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A Trip to The Park

By: VTDarkAngel



With Jesse gone, I didn't know what to do. I felt abandoned and lost, not wanting to do anything at all, especially study for my one last exam of the school year, which was still almost a week away. Before long, I began to think back on the fun we had in bed and, despite its scarcity, how good it still made me feel. It didn't take much time before I began to feel better than I thought, and I began getting aroused. Not wanting to let a perfectly good boner slip away from me, I decided to make the best out of it. I closed my door, locked it, and sat down at my desk. I slipped my panties off and began to rub the outside of my skirt slowly. I couldn't resist myself much longer, and I pulled my skirt up and began stroking my now hard cock.

As I continued to stroke, I slid my index finger and middle finger into my pussy, as well as my ring finger and little finger into my butt. I leaned back slightly, and kept at it until I managed to have both my orgasms, with my cock cumming first, then my pussy. What a mess I managed to make. 

I found it in my best interests to wander off to the shower and clean up after myself. It felt slightly awkward, knowing what I had just done, but also I felt slightly reassured that nobody really knew and, even if they did, that they wouldn't care as we'd all be moving out shortly anyway. 

Feeling quite refreshed from the shower, I pondered what I should do with the rest of the day. I remembered that one of my friends had told me about a nightclub in Roanoke that featured drag shows on Sunday nights, and I decided that I'd go. Even if I didn't meet anyone, I figured that I'd at least manage to get some entertainment out of it. After all, as little of a fan of guys as I am, when I see a guy in a skirt, or dressed up like a girl for that matter, I tend to get a little excited.

Despite the fact that I didn't expect to find anyone nice at a nightclub, I decided to break out the black nail polish and lipstick, which I didn't bother with very often, but I did keep around for occasions like these. For some reason, I got carried away and wound up painting my toenails as well as my fingernails, which was rather pointless since I'd be wearing ankle-strap shoes that didn't show my toes, and I didn't figure I'd be taking my shoes off for anyone. Once the polish dried, I went to the closet to pull out a velvety black dress that came down to the floor on me, which almost forced me to wear heels. After looking at myself in the mirror for a minute, I put my choker around my neck. For some reason, I treasured this one accessory, despite the fact that almost nobody else besides me liked it. There were a few charms that I had that I would wear with it, albeit not at the same time. There was the cross, which I wore when I'd go to church, as surprising as it may seem. Then there was the heart, which I wore when I felt all mushy and sought love. The one that I most often wore, and the one I wore on this night, was the bat, which most folks described as a stainless steel likeness of me, because I was usually a nocturnal creature who would randomly fly around and who everyone else thought would bite. 

Noticeably absent from my outfit was any form of undergarment. I didn't want to bother with such, especially when I was on the prowl for some fun. After all, they'd be just one more thing to get in the way. As I got ready to leave, I pulled my little purse out of the closet and loaded my keys, my wallet, and other various necessities in it. I turned the lights off and closed my door behind me, hoping to have a nice quiet trip when one of my neighbors noticed my exit. "Hey Morticia, where ya goin'?" 

I spun around and shot a look towards her that could kill a person, "I'm going out to try and scare up a little fun... wanna come along?"

My neighbor looked incredulously at me, shying away slightly. "No, not tonight. I'm sure you can scare enough people without me."

Batting my eyes flirtatiously at her, I replied "I know, but still, the more the merrier." With that, I turned back around and walked out of the dorm to my car, a good half mile away. 

I suppose it went without saying that I got some strange looks on that walk, even from the police officers who were driving around at that hour. I guess I was an odd sight, being the only girl who would dress in all black in May. Perhaps I wouldn't stand out so much in a nightclub. Ok, so maybe I was wrong.

When I got to the club, I handed the lady my purse and I walked on in, hoping to find somebody to latch on to. There were quite a few folks in there, but few that really grabbed my attention. I could easily tell that every drag queen there was at least twice my age, and there weren't many single college-age people there. I noticed a cute girl who looked quite boyish, and she reminded me vaguely of Jesse when I first met her. I greeted her, and we talked briefly, but she excused herself by saying that she was going to where her girlfriend was. 

