I looked at my stomach in the mirror. I couldn’t believe it. I felt like I was gaining a bit of weight.
"Fuck!" I said to myself out loud. "My tummy feels bloated! I need to get in shape again. I'll wake up early to go running."
Normally, I would wake up before 5:00 am to do some stretching before running. I usually dressed in men's workout attire on weekdays. On weekends, however, I'd change it up and exercised in my female attire, dressed as Sasha, my feminine alter ego. It had been that way for about a year now.
Currently, I live in a quiet neighborhood about five miles from my junior college. I moved out of my parents' home for my own sanity's sake. I have a job, a girlfriend (who is completely unaware of my crossdressing, and would like to keep it that way), and also loads of free time to be the girl I that I am inside in the privacy of my own home.
I live in a small in-law studio adjacent to the main house. The family I'm renting the unit from are very cool with my personal life. They pretty much don't care what I do or who I bring over, as long as I keep it quiet and pay the rent on time. Fair enough, right?
The back door of my studio unit leads me to the running trail. That's where I always start my morning jogging routine. I'll admit, the trail is a very lovely place. You could run as far as you like to enjoy the scenery, the tree tunnel, and if the mood strikes you, you can go to a certain area about a mile away from the trail path, where some go to have a little “fun”. I attest to this because I have gone there a few times with my girlfriend when she stayed over. When she didn't, I would go and have a few encounters with other people, if there were any available.
Three weeks ago, I had an encounter with beautiful, older woman. She was curvy, petite, and in her early sixties. I swear she looked not a day over forty. She had ginger red hair and almost no wrinkles on her face. She wore a black tight sweatshirt and leggings. While we were passionately making out, she stripped down to just her purple thong.
I bent her over, moved her thong to the side, and pushed myself into her pussy. All throughout our morning of sex, she acted like a woman of twenty-five; the way she pushed her soft and spongy butt back and forth at me with such force and passion. It was more than I could take. She cried out for me to come inside her. We remained in a doggy-style position until I filled her up nice and good.
I also had chance encounters with a couple of guys when I went out as Sasha though they were individual spontaneous encounters. I will admit that I had considered having a threesome if that moment came around.
I always fantasized myself being in a threesome like this: I was on all fours, wearing only my bra and thong panties with my ass up and one guy behind me as he is sticking his thick cock through a slit I cut open on the back of my thong. I have another guy lying in front of me, legs spread, completely shaved with his dick in my mouth while I suck on it good and slow.
While he watches me get pounded by my other lover, he begs me to let him fuck my ass after the first guy dumps his hot load inside me. After the first guy unloads himself in me, the second guy comes and shoves his hot dick and fucks me harder until he comes inside me.
Damn, I want a guy in my ass so badly, I thought to myself. That fantasy made me hot and horny, I couldn't help myself but jerk off until I shot my own load all over me.
Seconds later, it hit me. I thought to myself, Why wait to run tomorrow morning when you can do it now?
Sure. It's a great idea, but it was nearing midnight. Who knows what kind of people are out there this late at night. Not to mention it was a late Friday night, and it was really foggy. Some psycho could be prowling for anyone. I could get into a lot of trouble, yet it actually made me want to go out and do it more. Yes, I was still horny, and, yes, I also needed to get some exercise. While I thought these things, I noticed a few running out late, too. So, I figured it was safe. I hadn't heard of any recent incidents that involved defenseless people running in this trail. The only real risk I took was getting caught by a ranger or police for violating a park curfew.
"To hell with it!" I said. “Let’s do this. Sasha is in the mood for fitness and some fun!" But, before anything, I went off to take a shower to clean off all my cum after I let myself go crazy in my own daydream.
After my shower, I got dried up and pulled out my running clothes. Since it was foggy, I needed to wear something bright so that I could be seen in case someone bumped into me while they were running. I put on a special white workout thong with a gaff that pushed my nether regions in. I cut a slit on the back of the thong before I put it on.
I also wore a black workout bra with my silicone breasts to give myself a slightly busty look. Then came my white fleece pullover, white flared bell-bottom yoga pants, and my socks and trainers. Of course, I didn't forget to put on a bit of foundation and lipstick, and a small black wig. I was ready to go!
I decided to take a spare thong in case of an emergency, and I put it in my fleece top pocket.
So, there I was, about half a mile already in, and it was ten past midnight. I was out jogging in this cold, wet, and foggy Friday night, and I was thinking how the hell was I gonna get lucky this late at night? There was nobody around, and I began to feel stupid and scared. And pretty soon, I would get into trouble. What would happen to me? And what would my family and girlfriend think when they heard that something happened to me in this trail?
Or worse, what if I had been caught dead dressed as a girl? Well, firstly, they would say: “Why did you go running this late at night?” Secondly: “Why in the fuck did you dress as a girl?" Oh, boy! If that happened, and I survived whatever accident it was, I know I wouldn't hear the end of it from my parents. In my girlfriend's case, it would be the end!
