A Trilogy of Trannie Tales

Terri and I had been having phone sex with each other on a telephone chat system for several days. We agreed to meet and go to my favorite park one day at around sundown, when most others would be leaving the park. Our intent was to flirt with and fondle each other around the other people, and then fuck in the park, after everyone else had left.

Terri was an attractive woman, with sort of a dusky brown complexion, smooth skin, tall, and with a shapely figure. She had nice hair, black, and down to her shoulders. high cheek bones (facial and butt), and she was very confident about herself. She wore a nice flowered print and black skirt, very short, but not too tight, because we wanted for me to be able to suck her pussy once we thought we were alone in the park. She was wearing a loose fitting blouse, with the top buttons undone, so I could play with her titties. Did I mention her big, hard nipples, just the kind that a man loves to suck on and pull on within his mouth...

Terri was to be my sex toy, and she was dressed for the part. If she bent over, anyone could see her pubic hairs jutting out from her pussy or ass cheeks. But, she didn't—she knew she was there for my pleasure, and she knew I enjoy watching erotically dressed, sexually endowed women. Her large, bosomy breasts heaved against her filmy, tight blouse, and she had no bra on. I could see her big nipples, taut and pointy, as they pushed out against the blouse. She had on thigh-high stockings, black and very sheer. She was made up for fucking, and she wanted to be made to be nasty.

She walked a bit in front of me and off to my left side, her ass cheeks seductively undulating under the short skirt. She knew I was watching every step she took, and that I could hear the sounds her stockings made as they rubbed against each other.

Moving closer to her, after looking to make sure no one was watching, I grabbed one ass cheek through her skirt, feeling it move up and down. I gave it an extra firm squeeze, and pulled it away from the other cheek, simultaneously pushing the edge of my palm into the crevice, hard against her asshole. She reacted by bending slightly forward at the waist and pushing her butt back hard against my hand.

I grabbed her ass cheeks with both hands, and pulled them wide apart, stepping up against her ass to push my dick muscle hard against her skirt. She moaned and pushed her butt against me, trying to get my cock up into her asshole. Knowing we could be seen by anyone who came into view on the trail only increased the thrill.

We reluctantly strolled on, with her strutting, and showing her ample ass(ets), just a tiny bit short of being lewd and indecent. A bit further on, she turned, looking to be sure I was watching her graphic display of exhibitionism. I licked my tongue against my lips and pulled my hard cock from under my shorts and shook it at her. She licked her lips in response, anticipating a chance to swallow some warm wet cock juice.

I motioned for her to take a path that went down to the edge of the lake, under a Pussy Willow tree. I followed her, grabbing her ass cheeks again as our nervous sexual energies made us look furtively to ensure we were sufficiently isolated from others in the park.

She was erotic and hot, strutting her stuff in three-inch pumps and thigh-high stockings. Her blouse was already half open, and I could see her tits, jutting out, almost visible. She was already turned on, playing with herself, and teasing me.

We went to the edge of the lake, under the tree, supposedly to look into the water. When I was sure no one could see us, I let Terri stroke my cock, and I fucked it at her, asking her to suck it. She squatted, opening her long legs (I could see her red bikini panties) in the process. I could smell her sex. She reached under my shorts, pulled my throbbing muscle out, and began to tongue my piss-hole! Then she reached behind me, grabbed my ass cheeks, and began to fuck me in and out of her mouth. She gagged on my hard, black dick, as if trying to get the entire shaft down her throat. I fucked her mouth hard, like it was her pussy! I wasn't about to let her take my load there, though... I had other plans. Little did know that Terri had her own special plans for me!

I pulled away, telling her that we had plenty of time, and other places in the park to visit. She agreed, and got to her feet, as I playfully squeezed her ass, spanking it in the process.

When we got to the deepest part of the park, it was virtually dark, with the moon providing enough light for us to play. We looked around, and saw that we were the only people left in the area. Terri opened up her blouse, and exposed her tits to me. I squeezed them for a time, then sucked on them hungrily, licking and pulling them with my mouth. She said it was something she always fantasized about, sucking dick, and having her titties suckled, right out in public. I told her it was just an appetizer for what was about to be eaten. She laughed.

She ran to a park bench, and sat down on the back of the bench, with her feet on the seat. It was time to eat some hot, wet pussy, right out in the open. I sat on the bench, close by her legs, and began to feel her up on the insides of her thighs. She pushed my hand away, and closed her legs. Of course, I was not about to be denied, and rubbed her legs, until she opened them again.