As I made my way through the crowd, I could see that there wasn't much hope for me, as gay guys outnumbered everyone else three to one, and I seriously doubted that I could turn a gay man straight. I walked outside onto the deck, where folks went to chill out and take it easy. I found an empty spot on the bench and sat down, feeling slightly alienated due to not knowing anyone there. For some reason, I briefly looked up to see someone in a short black skirt and high heels walking around inside. I quickly got up and attempted to find this girl. While I searched, my mind wandered and I began to get aroused. Not finding her upstairs, I almost ran downstairs and almost ran into 'her.' I could quickly tell that this person was a guy dressed as a girl. Laying aside my manners, common sense, and inhibitions, I simply put my arms around him and gave him a hug. It took a second, but at least I felt his arms wrap around my back briefly. 

"W-w-what prompted that?" he stuttered, slipping into his male voice.

"You look sexy as a girl," I whispered in his ear.

"Why, thank you," he responded, trying to sound more girly. "I heard it was drag night, but I didn't realize there'd be so few people actually in drag."

Shrugging my shoulders, I pondered, "Maybe it's an off night for some of 'em, but still you're really cute. Your voice could be worked on a wee bit, but you're still relatively convincing."

He began to blush, at which point I grasped his hand gently, leading back down the stairs to a relatively quiet spot. I could see the confused look on his face as he knew that I had something in mind, but he didn't know that I had something extra under my dress for him to play with.

In the corner booth, I slid in next to him as he awkwardly slid over next to the wall. I had him trapped, but I somehow suspected that he didn't want to go anywhere. No, he was going to be mine for the night. I could see that he was very nervous, and I tried to calm him down with a little small talk. He confessed to being bisexual, which was quite alright by me. I also found out that he went to the same college as I did. At that point, I knew that he had nowhere to run. 

I inched myself closer to him, and could tell how nervous he was. He stuttered, "I think I gotta go to the bathroom." 

"Nonsense. You're just nervous 'cause you know I wanna kiss ya, cuddle ya, and take you home with me," I retorted, putting my hand on his smooth face. I could see him blush in the dim light as he tried to draw away, but I knew he secretly wanted to be kissed. After all, why would he dress in such an outfit as he did if he weren't looking for action?

I pressed my lips against his, although his lips were still sealed. I slid my tongue piercing between his lips and gently pried them open, sliding my tongue between them, and was delighted to find that his tongue was pierced just like mine. Before long, his hand reached up for my cheek and he began to relax as we continued to kiss. My hand slid off his cheek and down his neck to his shoulder, then to his chest, which had been padded rather well to resemble a respectable female bust. With our hands gradually sliding downwards, I began getting harder as I wondered just how far he'd go. My hand lingered for quite some time at his waist, then softly rubbed his stomach. I nervously moved my hand down on the outside of his skirt and felt a slight bulge beneath it. Instead of trying to get him off while still inside the club, I moved my hand away and continued to kiss him, deciding to wait until later, then totally surprise him. After what felt like an eternity, our lips finally parted and I could tell that he was starting to tense up again. 

"Now that wasn't so bad after all, now was it?" I inquired, in an attempt to get him to want me.

"No it wasn't," he giggled, trying to be girly. "It was the best kiss I ever had."

"Good. You actually kiss like a girl too, ya know."

He blushed again and tried to hide it. I could tell that he was enjoying himself, and I could also tell that he was trying not to touch himself in front of me. As his hand wandered down towards his waist again, I took it in mine and got up, leading him upstairs and eventually out of the club. When we got to where we were parked, which was off to the side of the building in an out-of-the-way spot, I decided to quit teasing him and have some fun. 

"I noticed that you were gettin' pretty turned on in there, eh?" 

"Hehehe, yeah, I was. I-I-I couldn't help it," he stuttered, trying to avoid the subject.

"Oh, that's quite ok," I assured him, moving my fingers slowly towards his waist again. "I'm sorry if I was being a tease in there. I think I know of something that would be much better than teasing though."

