The Traveling Crossdresser

Will Hamlett traveled alot. As a sales rep for a small firm he found himself constantly on the road to meet potential clients. Life on the road didn't really bother him, in fact he rather enjoyed it. Traveling long distance away from friends and family gave him the freedom and animity to explore every deviant sexual desires.

Today he was traveling to El Paso, Texas. The trip would take a few days, but he was optimistic that he would find a way to entertain himself.

The first few hours was rather uneventful and dull, but then fortune smiled on him. Driving down a particular desolate part of the I-10, he saw a hitchhiker.

She was a pleasantly pump latina girl. Large hips with a big ass that was a little on the flat side, but still looked great in her jeggings. She had on a tunic style top that hid her belly but was lowcut enough to accentuate her small breasts and maybe even make them appear a little larger then they actually were.

As he pulled over to pick her up, she cautiously approached his car. Rolling down the passenger side window, Will smiled and asked, "Where you headed?"

Peering into the car, she saw Will, a middle aged man with a small build with a wedding band. The car was clean, his dufflebag was in the backseat. Not getting creeper vibes and being desperate for a ride, the young Latina said Las Cruces or as close as you'll take me. I'm Maribelle by the way."

"Well, I'm not headed quite that far," Will lied not wanting to commit his whole trip to the first hitchhiker he saw "but I can take you to at least Wilcox. That's at least civilization. Come on and get in. You can tell me how you wound up in the middle of the desert."

Maribelle got in and she explained how her now ex-boyfriend were on the way to Las Cruces to see her family when they got into an arguement. Maribelle had picked the worst time to confront him about his side piece, because he literally kicked her to the curb with nothing and drove off.

The next two hours to Wilcox was filled with pleasant conversation. Will told Maribelle about his wife and the kids, and Maribelle talked about her family. Eventually they got to the edge of Wilcox. Pulling into a gas station that didn't seem like it saw a lot traffic, Will stopped to fill up. As he pumped gas he saw that Maribell hadn't made movement to signify that she thought this was where he was going to drop her off. He smiled to himself, as he hung up the pump.

Getting back into the car, he announced, "Well... this is Wilcox. It has been fun, but it's time for us to part ways. " Maribelle glanced around the desolate parking lot, and meekly asked" Here? you couldn't take me a little further?"

"Sorry, this is the end of the line. You're kinda cramping my style. See usually on my business trips away from the wife I like to watch porn on my phone and jerk off on the drive. I can't do that with you in the car. So basically I need you to get out so I can whip it out. "

Looking around the empty parking lot, and not seeing any good options, Maribelle pled her case. "Listen just the next major gas station, please! You can watch whatever you want and do whatever you want to yourself. I'll just sit here and go along for the ride."

Will pretended to think it over. He was betting on her making this offer, because he hadn't really left her any other choices. Reaching for his phone, he set down the ground rules if she were to continue to ride with him. 1. He wasn't stopping at another gas station until he needed gas. 2. She didn't have to participate, but she had to watch. 3. She couldn't have her phone out, to ensure her undivided attention and that she wasn't taking pictures. Maribelle reluctantly agreed to the conditions and they drove off.

Once they got back on the interstate, Will linked his phone to the car's bluetooth. He then had the arduous task of deciding on what porn to play. He wanted something that would make Maribelle uncomfortable but not scare her. So rape and BDSM porn was out. After careful consideration he decided on what they were going to watch.

Pushing play on his phone's display the car stereo boomed "Sissy faggot worship cock like the cock slut you are" Video clips of transwomen and fem boys being force fed huge dicks played on his phone, while his car stereo continued with the sissification mantra. Caught off guard, Maribelle looked questionally over at Will.

"What are you some sort of fag?" Will just smiled and undid his belt. He pulled his pants down mid-thigh exposing his pink boy short panties with a small bulge.

Seeing his pink panties, Maribelle exclaimed "Ewww, you are a homo! You're a fucking faggot! You're married too!"

The verbal assualt was a huge turn on. Precum began leaking out of his cock, putting a wet stain on the front of his panties. Will began rubbing his bulge with two fingers, explaining," I like cock every once in a while. If that makes me a fag, then I'm a fag. My wife would never understand, so that's why I enjoy these car trips so much. Do you like my panties? Do you want to see my cock?"