Terri said, "watch out, or you're gonna get something you'll remember for a long time!"

I wondered what she meant by that, but only for a second. There was pussy to be eaten, and I could feel the heat coming from between her thighs.

I began to kiss her stockinged legs, and she shuddered, seemingly wanting me to kiss up further. So I did. I licked little trails of saliva above her knees, on the insides of her thighs. She started to moan, now in heat, and needing something hot, hard, and wet. Was I gonna make her wait? Hell no!! I reached up between her legs to pull her panties off, and she again closed her legs, clamping my hand tightly, just short of her sex.

I looked at her in the moonlit night. She was beautiful, and I could see a mixture of desire, and uncertainty in her face. She wanted me... I knew that. But there was something about her that I was missing. I asked what was wrong. She asked if I was sure I wanted to do this. I was not about to stop now, so I said, "sure!"

She took another look deep into my face, and said, "okaay!"

I began to lick her legs and thighs again, and she pushed herself out at me, an invitation for me to stroke her. I put my hand back under the skirt, and felt for her panties. As I felt them, and began to tug on them, she thrust against my hand, and I felt a warm, hard bulge, where it should have been soft, hairy, and fleshy. I pulled away, startled and unsure what was going on. I looked at Terri—she opened her legs, pulled her skirt up a bit, and I could see the unmistakable outline of a hard, throbbing cock.

I immediately jumped up, and moved away, standing about fifteen feet from Terri. She was still a very attractive woman, but I had just had a very severe jolt to my psyche!

After about a minute (it seemed like ten) Terri got up, walked over to me in that still very feminine demeanor, and took my hands in hers. I looked at her. She was still smelling good, smelling sexy and erotic, and I was still horny. She must have known it, because she took my hand, and placed it on her hardness, making me feel the bulge under her skirt. It was very big, still jumping, and hot. Terri humped my hand with her cock, and kissed my neck, at the same time feeling my cock growing massive and hot at her touch.

She worked my dick, and I started working her cock for several moments, until we were going at each other, feverish in heat to fuck. I didn't know what to do—I'd never so much as looked at a man's cock before, except in fuck movies.

Terri did, though. She went back to the bench, taking me with her, and sat again on the back of the bench, her feet on the seat. This time, though, she had me sit between her legs, which were wide open, her skirt high up on her meaty thighs. I looked at her bulge with amazement. I'd never imagined myself in this situation. What would I do? How would I ever take a cock in my mouth?

Terri took my head, and guided me slowly against her left thigh, rubbing herself against my face. She started to hump slowly, letting me feel the heat and passion. She took her huge cock from under the panties, which were wet with pre-cum (not pussy juices!).

She rubbed her cock against the side of my face. It smelled like sex, and was erotic and inviting. Resisted—I'd never tasted cock. This was the most powerful, erotic, perverted, and nasty sexual urge that had ever tempted me. but it was sex, and that was what I needed.

Tentatively, I let her put her cock to my lips. I didn't open my mouth at first. But then, the intensity of the moment got to me, and I parted my lips, slowly, unsure of what it would taste like. I kissed Terri's cock.

Curious, I stroked her, then started to pump it, up and down. I stroked it, short strokes, hesitantly at first, then longer and more forcefully, until I was masturbating Terri, wickedly with my fist, pumping her huge black dick furiously, watching the uncut dick head opening, and then disappearing into the foreskin.

I stroked her dick grotesquely, yanking it up and down, left and right, sniffing it, loving the way it smelled.

My eyes were glazed with desire. I knew I was gonna suck it, eat it, lick it, and chew on it; so I pulled it into my mouth, nipping the bulging head with my lips, and tonguing her piss-hole in the process.

Terri pulled away from my hungry mouth; she wanted to show off, before I sucked her off. She stood on the bench, her cock hanging straight out from under the hem of her mini-skirt, rippling and glistening in the moon light. She looked at her huge cock, as if hypnotized herself by the erotic pulsing and pre-cum dripping from the head. She stroked it, opening and spreading her legs to stretch the skirt taut about her thighs, dancing raunchily, looking at me with lust filled eyes. She pulled on the shaft, beating her meat, jacking it off, and sliding her fingers over the lubrication pouring from the cock.

