A New Life

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Bennie, age 21, lived on his own for the first time in his life. It was his first night in his new apartment. He had lived with his parents, Joanna and Chris Smart until just today. This was the start of a new life in many ways for him.

Bennie, or Ben as most people called him, worked as a telecommunications tech for a local phone service. It was his first real job, and he made good enough money to pay his rent, his car payment and still have money left for food and joys of life. His apartment was a one bedroom, one bath apartment, meaning it was two rooms with a separate bathroom and closet.

His parents had helped him move his few things in, like his bed, television and a dinning table set. It came with a fully furnished kitchen and he had cable TV too. Bennie was so excited to be on his on, especially since his parents couldn’t tell him what to do anymore. Ever since he was about 7 or 8, he had been fixated on women’s feet and what they wore.

No matter where he was going, Bennie was always staring at women’s feet. He wanted to see if they were wearing socks, pantyhose or wore their shoes or heels bare. To him, a woman in soft colorful socks, or sexy hose was the sexiest thing he could imagine.

When he was very young, Bennie had been in a school play, and he had to wear black tights with his costume. That one single event in his young life, changed his life forever. He didn’t know it then, but just a few years later, he would find himself wanting to wear them and girls socks. His parents never understood, and always said it was a sign you were gay if you wore women’s things.

By the time he was a teenager, Bennie was sneaking his moms socks and pantyhose when he was home alone. His favorite socks were his moms bobby and knitted knee socks. They were so much softer and prettier than the plain white ankle or crew socks his mom always bought him. She was a nurse, and so had several pairs of white and tan pantyhose, and he would sneak those she decided to trash because they might have a ladder or snag in them. He couldn’t help the way he had felt, he didn’t see why it was so wrong.

Now that he was on his own, he hoped he would be able to get up the nerve to go out and buy his own things and wear them in his apartment. He had gotten caught several times over the years by his mom, and the last time was just a few days ago. He was at work, and for some reason she looked in his dresser, and found his stash of pantyhose and socks. Some were his moms, and a bunch he had bought at the local superstore.

She had told him she didn’t care what he did anymore, but if he wanted to dress like a sissy, and act like one, he needed to get his own place. His dad told him the same thing, and so that’s what he did. They still loved Bennie, but couldn’t take his habits or his fetishes. Bennie decided it was his time to get out on his own, and with help from friends, found this low rent apartment, and got moved in.

Bennie was a slender, very light skinned young man who was never into athletics. He was more into computers, and in high school he took homemaking and even cosmetology. He weighed 160 pounds, had shoulder length auburn hair, and stood about 5 foot 9. Bennie wasn’t muscular, but he wasn’t fat either. He was just sort of toned, and sometimes looked as if he was sick because of his skin tone. His body had little body hair, and penis was about 5 inches long and thin.

Sitting in his new home, Bennie unpacked his clothes putting them away. Being off for the weekend for his move, he didn’t have any plans on what to do the next three days. He needed to go shopping for food and maybe a few things for his apartment. His parents had bought him a few toiletries, and had given him some groceries from home that they weren’t going to eat.

Bored and feeling a bit hungry, Bennie decided to go to the store and have a bite of lunch. His car was an old beat up 4 door Toyota Camry, 1992 model that had well over 200,000 miles on it. He had received it for his 19th birthday, and loved his old car. It had a great cd player, and great a/c and heater.

Once at the store, Bennie eat in the deli first, having nachos and a hotdog. While sitting there, he saw this young lady come in wearing short, a t-shirt and sneaker, and like most girls of today, was wearing mix-matched no show ankle socks in bright fluorescent colors. Those were a favorite of his, cause he could wear them most anytime without others seeing him wearing them. After her, three women who were together walked into the deli, wearing skirts and blouses, but they were wearing flip flops and sandals. That always disappointed him, even though he loved pretty feet. They had cute feet and toes, but he would rather see them in socks or pantyhose and heels.

After finishing his lunch, Bennie decided to go browse through the women’s clothing section. He grabbed a shopping cart and acted as if he was doing his normal everyday thing. Once in the women’s apparel section, he right off picked up three bundles of no show ankle socks in bright colors. He mardin escort then grabbed two six packs of slouch and bobby socks in different colors. Bennie had small feet, so it was not hard to find socks and shoes in women’s or girls sizes he could wear.