With that, I reached up his short skirt to find a pair of lace panties, which I promptly pulled off. As they fell down to his ankles, I squatted down and began to hold his cock in my hand. His cock was actually smaller than mine, but at least I knew that it wouldn't overwhelm me. It felt so good to hold somebody's cock other than my own. I began to gently stroke it, and could tell that he had been hard for quite a while, as some precum began to ooze out. At that point, I gave in to temptation and wrapped my lips around it, tasting the precum and sliding it in and out of my mouth, getting it more wet than it was. It was for a time like that this that I had my lip rings, which caressed the shaft of his cock from his head down to his balls, which were completely shaven.

While I sucked his cock, my hands ran up and down his legs, which were silky smooth, and looked just as good as any girl's legs that I had ever seen. As I wrapped my arms around his legs, I could feel his cock start to get slightly bigger, then I felt his warm cum rush into my mouth He sighed softly as he finished cumming, and I stood up slowly, and kissed him with his cum still in my mouth.

He just stood there, amazed, as I withdrew my tongue from his mouth. He may have been speechless, but I wasn't. "Turn around hun," I told him. He stood there, baffled, and I slowly turned him around where he stood. I reached for my purse and pulled out a bottle of lubricant. "Bend over, sweetie," I ordered him. He laid his face flat on his car's hood, as I pulled his skirt up in the back, and allowed myself to drool a little bit on the crack of his butt. Oh it looked so adorable, seeing him bent over like that, with his skirt up and his cock hanging between his legs, and that perfect butt that was about to get invaded.

I put a small drop of the lube, which I had put a bit of flavoring in, on his butthole and slowly worked it around with my finger. I cautiously slid my tongue down his crack, then licked his butt until it got relaxed enough for me to slide my tongue into him. I slid it in, tasting the vanilla flavoring I had added to my lube, making his butt taste delicious. As I slid my tongue farther in, I silently pulled up my dress, revealing my dirty, not-so-little secret. I gave his butt one last kiss, then I stood up, gave my cock some lube, and slowly slid it into his butt. I heard him whimper like a girl as I slid it farther in, until I couldn't put it in any farther. I pulled back out until only the head was in him, then began to rhythmically push it in and pull it out. I could tell that he was hurting slightly, so I tried to be gentle with him. It didn't take me very long before I burst inside him and he let out a high-pitched sigh of relief. As I slowed down and eventually pulled out, my cum began dripping from his butt. I squatted back down and licked it from him, then stood back up, turning him around, and kissing him again. 

As I forced my tongue into his mouth, I could easily tell that his reluctance to taste my cum was easily overcome as his arms became wrapped around my back and we continued to play with each other's tongue until we eventually grew tired. The kiss finally ended, and I held his hands in mine loosely. "Did you enjoy yourself?" I inquired eagerly.

"Yes I did," he replied, still trembling with nervousness. "But... where did that guy come from, and who was he?"

"Oh, there was no guy."

"Then, who WAS it? Or what was it?"

Pulling my dress up, I responded, "It was me, baby." His eyes bugged out as he saw my cock. I could tell that he wanted to run, but he was frozen in his tracks.

"Oh my gosh. I just took it up the butt from a GIRL!"

"Why yes darlin', you sure did," I giggled, almost happy to see him in mental misery. "And you enjoyed it so much, it was worth it just to hear your cute little girly voice and to see your adorable figure. I just couldn't resist myself. I'm sorry if I hurt your butt when I went in."

Not knowing what to say off-hand, he couldn't help but glance at my crotch. "I don't know what to say. This is almost like a dream come true, but in a demented way," he replied, still somewhat lost for words. "I always wanted to see how it felt to be a girl having sex, and I came up here dressed as a girl hoping to find a guy that would do me, and not mind the fact that I was also a guy, dressed as a girl."

Trying to reassure him, I said "I kinda figured that's what you were up to. I was kinda torn between trying to help you find a nice guy to have sex with and what I did. You were just so adorable I couldn't resist myself and I knew that I wanted to have you for myself, and maybe even date you eventually. After all, if you can express your feminine side that well through dress, I think you'd be a decent boyfriend, or maybe a decent girlfriend."

