The walk home, Danny meets someone

Danny stood on Jessica’s doorstep afraid to move. He had his black shoulder strap purse (his purse? Omg I have a purse!) clutched in both hands in front of his waist as his eyes darted around him looking for someone. He was terrified, looking for someone to call him out as a man in a skirt, but no one was around. He started to calm down, realizing he was alone in the night.

“Ok Danny. You got this. You’re out of that lunatics apartment and free to go home! Sure, you’re in a skirt, wearing a corset, with sky high pumps on your feet and an infernal butt plug up your ass, but you’re free! Now get your ass moving and get home to get out of this shit” Danny thought as he took his first steps towards home, hearing the click-clack of his heels on the pavement cause him to shudder again at his predicament.

The warm late spring air felt great on Danny’s exposed skin. He was surprised how nice of a feeling the warm air felt flowing under his skirt. Danny scolded himself. The swinging of his loose mini skirt did feel nice on his exposed thighs. And the thigh high white socks still felt great on his glossy legs. Now that he was free from Jessica’s wicked clutches, he could admit that some of the clothes felt…. Well good actually. And the plug, while making him feel very very full, was prodding at his prostate with each rotation of his hips. “Stop it, Danny! You don’t like wearing a skirt! This is the last time! Youre not gay, you’re not gay, you’re not gay!” Danny tried reminding himself as he felt his little member start to waken up in its cage.

Danny tried to make his way quickly through the darkened campus. Streetlights lining the paved walkways between the full green trees. At almost midnight on a Tuesday, the campus was basically empty, and Danny was very happy that was the case. He kept his eyes peeled, searching back and forth as his pony tail whipped from side to side looking for anyone coming up on him. But Danny was alone, only having the sensuous feeling of his girly clothes, the click clack of his heels, and his own thoughts questioning his reality to himself.

Danny came upon a cross street and was waiting for the signal as a car slowed to a stop behind him. “Shit shit shit. Come on keep going please!” Danny pleaded but saw the light turned red and the car stopped. Afraid to look, Danny kept his eyes down towards the ground not wanting to make eye contact.

“Hey! Hey girl! Whatcha up to tonight looking so good??” A masculine voice called out.

“Fuck. Fuck fuck fuck. No come on light turn please!” Danny thought. He tried to look surreptitiously at the car and driver. Hanging out the drivers side window and back window were two college boys. Fairly attractive in their own right (I’m not gay I don’t find men attractive, Danny thought), both the brown haired white boys looked like any number of attractive college hunks on campus.

“Hey baby it’s alright. We just wanted to see what you’re doing tonight. If you want, let me get your number and we can meet up?”

Danny turned and looked at the boys, realizing the little sedan was packed full of college jocks. Each of their gaze was filled with lust as they hungrily looked up and down Danny’s feminine body. From his pink stilettos up his white socked legs to his tiny pleated skirt, up his thin corseted waist, stopping for a long time on his enhanced chest, the horny boys undressed him with their eyes. Blushing at the shame of not just being undressed and ogled, but that they seemed to have no clue that Danny had a male appendage between his thick thighs. Before Danny could answer, or do anything else, the car behind the boys honked as the light turned green.

“Shit, alright girl well here’s my number. Hit me up ok? Names Jason, cutie!” The driver said as he threw a piece of paper, hitting Danny right in the cleavage before bouncing to the ground behind him. Without thinking, Danny turned and bent over to pick up the paper. Still stuck in his girly practice with Jessica, Danny bent at the waist, giving the boys a great look at the bottom of his pronounced butt cheeks under his skirt, the pink thong barely visible between his girly cheeks. Danny heard multiple whistles and a “daaaaammmmnnn that girl has an ASS!!!” Before another honk caused the boys to drive away.

The shame of what he’d just inadvertently done, showing off for that car full of boys, brought another flush to his cheeks. He snapped back up, holding his hand to his mouth as the reality of his slutty pose hit him. “Damnit, Danny! You’re not some slut you’re a man! Get it together!” Danny scolded himself again as he continued his trek home, unconsciously slipping the paper with the boys number on it in his purse.