Looking around a bit more, he found the sexiest socks he had ever seen. The only time he ever saw them, were in porn movies on usually the teen girls and sometimes cheerleaders. He picked up 12 pairs of lace trimmed anklet socks in pastel colors and regular colors. Before he left the women’s section, he picked out several packs of pantyhose, stockings and a garter belt and stocking set. He was feeling better already, and hadn’t even paid for them yet.

On his way to the grocery section, he saw the area for panties, bras and lingerie. Unable to resist, Bennie ended up buying several thongs, bikini style panties and several matching bra and panty sets. Now if he could just get out of there without looking like a pervert.

After buying what groceries he though would get him by, he went through check-out. The cashier smiled and looked at him, as she bagged up all his food and the girly items in his basket. Before he was out of there, he had spent almost $300, and probably half of that was in women’s things.

Back home, he put away all his food and new clothes. He had gotten quite sweaty while out and about, so he decided to get a nice shower and try on some of his new things. Once out of the shower, Bennie dried off, and began to look through his new purchases. He had felt like everyone in the store had been watching him while he shopping for his sexy things. He almost ran out of the store and come home several times.

Once he was done with putting away everything, Bennie decided it was time to get comfy in his own way. He stripped off his grungy guy stuff, and got into a hot soothing shower. He had picked up feminine body wash and shampoo while shopping earlier. It felt so good to wash and cleanse his body of the male scent he hated so much. Once out of the shower, he decided to shave his legs, using a disposable razor he picked up at the store. It took a while to do, but all in all he thought it looked ok for his first time. Using some lotion, he rubbed his bare legs and his feet, making them soft and feel better.

When he felt he was ready, Bennie pulled out a sports bra and panty set in pink. Putting the bra on first proved to be the most work. After he got it on, and looking right, he then tucked his penis between his legs and pull on the matching pink bikini panties. Feeling pretty and rubbing his hands over the bra and panty, Bennie took out a brand new pair of white control top pantyhose. While was supposed to mean purity and innocence, and that was how he felt dressed like this. Opening up the package, he stretched the pantyhose a bit, then slowly began to put them on. As he slid the smooth nylon up his newly shaved legs, the feeling made his cock twitch and throb between his legs. Pulling them up around his waist, Bennie smoothed out the nylon, and made sure he had them pulled all the way up. Bennie went over to his full length mirror and observed himself. He looked beautiful in his eyes, and wondered if anyone else ever would look at him the same way he saw himself.

Walking around in his pantyhose and underwear, Bennie felt like he was in heaven. He looked in his dresser, and took out a pair of hot pink super scrunchie slouch socks. Putting them on just made him even hornier and he had to do something about it and soon.

“I wonder if there are any places for people like me to go?” Bennie thought about it as he walked around feeling his cock strain to get free from its confinement. Deciding not to chance it, he opened up his laptop and searched the internet for any possible ideas.

After looked through several different pages, Bennie came upon a escort service online that catered to anyone and everything. They advertised it didn’t matter who or what you were, they did it all and at a really low cost. Bennie signed up his account online, and decided to see what he could get for his first encounter.

Looking through the pictures and profiles, Bennie come across a beautiful Asian girl who was a bit older, loved kinky sex of all kinds, and loved to suck cock. He was instantly in love with her profile, and she looked as hot as she sounded. Her screen name was Maya, and she stood about 5’5. 130 lbs, long black hair to her butt, long legs that loved to be kissed, and 38D tits. Bennie almost came in his panties right then as he read about her massive titties.

Calling the number provided, Bennie asked if Maya was available. They informed him that she was, and that she was one of their most sought after girls. He asked how much she charged for her services, and they told him it all depended on how long he wanted to play.

“Well to be honest, I don’t know. What is a normal length of time someone requests for these sort of things?” Bennie felt stupid asking them these questions, but it was his first time and marmaris escort he had no idea what he was doing.

“Well sir, Maya normally doesn’t go out on a call for less than 2 hours. Her time is very valuable and she has to know its worth the trip.”

Bennie thought about it, and after looking at their rates as they suggested, he knew he could afford an overnight stay if Maya was available that long.

