like sails propelling them along at a rapid speed. Occasionally, one would leap out of the water, going maybe twenty feet into the air.

Luke said, “If you’re interested, I could teach you how to do that someday, too.”

I grinned, “I think I’d like that.”

We rode back to my apartment and he helped me put the bike in the storage shed and lock it up. We talked about taking a longer ride. I was surprised when he told me that we’d just ridden about twelve miles roundtrip. I didn’t think I had that level of endurance.

Luke presented me the key to the lock, and I presented myself to Luke the way Sheri had recommended. I plastered myself against him, and kissed him on the lips. He was delicious and tasted minty. I took his right hand and slowly pushed it up from my bare belly up to my bare boobs under my crop top. We kissed some more. My heart rate topped out at about a thousand beats a minute. I felt my body temperature soar. Brain fog immediately descended on me, and I had arousal like never before.

He smiled and pawed at me until he had both of my nipples standing up at attention. He bent over, nudged the fabric up, and then sucked on one of my breasts. I flushed and could feel a flood of female fluids in my pussy. Oh, fuck, I could even smell myself.

We kissed some more, and then Luke excused himself, bid me good day, and left. It was all smooth and pleasant. I really liked him. He was a fun guy. I wanted to see more of him, even if he had fucked Sheri and Maryann all night.

Once he’d left, I went back inside. I was so horny. This was a unique feeling I’d rarely felt before. The kissing and Luke’s fondling of my breasts had been really ... sexy. I was turned on.

Sheri had told me that when I felt like this I should ‘jill off’ – masturbate. I’d done that a few times over the years, but now I suddenly saw the real need for that activity.

I took my top and shorts off and lay back naked on my bed. Propping myself up with some extra pillows. I used my two hands to play with my pussy, trying to duplicate what Maryann and Sheri had done to me the morning before. God, that seemed so long ago.

I finally found that manipulating two fingers from my left hand in my vagina, as I used three fingers from my right hand to massage my clitoral area worked perfectly. I toyed with myself for twenty minutes, edging myself up and down several times. Finally, I could feel something building.

My orgasm hit me hard. I ended up doubled over on my side with fingers inside me as a cannonball of pleasure punched through my body. God, what a great feeling. I should do this more. I’ll ask Sheri whether she masturbates.

I realized that as I been jilling, I’d thought of Maryann and Sheri fucking the three men we met at the lounge the night before. They’d thought nothing but eagerness at going someplace so they could make love. Further, each girl had fucked all three men, in some cases multiple times. That situation was very arousing and helped drive me over the top. I wished I hadn’t felt so timid about such a sexual situation. I wanted to fuck three men that I’d just met.

I realized that with a simple sentence or two, I could have invited Luke in and fucked him that afternoon. God, I was still horny.

I realized once I went to eat dinner that Sheri had left me a handwritten note. I opened and read the note. Sheri had given me instructions for that Sunday night. Fundamentally, I was to read several specific stories on a couple of websites that specialized in erotic stories, and then I was to watch at least four online videos that showed ‘perfect’ blowjobs being rendered. She gave the websites and told me what to search for to find the right videos.

I made a dinner tuna salad, and then opened my laptop to eat in front of it as I read stories or looked at pornography. I was nude. After finishing dinner, I moved to my sofa with the laptop. When I started watching the videos, I moved the laptop slightly to my side so I she could play with my vagina and clit some more. I was very wet.