I had finally got the opportunity to enjoy some time to dress up. I'm not pretty or passable, but I still enjoy some play time. Black thigh high stockings, pink "Cum inside me daddy" panties and a short black summer dress. Bra, waist cinch, wig and wedge sandals. My pink clitty cage was locked in place, freshly cleaned out and plugged with the largest T-handle jeweled plug in the set. 

Feeling pretty sexy, i set about a few things around the house. Soon though I was horny and craving some dick. I hopped on my favorite sites and started looking at options. Wasn't having much luck, just the usual guys that want to nut in your mouth and go. It was getting late and I was just about to give up. I get a message on one of my sites that intrigued me. Guy several years younger than me but was very interested in crossdressers. I liked what I saw and what he had to say, so we agreed to meet at a park not to far away. Grab my purse with lube and a few things in it and out the door I went. 

I arrived at the park and found a spot I was comfortable with, walking to a nearby picnic table with the cool night air caressing my stockinged legs was a huge turn on. My little clitty was starting to fill the cage out and tighten up. I sent him a message explaining where I was and waited for him to reply. Soon I saw headlights pull in near where I had parked, butterflies kicked in as always. With very little light he found his way to the table and per our agreement, he pulled his shorts down and sat on the bench.

 I immediately got to my knees between his legs and took his flaccid cock in my smooth mouth. He groaned and I could feel him growing in my mouth, caressing his balls with my hand as I started licking and sucking on his cock. He smelled clean and freshly showered which was very nice. Soon he had grown to about 5 inches or so and the head of his cock was very thick compared to the rest of it. I was enjoying licking around the huge head and then taking it as deep as I could in my mouth. After about 3-4 minutes he exclaims, Oh shit! and I feel his cock, which didn't seem to be completely hard, start twitching and he began to cum in my mouth. I swallow every drop and really enjoy the salty taste of his cum, it's the kind of taste that stays with you for hours afterwards. 

Apologizing profusely for cumming so quickly, his face was red and he was ready to walk away. I asked him if he had enjoyed it, to which he replied, yes very much. I assured him it was ok and that if he wants to try again in a few minutes we could. I  asked if he would like a beer as I had a few in the car. "Sure" so we walk to the car and I grab us a beer, hoping to take the edge off a bit. He chugs it nervously and I hand him another. Sipping the second one we decided to walk to a little more private spot. 

As we are walking along he steps a little closer to me and I feel his hand on my butt. This was new to me but I definitely liked it and scooted into it a little more. A few more yards and we found another table that was suitable away from prying eyes(or so we thought, but thats another story). We sat down sipping the beer and I lit a cigarette and leaned back against the table. He placed a hand on my stockinged leg and slowly felt along the length of it. Soon he head inched his way up to my panties and was feeling my cage through them. Getting aroused again I finished my beer and cig, asked if he was ready to try again. "Yes" he says still feeling of my stockinged legs. 

As he pulled his shorts down and I resumed my position on my knees, I noticed that he was half hard again. I start licking sucking and fondling his balls which seemed twice as big as they were earlier. His cock starts growing and growing, much more than it did the first time. I guess the beer relaxed him enough. Soon his cock was about 8 inches long and that big head had become huge! I was beginning to worry about it fitting inside me. It completely filled my mouth and all I could get in was 3 inches or so! Throbbing hard now, I asked if he wants to fuck me. "Yes, yes please " he says. 

I stand and hand him the lube I brought, lean over the table and wait. He gets behind me and I feel his hands on my ass, rubbing and squeezing. I wiggle against him a bit, anticipation for what's going to happen. He flips my dress up above my panties and I hear him say how fucking sexy those pink "Cum inside me daddy " panties are. He runs his hands over my ass a few more times and then pulls them down to my knees. I hear the tube being opened and closed. Reaching back I pulled out my plug and laid it down. One hand on my butt I felt him start rubbing that huge cockhead between my cheeks.

I asked him to be gentle at first as I've never had anything that big in me. Slowly he finds my hole and starts pushing, I breathe deep a few times and start pushing back against him. Suddenly the head pops in and a sharp pain goes through me. I gasped and he stops, asking if I'm ok. Yes I'm ok, just give me a second to adjust. I take a few more relaxed breaths and start easing back on his cock. He takes the hint and starts pushing it in me slowly until his balls were against me. By now I am excited and it's starting to feel great. He starts sliding out and back in, taking his time. 

I whisper over my shoulder "fuck me, use my sissy hole and fill me with cum". He picks up the pace a bit and soon he's ramming that 8 inches balls deep with every thrust. I'm moaning and groaning like a cheap whore, enjoying every thrust of his cock which is absolutely rock hard by this point. His hands are gripping my hips, the cool night air on my bare ass and stockinged legs feel amazing. He slows down and speeds up, some long deep strokes, some short and hard. After about 15 minutes of this he tells me he is going to cum. I tell him to do it balls deep in me. A few more seconds and his grip tightens on my hips and he slams his cock deep as possible. I can feel it throb and swell as spurt after spurt fills me. He stays deep until his cock starts to soften, I grab the plug as he starts to pull out and immediately shove it in and pull my panties up.

I asked if he was glad he stayed for round two. He said yes and asked if we could do it again sometime. Sure, I replied as we walk to our cars. I could feel a few drops of his cum making their way past the plug in my ass, running down the inside of my thighs. Pure bliss in my perverse mind.