“Of course, and according to your information, it should only take about an hour for her to get to your home. ” The operator thanked him for choosing their service and asked if there was anything else he needed or an questions he had.

“Ummm, no I don’t think so. Oh! Do you know if she minds if I ummm like to dress like as a girl or pretend to be a girl while she is here?” Bennie was blushing bright red, even though he was on the phone, knowing he was telling this operator who he didn’t know, things only his parent knew about him.

“Sir, I am sure she will be ok with whatever you want to wear. Maya is a special lady in many ways, and she knows how to take care of her customers.” The operator sounded so comforting to his nervousness and it made him feel better thinking that they might know what he was going through. The operator set up the service and told him to give Maya about an hour to an hour and a half and she would be knocking on his door. Bennie was so excited, and so nervous, that he almost peed himself thinking of what was to come.

While waiting for Maya to show, Bennie put on one of his new pleated tennis skirts, and a lace camisole so he would be dressed for her arrival. He didn’t know what he was going to do with her, but he hoped she would do things he always dreamed of, especially since he was still a virgin and had only jerked off looking at porno on the internet.

It seemed like hours, but then it finally happened. There was a gentle knock on his door, and it startled Bennie as if he wasn’t expecting anyone.

“Who is it?” Bennie listened for the sound of his escort outside his door.

“Hello, im Maya, I am here from the escorting service that a Mr. Bennie Miles called for.” Maya stood outside the apartment door a little frustrated at being made to stand outside.

Bennie opened the door, to the most beautiful site of his life. There stood Maya, his dream girl, in a black sequined mini dress that showed off her sexy long legs and barely held her gorgeous breasts. She was wearing the tallest spiked heels he had ever seen, and her cute little toes peeked out through the little opening in them.

“Please come in, I am sorry, you startled me. You got here sooner than they said.” Bennie showed her over to his sofa and waited for her to take a seat. “Can I get you something to drink? I have water, tea or soda.”

“No thanks, I am fine. Please come sit next to me and tell me about you Mr. Miles.” Maya looked at him with a pretty smile, and knew he was very nervous. Bennie sat down almost on the opposite side of the sofa from Maya and tried to talk, but stuttered in his response.

“Just relax, I am here for your pleasure, and will do nothing you don’t want to do. You are very pretty in your outfit.” Maya scooted closer to him, putting her hand on his pantyhosed leg. He was shaking under her touch, but he loved being so close to her.

“I….I….have never been with a woman before. I don’t know what I am supposed to do, but I know I like what you are doing so far.” Bennie looked at Maya as she leaned in close, inhaling her scent. She smelled of lilac and kind of like fresh rain water. Her scent made him feel intoxicated, making him feel light headed. Her lips were a beautiful deep red color, and glistened with her lipstick. Bennie wanted to kiss her so badly, but was afraid to make the first move.

Maya seeing his reluctance, made the first move and pressed her lips to his kissing him softly and deliberately. He smelled of fresh bath soap and body wash much like that she used herself. Bennie was adorable and Maya really liked him innocence. It was a nice change from the horny, wham bam thank you ma’am guys she normally got stuck with. Feeling him relax more with her kiss, she laid him back on the sofa taking his hands and put them on her body.

Bennie felt so out of place with the gorgeous woman kissing him and when she laid him back on the sofa, he thought he had died and didn’t want to wake up. His hands were on her body, and he touched and felt every part he could. He loved how her dress hugged her figure, and allowed him to feel her breasts and hardening nipples as they continued kissing and making out. Kissing Bennie, made Maya’s pussy wet, and she couldn’t help rub her lips with her index finger as he felt her up. She started to kiss her way down his body, lifting up his cami and bra as she licked and sucked on his nipples. Bennie was moaning and groaning as Maya did things he had only dreamed of in his wildest fantasies.

When she lifted his skirt and licked and tongued his cock through the pantyhose and panties, nevşehir escort she could taste his pre-cum leaking through the material. Knowing he was a virgin, and not wanting to make him cum too quick, she kissed down his legs and pulled off his socks to sucks and lick his toes through the hose. Bennie was squirming all over the sofa, in a world of complete bliss. Maya knew exactly what she was doing, and he hoped she never stopped.