"No!" shrieked Maribelle. " I'm just here because I need a ride. I don't want to see your cross-dressing faggoty ass dick."

"Too bad, we agreed you would watch." With that he pulled his shaved cock and balls over his panties waist band. The band pushed his balls up his shaft making his small semi- erect penis look even smaller. From Maribelle's point of view it only looked to be about an inch and a half. Will began stroking his nub with just his thumb and forefinger.

"It's tiny! You had three kids with that little thing! That is so gross you fucking freak. You're so gay! You're literally jerking off to girls who have bigger dicks than you. Do you want to be one of those girls and suck cock, you fucking faggot? Or do you like to pretend you're one of those hung guys fucking them?

Does that little thing even cum? Eww don't you dare get any cum on me!"

Unknowingly, Maribelle's was providing Will with the verbal humiliation he usually had to pay for. He pushed his panties down a little so that he could get a grip on the full length of his erection. He began frantically tugging on all three inches.

It was difficult trying to drive, watch porn, and make eye contact with Maribelle all the while beating off, but Will was determined to nut.

Suddenly a trucker passed him on the right and blasted his horn. Startled Will looked over and saw the semi-driver smiling and pointing at a road sign. Looking back at the road Will barely saw the sign as he passed, "look out area no services 1 mile"

Perfect. Will pulled up his panties and pants and got over in preparation to pull off. Not understanding what just happened Maribelle was confused. "Aren't you going to finish? I don't care, it's just weird that you stopped. "

Ignoring her, Will pulled off to the lookout area. behind the trucker. Expecting the worse Maribelle panicked. "You said I wouldn't have to do anything. This is rape, don't you come near me with that little dicklette of yours! I'll scream!"

"Relax, I'll be back. If you don't want to wait find a new ride... I don't care. Just lock the doors if you leave. " With that Will parked the car behind the semi and grabbed his duffle bag and got out. The trucker had already started casually waking. Without another word to Maribelle he started following him down a well beaten path into the treeline.

Thirty minutes went by, and Will still hadn't returned. Maribelle tried to find another ride, but besides Will's car the only other vehicles at the overlook was the semi and a mini-van. Both of them were empty with the drivers nowhere to be seen. Frustrated Maribelle started down the trail to find Will.

She heard men's voices in the treeline where Will had disappeared into. As she approached she could make out what they were saying.

"This bitch loves getting it hard! I can't pound this sluts ass hard enough. Ain't that right bitch. you love my fat dick fucking your ass? Answer me whore!"

"mmgfh. I mmgfh it! Uugh!"

"Do you really expect this cocksucker to answer you when I got my cock shoved down her throat? Come on baby just a little deeper. Stick your tongue out and lick my balls. "

Maribelle approached as quietly as she could. Hiding behind some bushes she got a clear view of what was taking place... She couldn't believe what she was seeing. There was two men in the clearing with Will. Will had apparently changed into some Britney Spears school girl outfit with a Taylor Swift style cardigan. He had a blonde wig on, but it was definitely him. He was bent over. His skirt was flipped up and his boy shirt panties were pulled down to his knees. The trucker was behind him pumping away. He was a fat hairy beast of a man. Every thrust of his hips caused beads of sweat to fall onto Will's back. His belly fat jiggled almost as much as Will's tiny little cock which was flopping widely as his ass was assaulted by this nasty pig of a man.

The third man stood in front of Will. At first Maribelle thought he was fully dressed, shirt, tie, dress slacks, nice shoes, and a bright gold wedding band. He had a tall athletic build with smooth chocolate brown skin. His large hands held Will's head down on his crotch. Only his balls were exposed from the fly of his pants. The rest of his cock was in Will's throat. Will's eyes were bulging and his cheeks were turning red. Slowly the well dressed man pulled his cock out, inch by inch. After the first seven inches came out, Will stated to cough and gag. The last three inches of that massive dick was covered in a thick coat of saliva and mucus.

Will struggled to catch his breath and regain his composure, grasping the black man's muscular ass for support. Rather then sympathy, Will got his face slapped by 10 inches of dark meat, all the spit was wiped off on both of his cheeks before his mouth was stuffed once again. This time however rather then holding his head down, the black man held Will's head still as he forcibly facefucked him.