I went to Terri, my body trembling, my mind out of control with lust. She put her dick-meat back into her panties, and pulled her skirt down. I put my head against the skirt, and I could feel the steel hardness of it, as it pulsed, and strained to burst free from where she had hidden it.

I could smell it, and feel it—I succumbed to the very nastiness of knowing that a nine-inch cock was held in place just on the other side of the short skirt. I was also somewhat surprised to realize that I was trying to get even closer to it than I already was. I swiped my tongue at the outline of the cock, and then mouthed along the shaft, blowing heat against the material. Terri was surprised, and gasped at the warmth of my mouth. As I blew heat onto her meat through the skirt, Terri began to cumm!. I moved away, surprised that she would cum so easily! She spurted jets of cock-cum against her skirt, soaking it through to the outside.

I couldn't hold out anymore. I needed to experience my first cock-sucking. I licked into her as she stood, sucking lightly on the inside of her smooth warm thighs. I licked upward, to the bottom of her skirt, out of my head with desire. Terri put her hands on my head, and pulled my face onto her wildly swinging black meat.

Soon, I was sucking Terri wickedly, tasting her cum, just the way I would want a woman (Terri?) to suck me. And she fucked my mouth just the same way I had fucked her mouth under the Willow tree! I gagged on her massive cock! I had saliva and pre-cum running out the sides of my mouth and down my chin. It felt so perverted!

After about twenty minutes (I didn't want to stop sucking), Terri pulled away, and announced that she wanted to be fucked. I wondered about that too, but she moved to a treed area, and pulled her skirt up over her ass. My cock was instantly rock-hard—I've always enjoyed fucking assholes!

I moved behind Terri, and she parted her ass cheeks, exposing her tight hole for me to work. She lubed herself (think she had some K-Y), and stuck her ass back at my cock. It went in readily, and I began to stroke her ass, while she pushed back from the trunk of the tree to get my cock in further.

I ass-hole fucked her, slapping my nuts against her own nuts, and listening to the sound her ass cheeks made as she banged back against me. We fucked that way for another fifteen minutes. Finally, I grabbed her cock! It was still rock hard, and I began to masturbate it while I fucked her up her ass! Terri began to cumm! She began to spurt thick cum against the base of the tree. I got so hot watching her shoot her cock-cum that my own juices shot straight up her ass! I didn't pull back; it wasn't like she'd get pregnant.

Terri enjoyed feeling my cum shooting into her. She pushed back hard, grinding her ass at my cock. She was in a very erotic state.

Finally, we left the park, and went back to my place, where I fucked her like a proper woman needs to be fucked, in the ass.

***

Author's note: This segment is taken from another of my stories, 'Danielle's Day of Debauchery,' for the express purpose of exposure to/entertainment of those who enjoy reading Literotica Transgender stories.

Danielle couldn't believe it--all the hardcore sex she had been involved in since the beginning of the day. She needed to share her good fortune with Terri, her neighbor. Of course she didn't intend to tell Terri about the episodes with Randy and Judy; but Jerry, Danielle couldn't wait.

To let Terri see the outfit which had finally seduced Jerry, Danielle put on in the dress which she had bought that day, along with the stockings and heels she had worn to work, and went next door to Terri's home. As usual, she took the shortest route and entered through Terri's back door. In the kitchen, Danielle was about to call out to Terri, when a sixth sense told her to be cautious.

Instead, Danielle walked down the hall and was about to enter Terri's bedroom, where Terri spent a lot of time, when she noticed Terri in the bedroom, admiring herself in the floor to ceiling mirrors that ran the length of the wall. Danielle watched silently.

Terri had on extremely high spiked black heels, with welted white seamed stockings cinched tightly to her garterbelt. Her skintight miniskirt had a slit right between her legs. She was naked from the waist up. Danielle could see Terri`s small but firm breasts, with the nipples pulsing, jutting straight out.

Terri was massaging her titties, looking at them in the mirror, moving suggestively back and forth. Her eyes were glazed and she would occasionally jut her ass out erotically. Terri bent over and grabbed her ankles, looking between her legs to the mirror, so that she could see the dark swatch of hairs nestled high up in her ass crack. Danielle watched quietly, eager to see what Terri would do next.

Terri was turning herself on. Danielle, still watching intently, could feel herself getting wet also. This was a peep show worth watching from a front row seat!