Still in a state of shock, he finally asked me one thing that I was surprised he didn't ask before. "Just how did you know I wasn't really a girl anyway, if I was so convincing?"

"Honey, you made a huge mistake tonight. When you went to the bathroom, you went to the men's room. No girl, no matter how drunk she is, would do that. You, on the other hand, did."

I could tell that I burst his bubble. I didn't really know how to make it up to him, since I wasn't sure whether or not he really wanted me to have done what I did to him. Being the sentimental ball of mush that I can turn into on occasion, I almost began to cry. I grabbed his hands, not wanting him to go anywhere, and decided to try my best to keep this cutie around. "I know I may not have been the most polite girl in the world. I hugged you, kissed you, sucked your cock, then did you with a cock that you didn't even know I had, and we don't even know each other's names. I feel horrible about myself, but, but, I want you for a boyfriend. I don't know much of any other way to put it, but I've tried for years to find someone like you, and I don't want you to just slip away."

The second or two of silence seemed like an eternity. Despite the fact that he hadn't moved an inch, it felt like he was running away from me at a mile a minute until he finally replied, "I know where you're comin' from. I've tried to find a girlfriend for years, and all I've found have been folks who just want a boy toy and don't care anything about a relationship. Then, when they find that I prefer a skirt and heels over sneakers and jeans, they freak out. I had one girl kick me out of her house on spring break and left me on the beach naked. I sat there and cried for almost an hour before some drunk girls came along and one of them gave me her sarong so that I could salvage a small amount of my dignity when I went back to my hotel. That's the kinda stuff I'm used to."

I could tell that he was about to cry. I didn't say a word. Instead, I just reached my arms out and we embraced for quite some time as he cried into my shoulder. Though it pained me to see him cry, I felt a great sense of relief in the fact that I had gained a friend, one who not only understood my plight, but also accepted me for who, and what, I was, despite his confusion about me. 

It was hard to say goodbye to him, and we finally parted company after an exchange of contact information. The drive back to campus seemed to take forever, even though it was only forty or so odd miles. It was about 4AM as I walked back to my dorm, somewhat tired, somewhat jittery, and somewhat satisfied with myself. As I walked down the hall, I stopped at the door of my neighbor who had taunted me on the way out. Opening up my purse, I pulled out a souvenir that I had acquired in the parking lot. On her doorknob was draped a pair of silken panties, that had a small amount of precum in them.

A Trip to the Park



March can be a strange time of year for weather in the UK. Only a month ago there was six inches of snow with road closures and snow days, now we were having a mini summer with bright sunshine and temperatures normally only reached in July or August. It made the ten minute walk to the park very pleasant and despite the warm temperature there was still a cooling breeze just to remind you it was still technically the tail end of winter.

I walked quickly partly out of eagerness partly out of habit. I forced myself to slow down slightly just to make sure that the combination of heat, excitement and fast walking didn't cause me to sweat. I didn't want the first time we were alone together to be marred by me being a sweaty mass.

I had taken the opportunity earlier to get prepared, fresh deodorant and after shave and cleaned my teeth again so there wouldn't be any coffee breath, in doing so my mind raced at your own preparations wondering if you would follow all of my instructions and how far this game would go.

Your works conference was the catalyst, the flirting and mild innuendos we previously shared suddenly blooming and growing as we shared our experiences and limits of our own sexual pasts. It took me by surprise when we compared our experience, things we had done, things we hadn't. Things we wanted to do and things we wouldn't. Your list of ticks was far greater than mine and the tales we shared of previous experiences driving us both to distraction many times over the last month or two.

One thing that did come out of our chats was your desire to be tied up, just the thought of being restrained and utterly at someone else's mercy got you all hot and wet.

As our relationship was purely electronic, texts and e-mails, we shared many fantasies over the weeks. Generally I took the lead, setting the scene and steering the action of our story - because that's all they were stories of two (mostly) people getting together for a sexual encounter, the characters weren't you and me. They were just a random boy and girl that we controlled their actions. It was quickly obvious you were using the stories to get yourself off, not that I minded at all, after all that was the whole point of the stories and so gradually we moved from describing a third party sexual act to me telling you what to do, where to touch yourself and finally giving you permission to cum.