Dammit, Sasha!, I said to myself. You could get into a lot of trouble now. Let’s turn around and go back. That was enough for one night.
Yeah, fun indeed.
Before I could turn around, I heard what sounded like footsteps. And they were getting louder, and faster. Oh, shit! I wasn't going to turn back. In my mind, I thought that this was it. If something were to happen, better I wound up dead after it. My heart was ready to jump out of my throat as the sound of running got louder. And then, slap!
"Wake up, girl!" a middle-aged black man yelled as he slapped my ass. It hurt!
"Ouch! You dumbass!" I yelled.
Suddenly, he stopped. I thought: Oh, shit! He’s gonna kick my ass now!
He walked back and stopped in front of me and said: "Look, bitch! You was in my way. Now, I could’ve just ran into your hot ass and hurt you, or just move to the side and give you a heads-up that I was running and smack your hot ass. Either way, I was gonna hit ya!"
We glared at each other for what seemed like an eternity, only for him to kill the mood and yell: "WHAT?”
What? What, what?, I thought. I couldn't say anything. I was still in a terrified state. I just looked down. "Sorry, man," I said in my raspy, timid feminized voice. "You just caught me off-guard."
"Hey, it's cool. Shit like this happens all the time. Just gotta watch yourself, baby. What if it was some wacko who wanted to rape you, only to find out you are a dude in girl’s clothing? Then, you better pray hard that he don't kill you!"
Eh? How did he... how did he know?
"You’re shocked because I said that, huh? Because I knew you’re a crossdresser?”
I mumbled out a, "Yeah, little."
"Don't worry. As far as I'm concerned, they are women, too. Only, they still have a dick. It’s nothing to worry about," he assured me.
I chuckled. "Thanks."
"So, what's a cutie like yourself doing at this hour?"
Stupidly, I responded, "Would you believe, to exercise?"
"Damn, girl. You don't have to be so rude. It was just a simple question."
I felt bad.
"Sorry, man. I'm just a bit nerve-wracked from your hard slap on my ass. But, yeah, I just needed a bit of fresh air. Trying to get back in the groove of things."
"I heard that. You and me, both. My wife is trying to push me to get some exercise, too. Can you believe that?"
"Hey, she loves you. That's important," I replied, giggling with him.
"Good thing my wife is pulling a half graveyard tonight, so I wanted to prove to her I got some running done today. She checks my pedometer every day."
"Really?" I asked. "Why?"
He said, "She's a nurse. Plus, she checks my glucose levels every night just to make sure they're normal."
Wow, I guess he was diabetic. That was the only thing that came to my mind. I didn't want to ask him, though. Then, he got closer and put his hand on my ass, which sent my blood rushing from his touch.
"Sorry, I hit you so hard," he said as he began to massage my ass cheek. I felt so hot with lust, and a bit nervous at the same time. I didn't know whether to let him keep groping me, or scream bloody murder. But, I reminded myself why I came out. To be fit, maybe not now. To get lucky? Well, hopefully.
"It's okay. It doesn't hurt so much now."
"No?"
"Nope," I said. "In fact, I kind of like what you're doing to my ass."
"Do you? You like getting your ass groped like this, baby?" His touch suddenly got a little rougher. I was enjoying it. I let him know that after I let out a little "Ohhh" from out of me.
"Damn. You transvestites and crossdressers sure know what you like," he said, all while he grabbed my ass harder.
"Yeah? You know what we like?" I asked him in my sexy voice.
He got behind me, placed his hands on my thighs, and whispered in my ear, "Yes, sexy. I know what you t-girls like. And I know you want it badly."
He started to peel my bellbottom yoga pants down to about the middle of my ass, exposing my white thong. He pulled my thong up a little bit, giving me an unexpected wedgie. It felt so good getting my thong pulled up like that. I leaned my head back and asked him to do it again.
"Pull it up, you dirty boy!"
As he pulled it up again, I felt my asshole burning. It felt so good, I begged him to do it again by pushing my ass against his hard cock.
"Damn, you are getting really freaky now."
"You started it!" I said accusingly.
"I know. And I will finish it," he said, as he gave my thong one hard pull that made me squeak.
"You better finish it, or I will be on your ass all night until you do!" I threatened.
I moved my hand down towards his bulge that was just urging to pop out of those pants. I unbuttoned his fly and pulled out his long dick, already wet from his pre-cum, and started to stroke it from behind me.
Through the fog I spotted a tree wide enough to hide ourselves in so that nobody saw us. I pointed to the tree and said, "Let's go over there. I want to suck your cock behind that tree."
"Sure," he whispered while he rubbed his cock against my ass crack. Oh, how he was itching to get it inside me. I wasn't going to let him just yet.
Once we got to the tree, he grabbed me from behind and started teasing me with his long cock moving up and down my ass crack. I responded to his tease by moving my ass up and down on his dick. He slapped my ass hard, causing me to moan. He would slap it again, and again. I loved it. I wanted more. He turned me around and pushed his mouth against mine. We started French kissing so passionately, slobbered our mouths to our heart’s content, all while he was grabbed on my ass cheeks, and pulled my thong up my ass harder and tighter.