Terri squatted lewdly, moaning as she saw herself in the mirror. She gapped her thick thighs apart wildly, and grabbed at her ass cheeks with her free hand. Danielle, suddenly in need again, was about to go to Terri, when something happened that she wouldn't have ever imagined about Terri.

Danielle watched Terri move one hand down under the hem of her mini, to feel underneath it. She reached up and pulled out a huge, turgid cock, which was now hanging well out of it's protective glans and dribbling pre-cum. Terri masturbated wickedly, feeling the cock grow even more massive. She slid to the lounge grotesquely, trying to fuck into it as if it were human!!

Terri was out of her mind with need, her legs splayed wildly apart and high into the air, jutting off each side of the lounge. Her miniskirt slit was right at the level of her hard meat, her hair was disheveled. Terri was in heat, in glorious dog-style heat, and she didn't know where to go to get the fires going even hotter.

Terri began sobbing in rapture, "O-oh, fuck me—do it to me, baby! Ag-ghh! I need to cummm so-o baadd!"

Danielle came silently, dropping puddles of pussy juice in Terri's hallway. "U-ngg!" Terri came, her asscheeks lifting off the lounge.

Terri, her cock still leaking cum, finally saw Danielle with her fingers working nastily in her pussy, staring at her! When Danielle looked back at Terri, she was still on the floor, her miniskirt riding high on her thighs. Between her legs was one of the biggest cocks Danielle had ever seen!!

Terri was shocked and distraught at being discovered, "I-I didn't mean for you to see me like this—I n-never wanted you to know!"

"But, but you-you've got a cock!" Danielle replied, still in disbelief.

"Yes, I do..." Terri said, calming down a bit. "You've become my best friend in the whole world, and I'm very attached to you. I often wondered how you would react if you knew the truth about your next-door neighbor."

"But, you... you seem so much like a woman!" Danielle asked, bewilderment in her eyes.

"Yea-ah—so... let me tell you the whole truth about me," Terri responded, trying to make the best of being found out.

"Please do... I need to know everything!" Danielle asked, trying to keep some sense of openness about her friend's obvious hidden sexual identity. What Danielle had experienced so far during her own day was nothing, compared to this discovery.

***

Terri began.

"When I was a teenaged boy, in high school, I began trying on my sister's clothes, when no one else was home. I'm not homo—I couldn't be with another man. I just like the feel of sheer stockings, garter belts, and other feminine clothing against my skin. I'm not particularly big boned for a guy, even though by a woman's standards, I'm a pretty good sized woman."

"I never wanted to be a total woman then—just to dress in women's clothes."

She went on.

"In college, there was this teacher I was very attracted to, but she wouldn't give me the time of day. She was very attractive and wore tight fitting skirts that outlined her sexuality explicitly. The word was that she was having sex with some of the female students, and I thought I'd try to approach her as a woman—just to see how well I could pass myself off as one."

"It worked," Terri continued.

"I found out she frequented a lesbian club. I began hanging out there myself--as a young woman, long wig and all. One night she came in, by herself, and she approached me, after we'd both had a couple of drinks. I introduced myself as Terri, and she never made the connection between me and Terry--the male student in her class. She asked me if I wanted to slow dance—I said I was not into public displays of affection. Actually, it was because my cock was throbbing so hard, I was afraid I'd shoot my wad—and my secret, right there in the bar!!"

"So, we went back to her place. I was having second thoughts—what would she do when she found out I'd deceived her. We sat close together—like you and I are sitting now, and kissed deeply. My skin was so smooth, that she never guessed I'd shaved a couple of hours before."

"Wow!!" Danielle said, getting turned on again. She glanced down at the bulge under Terri's skirt, putting herself in the teacher's place.

"She opened my blouse, and found no tits. Her eyes looked at me questioningly. The moment of truth—I pulled up my skirt, and let my massive cock fall free. Her eyes went even larger. She was shocked speechless. I decided to make the most of it. I grabbed her and pulled her up from the sofa."

"I pulled her close to me and kissed her hard on the lips, then my mouth roamed down to her smallish titties, and I began to suck on them. I remember, there was a sensual record playing, softly on the stereo. I began to dance with her slowly, in one spot on the floor, grinding my manhood in between her legs. She moaned, temporarily distracted that I had deceived her. I was gaining her favor. I took her hand and put it behind my back, low to my ass cheeks. She resisted. I pulled away and looked at her. I was still a very attractive woman to her—even though I had a bulge, where my pussy should have been."