Normally I wouldn't even consider you as submissive in the slightest but without any physical interaction between us, you adapted to a lack of ropes and ties by following my instructions and letting me tease and pleasure you at my convenience. Often taking you to the brink of an orgasm and then making you stop only to build you slowly back up and do it again.

The control was all about trust, you could easily have ignored me when you were close and continued against my instructions but the thrill you got and the occasional self administered punishment made the orgasm so much more intense when it finally came. As each day went by we built up a trust and bond, I became the conductor for your solo performances, taking you to orgasm time and time again for your pleasure and also for mine.

At the start, just after compiling our sexual do's and don'ts we wrote up a brief set off rules for our activity together.

1.We don't meet.

2.No emotional connections were allowed.

3.We both describe in detail any sexual activity conducted since we last spoke.

4.You follow all instructions given.

Fairly simple but we both agreed and from that point you gave control of the relationship to me.

All of this was going through my head as I stepped into the car park and spotted you sitting behind the wheel of your car. Rule number one about to be broken and I could feel my heart thumping under my shirt.

You hadn't spotted me so I stopped and admired you for a minute, you adjusted your hair and sat quietly checking your phone to see if there had been a message in the last three seconds since you last looked. Dragging your eyes away from your phone you notice me standing on the other side of the car park and you are filled with both relief and excitement that we are meeting at last.

Despite the rules we both made you had been increasingly keen to meet up, I guess touching yourself under instruction isn't quite as good as being touched by someone else. I slipped into the passenger seat and closed the door. We smiled and said hello before leaning together to kiss deeply.

The kiss was electric, sparks of passion jumping between us and despite the fact it was short, it confirmed the lust that we were both feeling at that moment.

I pulled away and put my seat belt on as you started the car, eager to head off for a little more privacy than the car park currently offered.

You looked fantastic and seemed to have followed my instructions regarding your clothing, a knee length skirt with a cream blouse over the top. Your hair loose and straight and very light make-up, less to get smudged if things got heated.

Before we are even moving light spots of rain splash against the windscreen and quickly becomes a light shower as you drive carefully away.

You started some small talk as you drove away from the car park, the destination already selected but you weren't in a hurry as my hand slipped underneath your skirt. My fingers stroked the inside of your thighs brushing against your knickers then on to the other thigh. I teased a few times up and down your thigh briefly touching your pussy through your knickers before moving away again. On the third pass you spread your knees wider, concentrating on your driving but urging my touch to linger where you wanted it. I didn't disappoint you. Finger and thumb softly rubbing you over your knickers as you stared straight ahead at the road and drove, conversation now stopped as we both concentrated on different things. Your wetness was already showing, a small damp spot on thin material as I push it firmly against you pussy. My finger pushing your knickers lightly between your lips as I run it up and down between your legs.

Hooking the material to one side I moved my fingers in to direct contact with your skin, your pussy open to my touch and welcoming a finger to slip inside to a small sigh of pleasure from your mouth. I teased you slowly as you drove, a single fingertip just inside you playing between your lips then running up and down your slit to brush your clit before returning to your hot wet hole, marginally deeper than the previous visit, repeated over and over again.

By the time you pulled in to the deserted park my finger was fully inside you, my thumb caressing your clit up and down as you parked away from the entrance overlooking a small boating lake.

Pulling the handbrake on and switching off the engine you pushed your knees further apart, now free from the constraints of operating the pedals with your feet as I insert a second finger inside your pussy. I don't want you to cum yet but enjoy the soft noises you make as I played with your clit, finally pulling my hand away leaving you short of your climax.

I made a show of sucking one of my fingers clean of your juice then offered the other finger to you to have it immediately sucked into your mouth, tongue flashing around my digit tasting your own womanly scent on my hand.

Fingers cleaned we leaned together for a kiss this time hands roaming over each other, your hand goes into my hair, mine immediately onto your breast. My first feel of your fabulous 34GG tits pressing into the palm of my hand albeit through your blouse and bra. Even through the double layer of material I can feel your hard nipples prominent on your full breasts.

