Allen came downstairs from taking his shower, he was naked and reached for his shorts.
"Wait," I said, "You won't be wearing those."
I beckoned him over to me, I placed a cock ring around his cock and balls, snapped it into place.
"I love these!" He said, as I stroked his hard cock.
I then handed him a t-shirt, plain, black, with no logos or emblems. He slipped it on. I then handed him a black skirt, yes skirt!
"Uhh...you want me to wear a skirt?" He asked.
"Yes, but I'm not cross dressing you, just trust me, this will make it easier for us to play later."
He took the skirt and slipped it up his legs. The skirt was elastic and fit snug around his waist. It was very short, barely covering his butt, and with his erection, the front wasn't hiding much of anything.
"Now, that looks pretty hot," I said, "turn for me and lift the skirt as you do."
He did, stopping with his back to me, the skirt exposing his very cute, white butt.
"Perfect, now bend over," I ordered. He did as I said and I took a lubed, metallic butt plug and inserted it into his ass. He groaned as it entered him. The hot pink jeweled end was held in place by his butt cheeks.
"Oh man, I don't know, with the cock ring and the plug, I might cum really soon!" He said, standing and rubbing his naked butt cheeks, massaging them together.
"If you cum now, that's okay, you'll just have to lick it up."
We both smiled. I led us out to the garage and we headed to an adult video store that was about an hour away. While Allen was cleaning up, I posted an ad on CL with a picture of him sucking my cock. It was from above, so you really couldn't see his face. It was a simple ad, 'Wanna get sucked by a twink college boy? Be at the AVS on Winslow at 5'.
We went through a drive thru to get something to eat and drink for the long ride there. Allen was bit nervous, wearing the skirt which you could plainly see across the car from their service window.
Once the girl handed us our food, she leaned down low and said, smiling, "That's a really cute skirt, I have one just like it."
I lifted the skirt so she could see his cock, the erection had subsided some, but he was still semi-hard.
When she saw what was under the skirt, her eyes went wide and she smiled even bigger and said, "You should come back again real soon, I'm sure we could have fun with that!" She then stood back up and said, "Thanks again, have a great day and come back soon!"
"Wow, I think she wanted you!" I said.
Allen was blushing and replied, "I know, that was kinda weird I mean with me in a skirt and all."
"Gotta love kinky girls my friend, she would probably do anything you wanted her to do."
He nodded, "yeah, probably more so than Wendy, she's not kinky at all!"
We both laughed and headed out. After he finished his burger, I slid my shorts down and told him to suck me. He got into the seat, his ass in the air, leaning over and taking my cock into his mouth.
As he sucked, I made sure to pass several cars that could easily see into our car and see his naked ass, skirt around his hips and the pink jewel of the butt plug. Several trucks sped up to get a better look and even blew their horns.
Just before we arrived at the AVS, I came down Allen's hot throat. He swallowed every drop and kept sucking until I had parked the car. There were only about five cars in the lot, but was still early and this place didn't get really busy until around 8 in the evening, it was only a little past six.
Allen sat up, wiping his mouth on the back of his hand, smiling he said, "Man, I love your cum, I could drink it like that all night long."
I grinned, then said, "Okay, here are a few rules. No one will fuck you, unless you want them to and then only with a condom." He nodded and I went on, "You will suck cocks from two sides, we'll be in room Five, there is a hole on each side. The holes are big enough for an ass to come through, that's why I said if you want to get fucked, you can." Again, he nodded, "Once we go in, I want you to walk around the store, especially into the gay/bi area, there's a big sign hanging there so you can't miss it. If there are guys over there, I want you to lift your skirt and show them your cock and then turn and show them your ass." Again, Allen nodded, his cock back at full size now.
I went on, "Once you think you have had enough, we can stop, just tell me. There may only be a few guys, there could be a few dozen." Again, he nodded.
"Okay, let's go," I said. We got out of the car, the light breeze lifted his skirt, showing his naked, white ass. The front of his skirt stuck out due to his erection.
After we got inside, I stopped at the counter and spoke with the girl working the desk. I explained what we were going to be doing and told her to direct anyone that came in to the booths on either side of booth five. She agreed, then she looked Allen up and down.
She was cute, with purple hair, a nose ring, nice titties in a fishnet top and black bra. Her skirt was very short, almost as short at the one I'd made Allen wear, and she had black fishnet stockings on, with black tennis shoes.
She smiled at Allen and asked, "Do you do girls too?"
He smiled back and said, "Of course, I'd be happy to do you."
She smiled and asked, "Full service?" He looked puzzled by the question, then she added, "You know, fuck my pussy. eat me to orgasm?"
He grinned really big now and nodded, "absolutely!"
He then walked off to the gay bi section, I could see there were three people over in that area, two men and one woman. They all looked to be in their forties. Allen did as he was told, flipping his skirt up, showing the couple his ass and cock first, then moving to the single guy.