“Maya, please let me, ummmm, you know, taste you.” Bennie had a look of a lost puppy dog as he asked her to let him eat her pussy. Maya smiled, standing up and pulled her dress up over her head and dropped it on the floor. She hadn’t worn any panties, so all she had on was her heels. Kicking them off, she climbed over Bennie settling her dripping wet snatch over his face as she pulled his dick free from the confines of pantyhose and panties. When his cock sprang free, she caught it between her pouty red lips and began to lick and tongue the tip and peehole as he pushed his inexperienced tongue up her pussy.

“Ooooh Bennie, see that little nub right there, at the top, lick and suck on it. Oh fuck yes, just like that!” He may be a virgin, but her was a quick learner. Maya was squealing in delight as Bennie worked his tongue around her clit and pussy lips. She sucked his cock loving the feel and taste on her lips and tongue. To her, there was nothing like tasting the cum of a virgin cock.

Within minutes of starting, both Maya and Bennie were crying out in intense orgasms. Maya squirted her pussy nectar all over her lover, and Bennie almost drowned her in his cum shower. They both jerked and shook uncontrollably on the sofa as they rode out each others orgasms. When they both had calmed down, Maya moved around laying next to Bennie, holding his head to her breast as he tried to calm his breathing.

“Are you ok love?” Maya was holding him close, his body still trembling in her arms.

“Y…yesss I am ok. I have never felt anything like that in my life before.” Bennie snuggled close, and couldn’t stop himself from licking and tonguing her nipple as they lay together.

“Oh it gets better sweetie. Wait until you actually get to fuck me and feel my pussy wrap around that hard cock.” Maya smiled as he moaned at her words. She reached down and found his cock to still be rock hard, and ready for round two. “Do you think you are ready for the ride of your life?” She kissed his lips softly as she stroked his throbbing cock slowly.

“Oh Maya, I so want to fill your pussy and ass with my cock. The only thing is, I don’t have any condoms.” Bennie looked into her eyes with a worried smile, not knowing what her reaction would be.

“Oh don’t worry Bennie, I cant get pregnant and I want to feel that virgin cum inside my holes.” Bennie’s cock twitched in excitement in her hand when she mentioned him cuming inside her pussy and ass.

Rolling Bennie on his back, Maya climbed on top settling her pussy right over him, and lowered herself slowly down onto his cock. His cock wasn’t the biggest she had ever had, but for some reason it touched a spot inside her that made her almost go wild. She rode him like a bucking bronco as Bennie reached up and pinched and twisted her hard nipples. Bennie could feel her pussy muscles squeezing his cock like a vise, and it made him fuck up into her from underneath. He didn’t know what overtook him, but without realizing what he was doing, he rolled over on top of Maya and began to fuck her hard and deep.

“Oh fuck yes, yess Bennie fuck me hard and deep.” Maya was lost in complete ecstasy as he pounded her the way she liked it. Bennie, urged on by her dirty talk, lifted her legs over his shoulders and began to give it to her like he saw the actors do in the porn movies.

Before she knew what was happening, she was having multiple orgasms that never seemed to end. She cried and squealed like a schoolgirl as Bennie pounded out 20 years of virginity into her horny body. Bennie loved the way she moved and cried out each time she came all over his cock. He couldn’t stop if he wanted to, and he definitely didn’t want to. The whole apartment smelled of wild ecstatic sex. He hoped they weren’t making too much noise for his neighbors. This was his first ever time for sex, and he was having the time of his life.

Stopping him just long enough to catch her breath, Maya turned over and got on her hands and knees. “Fuck me from behind Bennie. I want you to ram that hard dick of yours right up my pussy until I make both your balls explode deep inside me.” Maya wiggled her ass in his direction, moaning as she slapped her own ass and knew he was going to fuck her so hard and deep.

“Oh Maya, I want to fuck you so good, that when we are done, you want be able to walk for a week.” Bennie moved in behind her, and pushed himself deep inside her in one hard thrust.

Maya gripped the sofa with both hands as Bennie fucked her with everything he had. She never expected to get this kind of fucking from a cross-dressing virgin who had just moved out on his own. He seemed to be able to go forever without shooting his cum inside her. Just when she thought she couldn’t take much more, Bennie pulled out all the way, then rammed back inside her frantically screaming out, “oh im cumming, oh my god I am cumming!”

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