Maribelle couldn't believe it, were all married men secretly gay? Why would that beautiful black man with the biggest cock ever fuck a loser like Will. He could pick up any girl he wanted, why hook up with a cross-dressing fag? As she watched his huge penis slide in and out of Will's throat, she could feel her panties getting moist. As her hand slid down her panties, she closed her eyes and imagined she was getting that big black cock.

Mid thrust the trucker stopped and whispered "What was that? I heard someone." All the men stopped. Gentle moaning was coming from the bushes. The black man popped his cock out of Will's mouth and walked over to investigate.

"Well. well. well who do we have here? Do you just want to watch or do you want to come and play?" He exclaimed as he found Maribelle on her back, eyes closed, finger banging herself in the bushes. Startled Maribelle sat up only to come eye level with his long erection coming out of his pants. Speechless her jaw dropped at the sight.

Without missing a beat the man moved his cock closer to her lips. She couldn't believe it, but she found herself leaning in towards his monster cock. She greedily gobbled as much down as she could. She took about half of it before choking.

"Tsk, tsk not here little girl, " he said as he pulled his dick out of her hungry lips, "over there with everyone else. " With that he grabbed a fist full of her hair and dragged her over to the other men.

"Maribelle? What are you doing here?" Will asked shocked.

"Looks like she's looking to get dicked, and I got a fat one for her," the trucker said as he pulled his cock from Will's ass. His cock was a lot like him; fat and hairy. It was probably 6x6 uncut with hair going half way up the shaft. It looked like a beer can.

What was happening Will thought? Will went from having two dicks in him to none. He wasn't happy. He had gotten dressed for the trucker. Right when the trucker started fucking his sissy school girl ass, the married black guy came by and spit roasted him with the trucker. Now this dumb slut Maribelle was taking all the attention.

"No way!" shrieked Maribelle,"You are not touching me with that nasty shit dick, fat ass. As for you Will your little girl dick couldn't fuck anyone look how tiny it is " With that she grabbed his Will's dick in one hand and the black man's cock in the other. "If I'm getting fucked its going to be by a real man with a clean cock."

"My cock is clean! Look this dumb bitch is sucking all his ass juice off it" exclaimed the trucker, as he shoved his cock into Will's mouth. Happy to be getting cock again, Will began sucking passionately.

"No thanks, Pappi will you fuck my pussy please?" Maribelle pulled her jeggings down just below her globular ass cheeks and gave an enticing bounce. The black man wasted no time and walked over and pushed everything he had into her. It wasn't long before he was hitting it so hard, Maribelle had to get down on all fours to take it.

The trucker although disappointed he wasn't going to get a chance to fuck Maribelle did the next best thing and fucked Will right next to her.

Will's ass was tight. The only lube the trucker was using was spit. it wasn't long before he erupted inside of Will. As he pulled out the last rope of cum shot out and dribbled down Will's leg into his panties. Will turned around and sucked the truckers cock clean while the trucker wiped the sweat from his brow.

Then together they watched Maribelle's pussy get stretched by the black guys massive cock. Will stroked his little erection as he watched.

"Come here bitch!" The black guy called over to Will. Will dutifully came over. The black man was on his knees pounding Maribelles pussy and now was simultaneously sucking Will's dick.

"What are you doing! Don't suck that faggots dick, what are you gay?" Maribelle turned and said to the black guy right as Will came in his mouth.

"Bitch,shut up I ain't gay" He said and spit all of Will's cum in her face.

"Ugh get off me faggot! I can't believe I let you fuck me!" Maribelle screamed as she tried to get up.

"Where are you going? I'm not done whore." Straddling her chest the black guy pinned Maribelle down and proceeded to jerk off and nut in her face.

"Now I'm done, whore. Thank you, but I need to get home to the wife. "

"Argh! Fuck you, Will, let's go!"

Will looked at Maribelle. Now that he came he really didn't want her around. He looked at the trucker and asked, " Can you give her a ride, please. I'm not really going her way. "

The trucker smiled and replied, "Ass, cash or grass little lady. "