The morning sun began to filter into the room waking us up. We all woke up 3 very naked and happy people. Regina got out of be to freshen up first saying "I'm really hungry, we never had dinner last night."
"Sounds like a real good idea. I am hungry."
So we all freshened up and headed to the quaint little café around the corner. We were seated outside which was real nice. The street was separated from the dining area by an ivy covered wall. The setting was very small and intimate, perfect for us. Our waiter shows up and he is wearing tight running shorts and a tank top. Only in Key West. He was extremely friendly while taking our order and I'm pretty sure he gave us a knowing wink as he left.
We sat and had a wonderful breakfast while we chatted away. Not much was said about the sex at this point. But that didn't stop me from rubbing their legs under the table. In fact at one point ran my hand up Jerome's leg and under the leg of his loose shorts. He wasn't wearing underwear. This made me smile.
Finally I broke the ice by saying "so what's on our agenda? Do you guys want to find something to do or just go back to the room for more sex."
Regina replied "there's a few things I'd like to take back to the room like water and maybe some snacks so why don't we walk the street and do a little site seeing first."
Sounded like a good idea and off we went. Duvall Street has many interesting sites if you enjoy people watching. What made it entertaining was that no one seemed to be inhibited. Everyone was very comfortable in their shoes and looked very happy. We ambled along checking in to a bar every once n a while for a drink. As we were walking down a side street we came across and adult toy shop. Now normally this would not be Regina's thing but she was open the the suggestion to go in and check things out. "Maybe we can find something for us to have a little more fun with." And with that we went in.
It had plenty of magazines and very few VHS tapes as VHS was still relatively brand new. It had a lot of toys. I had never had nor used a cock ring before and I was very curious about trying one. As I was studying the packages I heard Jerome say "Oh man, look at these!"
I went over to where he was standing and saw a wide variety of dildos and strap-ons. "You think Regina would try one of these out on us?"
We gave each other a knowing look and a mischievous smile.
"Hey honey, come here and check these out" I said. "With one of these we can all take turns getting spit-roasted. What do you think?"
She looked a little apprehensive at first but then broke into a smile and said "Oh what the hell, why not. We're here to break some barriers. In fact I was over there looking at some cock rings. What do you think?" She led the way and I was amazed at the way she has embraced her new found sexuality. "I think this leather one would look very sexy on you. Let's get it."
"We should get one for Jerome, too. Is there any one there that you like?"
"He smiled sheepishly and said "I actually like that pink one there." We all laughed at that and grabbed it.
We browsed the store a little more before we checked out. We left with the leather cock ring, a pink cock ring, the strap-on and a tube of Astroglide. We walked the streets a little more but I think our purchases were begging to be used so we made our way back to the room.
Once inside the clothes came off very quickly as we started running our hands all over each other. I gently moved my hands behind their necks. I leaned in and planted a kiss on Regina's lips lightly using my tongue on hers. I then turned my face towards Jerome and gave him an open mouthed kiss bringing out moans from the both of us. Jerome then leaned into Regina and gave her a kiss.
"I want to see you guys wearing your cock rings" Regina purred. "That would look so hot."
"Sure. In fact, why don't you put them on us" as I Led Jerome to the edge of the bed where we sat down. Regina reached in the bag and pulled the cock rings out. Leaning back to give Regina some room to work as she grabbed my cock and slipped the ring on. Then she grabbed Jerome and slipped his on. Then she bent over and took him in her mouth while stroking me. She likes blowing Jerome more than she likes blowing me because she has a smaller mouth than most and can handle his a lot easier than mine. It didn't bother me at all to see her going down with such enthusiasm. We looked at each other smiling broadly. Jerome was enjoying it as he tilted his head back and let out a very satisfied moan. She bobbed her head up and down a few times then pulled him out of her mouth and said "oh no, I can't let you cum yet. we have another toy we need to break out." as she reached bag into the bag and pulled out the strap-on.
"Give me a second so I can figure out how this thing works. I've never used one before." She examined it and took a minute to figure out but soon had it in place. Once she got it on she had a proud and playful look on her face. She grabbed the dildo and started to stroke it saying "I can see how you guys like to do this. It is very sexy. Who wants to be my first?"
Jerome said "well, Jim fucked me yesterday so I have to think it's his turn."
I gulped at first. I've played with my ass before but never anything this big. It was intimidating. Jerome saw my apprehension and said "don't worry, I know how to make it easier for you. Let's use these fleets and get cleaned up inside first." Even using the enemas had a bit of eroticism to it. We cleaned up inside and stepped into the shower. With each of us having a bar of soap we washed each other down. Every now and again kissing and rubbing a cock. When we were done we stepped out and grabbed a towel.
We walked back to the bed and there was Regina looking oh so ready. It was at this point that Jerome stepped up and took over.
"Go ahead an get on all 4s on the bed" Jerome ordered. It was a nice change of pace to have someone telling me what to do. He started rubbing my left ass cheek as he turned to Regina and said "let me have some lube on my fingers. Don't worry Jim yours is certainly not the first ass I've broken in" as he took his other hand which had lube on it ran it up and down my crack pausing every time he was over my hole. Every time he paused it caused me to take a sharp breath. Then his fingers started to linger over my hole. I was rather relaxed now as his first finger made penetration.
He had me so relaxed that his finger slid in easily. He quickly added a second finger and was pumping slowly away. It felt real good to me at this point and I wanted more. I guess he sensed this and slid a third finger in. I let out a long "mmmmmmm" as he massaged my hole.
I heard him say "he's ready for you now. If you feel it getting dry feel free to add more lube, OK?" he said as he withdrew his fingers. It felt like a momentary let down until Regina lined the dildo up to my hole. She slowly applied pressure as the the lubed up phallus was pressing against my hole. Then I felt it slide in which caused me to take in a deep breath.
"You OK?"
"Yeah, you're doing good. Just go easy to start, please."
Regina was good about taking her time with me. With every push she would go a little farther. I was getting more comfortable as she started to get a rhythm going. I reached over and grabbed Jerome's cock which was the sign for him to move up to the head of the bed and position himself so that I was between his legs. I wrapped my hand around his pecker with a "hell yeah" and started to stroke it. I was staring at his beautiful cock intently as his precum started to seep out. I suddenly realized how hungry I was and how much I wanted him in my mouth. I flicked my tongue over the head first tasting his juice. It was intoxicating. I slid him into my mouth first taking his head moaning as I was savoring the taste and the feeling.
This prompted Jerome to give out a guttural moan as he was exhaling. Watching this must have turned on Regina because she started pump me faster and harder. This made me go farther down on Jerome's cock and suck a bit harder. We were basically feeding off each other. The more one of us reacted the more the other 2 gave. I was getting pounded pretty good by this point when I heard Jerome say "oh that feels so good Jim. You're gonna make me cum. I'm gonna cum soon. Do you want me to cum in your mouth? Do you want to swallow my load?"