Finally, his apartment was within eyesight and not a moment too soon. His feet were starting to ache from his slutty heels and the corset was really doing a number on his waist. But the plug was really getting to him. Each step **** the plug to run his prostate and he’d begun to leak through his cage. While unable to get hard, Danny was getting hornier and hornier by the minute. “Almost home Danny almost home!”

As he approached the front door of his complex, home almost within reach, he saw a man leaving. And not just any man, a large black man, none other than his roommate, Demarcus. “Shit shit shit! No please no! Ok just walk away and wait for him to leave” Danny thought as he turned on his heel to do just that. But, still unaccustomed to his new feminine footwear, Danny turned to quickly and fell on his feminine rear. “Eeeep!” Danny femininely squeaked as he fell on to his butt. Before he could get up, a large black hand was in his face.

“Woah girl! Watch yourself on those stilts! Here let me help you shawty” Demarcus low masculine voice rumbled as he grabbed Danny’s hand. Looking at the stark contrast between the two hands, one black and massive, the other white and dainty looking, Danny again felt a wave of humiliation course through him. As Danny was helped up, the humiliation was made even worse as Demarcus’s put his other big paw on his lower back. Well, very lower back as most of his hand landed on Danny’s ass!

Danny stood back up, his hand still engulfed by his buddy’s massive mitt and his ass still covered in the other. He still felt unsteady on his feet and put his feminine hand on Demarcus’s chest to steady himself, unknowingly flirting with the big man as he stared up at him through his big lashes. He still had to look up at him, even with his 5 inch pumps

Demarcus smiled down at the little brunette white girl. “Damn, getting these little snow bunnies is almost too easy at this school. They practically throw themselves at me. This little bitch can’t stop stroking my pecs either. I fucking love college” Demarcus thought to himself.

Danny was in shock. Here he was, being held by his roommate dressed like a slut. His big hand on his ass felt like a hot iron. He was so humiliated to be seen by his friend like this, he couldn’t let him know who I am. “I gotta play into the role. Can’t let him know who I am. Fuck, this plug is making me so horny. Why’s my cock twitching so hard in this damn cage??”

“What’s your name, cutie? What’re you doing over here” Demarcus asked as his hand crept lower, fully encompassing Danny’s ass.

“Um I’m Dani…elle. Danielle. I’m um, just visiting a friend in the building.” Danny responded in his new feminine sissy voice.

“Oh a friend huh? Boyfriend or girl friend?”

“Oh a girl friend! I don’t have a boyfriend!” Danny quickly responded out of habit to explain he wasn’t gay, not realizing how that would sound in his new attire.

“Oh really? No boyfriend huh? Well maybe we can change that” Demarcus flirted as he brought his hand up to brush back a lock of Danny’s brunette hair off his face.

“Oh um… I… ummmm… maybe?” Danny responded, completely confused on how to respond.

Demarcus took that as an invite, as he bent down to bring his face to Danny’s. Danny looked up at him through his big lashes, plump pink lips slightly opened in shock but looking so inviting to Demarcus. Before Danny’s brain could respond, Demarcus’s manly lips met his pink ones. Danny’s eyes opened wide in shock as he felt the manly lips touch his. The 5 o’clock shadow brushing his cheeks. Demarcuses hand on the back of his head, pulling him into the gay kiss. Demarcus’s big thick tongue pushing into his mouth felt so strange! Danny was used to being the aggressor with a woman and here he was on the other side.

It only got worse as Demarcus’s hand started pawing at Danny’s skirted rear. His big hand was groping Danny’s ass. The groping itself felt good to Danny’s body even as his brain was screaming inside about the **** homosexual act. But what was worse was the plug was being pushed and pulled inadvertently with the manhandling, causing waves of pleasure to roll through Danny’s body. Due to this pleasure, Danny moaned into the kiss, starting to dance his tongue along Demarcus’s. Danny pressed his body into Demarcus, pushing his enhanced chest into him as well as his skirted hip. As his hip pushed into Demarcus’s groin, Danny was further shocked by the massive python he felt underneath Demarcus’s sweat pants. “OMG that thing is huge! There’s no way that’s real!” Danny thought as his hips continued to gyrate, causing the big black snake to twitch and move on its own.

