I had mentioned this trip to several people in PMs, but I've never published it...until now. This trip was in fall of 2016 and was an amazing experience...it was also in the days of Craigslist...man I miss Craigslist. There were three wild nights to this trip. Part I The Booth & The Park, Part II The Dom Room, and Part III The Breakdown.
First Night, Part IA -- THE BOOTH
So...I have a trip to San Diego planned for work. A few days before I'm due to travel to San Diego. I post an Ad in Craigslist. I was still fairly new to exploring Roxy's submissive (and slutty) ways but thought this the right opportunity. I posted an ad looking for Alpha/Dom Men willing to help push me along this road I was starting to enjoy so much.
After sorting through the usual CL piles of garbage replies ("Still Lookin'?" or "Hey!"...do those EVER work by the way?) I start corresponding with a few guys that seem promising. There are three who are most promising. First, was a guy who said he would only take me under very specific circumstances; another with a cool fantasy about my car "breaking down" near his house; and a third who said he'd take care my whole evening for me and mentioned much of what I wanted to experience, he was interested in helping with. Part I is about #3, as he was my first night in town. I will come back to the other two.
Guy #3 tells me to call him "Mike" [I never want to know real names...I value discretion!]. We agree to rules, limits, boundaries and fantasies...but no spoilers, I'll leave those for you to learn as the night plays out...
Finally the time comes for my trip. I arrive in San Diego and check-in to the hotel where my co-workers are staying. We meet for an early dinner. I grab my Roxy "go" bag and head to something more non-descript and with exterior access in Mission Valley. I text Mike and let him know I'm there. I shower, shave, trim, clean up, and start working on make-up.
There's a knock. "Mike?" I ask? "Yup." I look through the peephole -- youngish (30's) dark hard about my height (5/10) and HWP. Cool. I let him in. I have laid out all my clothes on one of the beds for him to choose from. He picks my black lace-up corset, tiger-pattern bra, brown pleather micro mini-skirt, fishnet stockings, garters, black long curly wig, see-through blouse, and my 6" patent leather locking ankle-strap fuck-me pumps; pretty much exactly the outfit I would have picked. He tells me to plug my ass-pussy and leave it until he tells me otherwise. He tells me to put on my studded leather slave collar and he takes the leash.
He asks if I have a cock cage. I say "no." He smiles and says, "no problem, we'll fix that first."
We leave the hotel and walk to his car. We drive about 10 minutes to an adult store off Pacific Highway. He pulls up front and tells me to get out and go inside and ask about cock cages. He will be waiting in the car in the back parking lot. I do as I'm told and this pretty hot punk-looking girl is happy to help me. We decide on a clear acrylic cage. There are a couple of guys in the store and one has looked at me several times. I take the cage and leave the store. I walk around to the parking lot and as I approach Mike's car I see him talking to another guy. They look at me and the guy pauses and says, "ok." He heads into the store.
Mike tells me to get in the back seat and put on the cage. It takes a while, but I get it on. Mike locks it and puts the key on his car key ring. He tells me it comes off only after I've done everything he wants me to do. And if I fail, he will throw away the key. I'm not sure whether he's joking or not, but I'm excited. He tells me we're going back in and I'm going to go into one of the video booths with the guy he was just talking to. I'm not to speak unless spoken to. I am to give him a blow job and make sure I swallow every drop. I love the assignment, but I'm nervous about the risk. He says he will keep a watch in the store but it would help if I tipped the clerk $20. We walk in, he looks at the clerk, she flashes some fingers and, after I hand her my tip, we walk toward the back. At the entrance to the booths, he tells me 2nd curtain on the left and don't come out until he comes to get me.
I walk into the dark video booth and the parking lot guy is there watching str8 porn. It's a 3-some scene. His cock is already straining in his pants. I get down to my knees and pull down his shorts. I take his cock in my mouth and he immediately starts thrusting. It's maybe 5" so I have no trouble taking it...and of course, I'm loving it. The smell, the taste, the feel of a really horny guy who wants to fuck my mouth is why I started dressing in the first place. I work his balls and ass and he grabs my head and forces it down on his cock. Mmmm...I feel it stiffen and he shoots into the back of my throat. I lick him clean and he leaves.
I sit back for a few minutes enjoying the warm satly gooey taste in my mouth and another guy walks in. He's about 6' and maybe 50ish. He puts his hands on me to get me to my knees and tells me to make love to his cock. He's already pulled it out. I work it slowly, taking his balls into my mouth, and get his cock wet with my drool. I couldn't wait to taste him. I keep working him and then sucking on his balls. He moans and grunts every time I work his balls. When I take him back in, he starts to face-fuck me. Mmmmm... My clitty cock was starting to strain and hurt in the cage.
The guy pulls my head as far as he could...I feel his cock in the back of my throat and fight the gag reflex as I know the pleasure is soon to cum...and it does...a LOT! "Now, suck him off" he says and turns to another guy I hadn't seen come in the booth. He spanks my ass. It startles me. And my cock was in pain.
He does it again.
I start working the other guy's cock. This one is all of 7" and thick. He responds better to the softer work of my mouth. After a bit, I could feel he was close, but he looks and me and says, "uh-uh, I'm going to cum on your face slut." I smile and keep working his cock. He reaches down, takes hold of his cock and cums on my face, wig, and chest. A lot. Once he was done, I cleaned his cock. He told me, "Mike says to leave it and come out now. Oh, and see you later."
I'm a gooey slimey mess and smell like cock, balls, and cum...basically a pretty happy cum-slut. I walk out of the booth area and Mike is nowhere to be seen. The clerk looks at me and smirks. "He's in the parking lot, said to tell you to meet him there. Just like you are. Fun night?" I smile, "oh yeah!" "Cool," she says.
I walk out and around to the parking lot. Mike's in his car. He points to the back seat. I get in, "don't get cum on my seatbelt you fucking whore. And do not even think about wiping any of that cum off your face." I don't buckle up. He starts the car.
First Night, Part I-B -- THE PARK
Mike drives about 15 minutes to a park somewhere near some water. H pulls over and says, "Alright, you are going to get out here. Then you are going to take your slutty whore ass and walk to meet me on the other side of the park. You will not wipe the cum off your face, dress, or body. You will do anything any guys you meet tell you to do. Now get the fuck out!"
He points. There's a path that leads through the park. He hands me a pack of cigarettes with only a few left and a lighter. "Walk until you see a park bench and then stop and light up. I will be nearby. If somebody happens to rape your sorry ass, I won't stop them."
Again, not sure if he's kidding or not...and it's exciting and terrifying at the same time.
I get out and start walking. As my eyes adjust, I still don't see any people around. My spikes clicking on the pavement, I work my way toward the other side of the park. I love walking in 6" heels...how it makes my legs look, how I have to work to keep my balance, how my hips shift like a woman's.
I don't see Mike anymore. As I get closer I see a few guys hanging around a park bench. They're talking and looking at me. I still don't see Mike. I light up the cigarette. One guy walks up to me and looks me over.
"You look like you've been having some fun," he says.
I smile. "Some," I say.
He steps in closer, "Is that what I think it is?" he says and points to the dried cum on my face. "I've got a lot more if that's the kind of slut you are." I look at him, blow out a puff, and say, "Why don't we find out?"
He reaches under my skirt and feels my caged clitty.
"She's caged!" he shouts!