Easily unfastening the top two buttons on your blouse I slip my hand inside and cup your breast again, thumb rubbing your nub circling it slowly as my tongue swirls inside your mouth.

A car drives through the car park dragging your attention away from me briefly, your eyes on the mirror watching it drive past. Fortunately the rain now heavy enough to put off a visit to the small park.

"Take your knickers off" I tell you when your attention leaves the departing car. You comply immediately, raising yourself slightly in your seat to ease them down your thighs, then down and completely off. Balling them up and pushing them into the driver's side pocket of the door.

My hand moves your skirt up exposing your pussy to my view as you sit and wait as I admire your trim little bush. I eased your legs apart with no resistance spreading your tight little pussy wide open to my view. "Play with yourself." I demanded and watched you quickly drop a hand onto your pussy. Two fingers pushed deep inside yourself thrusting in and out wetting your fingers and causing a small squelching noise with each thrust. Soon you removed them and rubbed your pussy hard from side to side your pink pussy glistening with your juice. Finally moving up to your clit and very quickly flicking over the same spot as your eyes closed and you rested your head back against the car seat.

Moving to my knees I bent forward and pushed my face between your spread thighs getting my mouth onto your pussy and my tongue working up and down your cunt just as you cum with a small moan of pleasure. I continue lapping at your pussy savouring your taste until you physically pull my head up towards yours kissing and sucking your own cum from my lips like the hungry little minx that you are.

My erection is now quite uncomfortable within my trousers the touch and taste of your pussy making me harder with every passing second. Sitting back on my seat I unzip and pull my straining cock and balls from my underwear which proudly points to the roof of the car. You don't hesitate but immediately lean over and sink your mouth over my exposed cock, pushing the whole eight inches into your mouth before your nose brushes against my pubic hair. I have trimmed it especially and shaved my balls too, but your mouth slurps noisily on my cock as you quickly move it up and down my shaft eager to please me after your own orgasm.

"Slow down" I tell you, holding your head in place and resisting the urge to thrust my hips up a fuck your face hard. That will be another time I tell myself and release my grip allowing you to suck and lick my cock more slowly.

You move your hand to join in and gently cup my balls, softly massaging them and pulling on the skin as you lick and suck on the end of my cock. From your position bent over me I slip a hand under you top and push your bra over your breasts so they hang, dangling from your body. My fingers quickly find your hard nipples and begin pulling and twisting on the engorged buds as your head begins to bob up and down on my cock again, gradually building up the pace as I maul and squeeze your breasts. I'm conscious of my breathing now and the sensations tingling deep in my balls, ideally I would stop you now and drag you out of the car to fuck you over the bonnet but the rain has stopped and another car has parked in the car park, far enough away from us to not disturb us but the mere presence curtailing the chance of an outdoor fuck today.

The thought lasted only a few seconds anyway as you roll your tongue around my head and squeeze my balls triggering my cock to twitch and spurt cum into your mouth. I feel three or four big spurts ejaculate into you followed by a number of smaller twitches as the last of my seed seeps from my cock, all of it greedily sucked up and swallowed as you pump my cock with your hand trying to make sure you get every last drop of cum from my cock into your mouth.

Satisfied I have nothing left you kiss my softening cock and having swallowed my load, lock your lips onto my mouth and let your tongue dance inside my mouth like it had done around my cock seconds before.

Only know do you notice the other car and self consciously adjust your top to cover you boobs which I had completely out and was still tugging on your nipple. You don't remove my hand but just push your top over it to avoid a stranger getting an unexpected eyeful if they looked in our direction.

With both of us having cum we adjust our clothes back to respectability and with another car pulling into the car park we decide it is time to make a move. My fingers slipping under your skirt one final time to tease your pussy as I tell you what a close call you had, saved only by the car, that you didn't have your pussy fucked over the bonnet today.

I can feel by the heat and fresh wave of wetness that the idea excites you and will mean we plan another adventure sometime soon, as you drive us back to our original meeting place and the end of our lunch time liaison.