Suddenly, Demarcus pulled back from the kiss, still kneading Danny’s ass. Danny’s eyes were closed, lost in pleasure with his mouth still parted. “Mmmmmmmmmm” Danny moaned.

“Yeah, I think we can fix that boyfriend issue, Danielle. Sorry but I got somewhere I have to be but let’s continue this soon. Tomorrow. Here girl, take my number. I’m taking you out tomorrow. Be here at 8. And as much as I like the chase, I expect you here on time and looking…. Sexy” Demarcus said as he eyed up the cute little white girl in his arms, continuing to manhandle her big ass “damn, this shawty got a phat ass. Not a typical white girl” Demarcus thought.

Lost in pleasure, Danny just rolled with the waves flowing through him. He bit his lip as Demarcus talked, only somewhat understanding he was to be here at 8 tomorrow. As Demarcus stopped talking, his hand pressed the plug deeper into him, cause Danny to gasp. “Yesssssss, sir!” Danny half moaned.

“Mmmm sir. I like that, girl. Why don’t you make it Daddy” Demarcus smirked as he pressed on her ass once again.

Another jolt of pleasure coursed through Danny. “Mmmmmm yessssss Daa-daddy!”

“Good girl. I’ll see you tomorrow, shawty.” And Demarcus left, not before landing a hard slap on Danny’s skirted ass. With a yelp, Danny grabbed his now sore ass as he watched Demarcus saunter away. “What the fuck was that???” Danny thought, shaking his head. He unconsciously smoothed out the front of his skirt and felt a wet spot on the front. Shame coursed through him as he realized how much he leaked precum from the manhandling his roommate just put him through.

“Just get inside and get to bed, Danny. You can fix this in the morning” Danny thought as he strutted into his apartment building.

Unbeknownst to Danny, Jessica sat in her car in the parking lot and turned off the recording on her phone. “God this couldn’t have gone better! Now I have the little fairy making out with his buddy! And calling him Daddy! Fuck I’ve got the little bitch right where I want her” Jessica thought to herself as she surreptitiously touched her own crotch. She’d never been more wet in her entire life. Turning this straight boy into a gay sissy crossdresser was the hottest thing she’d ever done. Jessica stopped herself from continuing as she turned the car on to go home, excited to wake the sissy up in the morning.

Danny entered his apartment slowly, not wanting to have his other roommates see him in such a slutty outfit. Thankfully, everyone seemed to be gone so he quickly pranced over to his room and locked the door behind him. Danny quickly took off his low cut top and skirt. Going to his bathroom, he looked at himself in the mirror. In front of him was a slutty brunette in pink bra and thong, black corset, white thigh high socks and pink platform pumps. Her enhanced chest heaved its cleavage with each tiny breath the corset allowed him. Her ass and hips looked incredible framed by the pink thong and black corset. Danny turned and saw the pink strap engulfed by his naturally large cheeks. He turned back and looked at his crotch where only a small bulge appeared from the cage. He looked at his face and saw a slutty girl, her pink eye shadow glittering behind the large fake lashes. The high ponytail held his big thick brunette hair back behind the cute little headband. The pink blush on his cheeks deepened from shame and humiliation as he saw his pink lipstick smeared from the gay make out session.

Unable to look any longer Danny turned back to his bedroom and tried to get the corset off. It was so tight he couldn’t get his hands behind him to untie it. Try as he might, he couldn’t get a grip on the laces. He tried to get the damn heels off, but they were still locked on tight! With an exasperated sigh, Danny fell onto his bed, exhausted from his evening ordeal. So tired to do anything else, Danny fell into a fitful sleep.