It sent more shockwaves throughout my body. I moaned really loud into his mouth. He slapped my ass harder. It was hurting so much, but it hurt so good. After about four minutes of passionate kissing, I got down, pulled his pants down and grabbed his nine incher and just started to lick up and down his shaft until he forced it into my mouth. Man, his cock tasted so good. I bobbed my head back and forth a little faster, and the harder he got, the faster I sucked him.
He seemed to enjoy that a whole lot.
"Fuck me, you have really been wanting this for a while, haven't you?" he asked.
"Mm-hmm," I mumbled, as I didn't want to let go of his yummy cock. I was aching for my hole to be fucked by this thick stick.
Before I could ask him to fuck me, we heard another person walking towards us. It was an older white man. He caught us off guard. Apparently he liked what he saw, as he already had his dick in his hand and whacking off to our little sideshow.
"Howdy, fellas! You guys, don't mind me. I'm just enjoying the show," the fella said. He got a look at my ass and said to my new friend, "Man, you sure are a lucky bastard to pull her out of the crowd, huh?"
"She's one-of-a-kind," he replied.
"Just look at how she sucks that thing," said the fella. "Man, I wish my wife sucked me off as good as your lady friend here."
"Hey, uh," my friend uttered before he let out a loud moan and fucked my throat a few times. I nearly gagged. I'm not a deep throat kind of girl. I gag too easily.
"Oh, my gosh. I was about to puke all over you. Don't do that! I don't deep throat. I don't have good gag reflexes!"
"Oh, sorry, baby. Uh, what's your name, again?" he asked.
"Again?" I thought. He didn't even ask me the first time. I nearly laughed.
"Sasha? You forgot, sillyhead?" I said. I had to go with the flow. The fella looked at us like we never met before, which is true. We just met half an hour ago. I looked at the fella and said: "We just started dating. Can't believe he would forget my name after, how many dates?"
The fella laughed. "Haha, I gotcha. Man, the way you're pleasing the man, you'd put any guy in a trance. Isn't that right, buddy?"
"Oh, yeah. You're darn tootin'!" my friend replied, as they laughed, and I continued sucking my friend's cock. It was not long until I heard them introduce themselves and I found out both of their names.
"Darius", my friend said. "Don", the fella replied. Good. Now, I can call them by their actual names.
"Hey, Sasha, why don't you hold off on my cock and help our buddy Don out?"
Don, the fella, was already on his knees and grabbing my ass. He had quite a gentle touch. I raised my ass so he could grope on me a little more.
"Wow, Sasha, you have a nice soft round caboose," he said, admiring it. He kneeled down further and started to kiss all over my ass cheeks. It really made my cock precum at the touch of his lips on my ass. Too bad I can't hit that tonight. My wife will kill me."
I stopped sucking Darius and turned over to Don. "It's okay,” I told him. “At least if I suck you off, she won't know anything. Pussy and ass juices will give it away, but a person's spit can't."
"O-okay, honey. If you're sure about th..."
Before he said another word, I lunged at his thick fat cock and started to suck him. His pre-cum didn’t taste bad. I was enjoying it. Don was getting shaky in his legs, so he said he wanted to lay down while I continued to suck him off. He thought he died and went to heaven when I started to flick my tongue under his cock. It seems to get every guy going when I lick there.
Darius kneeled behind me and kissed my ass cheeks passionately. He moved my thong to the side and pushed his hot tongue into my hole, which sent me to the edge. I loved it so much. The way Darius was tongue fucking my hole caused me to bob my head faster on Don. Darius wasn't done, though. He wanted to fuck me. I put my thong back in the middle and guided him to the hole I cut on the back. He liked what I did.
"Want me to put my dick through that hole in your panties?"
"Mm-hmm," I muffled. After he poked his cock through the hole in the thong, Darius slowly pushed himself inside me. It was hurting. I was feeling the burning of my hole as he continued pushing his fuckstick inside me. It hurt, but I loved how it hurt. I moaned so loud while Don's cock was still in my mouth. Don seemed to like what he saw.
"Wow, Sasha. You sure know how to please men, you little doll. It's too bad you're on your period."
Darius and I laughed. He thought that I was a real woman. I'd hate to disappoint him, though. I just went along with it.
"Yeah, but I don't mind getting it in my ass, too," I told Don.
"Yeah, a lot of you young girls seem to like that more these days, just like them homos. But, that's their lifestyle. Who am I to tell them how to enjoy sex?"
A bit relieved to hear that, I popped his dick out and said, "Exactly. Me, I love it both ways. But I always love when a man comes inside me, regardless." And I went back to sucking Don's dick faster. Darius' poundings got harder and Don was about to reach his peak. Because as he heard me say those words, he cried out, "Oh, honey, what I would do to fill up that pussy of yours.