DC Transitions Ch. 01

Story Info
David leaves college and makes a big life change.
6k words
4.59
26.6k
12
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is the first part of a story about David's transition. It includes descriptions of oral and gay sex, shopping, and political intrigue. If you like it, there's more to come.

*****

July 2015

Sara and Alexis left their dates at the dinner table while they went outside to have a cigarette. Neither of them fit the Vogue or Cosmo ideal of beauty, but neither had any trouble getting dates. Sara was taller, 5 foot 11, but she and Alexis were both a size 14 or 16 and loved going shopping together. The thing men instantly noticed about Sara was her chest - 38DD - with deep beautiful cleavage. Although she was big, she had almost no fat. She did barre or yoga almost every day to keep her arms, butt and stomach toned. She could turn heads when she wore a bikini to the shore.

Tonight Sara was wearing a deep purple hammered satin halter top dress. Her arms and shoulders had taken on a summer bronze. She loved wearing this dress out since it showed off her toned arms, and even though it didn't have a deep neckline, the high waist accented her boobs. Plus, she could wear it without a bra, so all she had to do was untie the knot around her neck to give her date access to what he had been staring at all night.

Sara and Alexis smoked their cigarettes and talked about their dates. Sara met Russell Chambers 6 months ago. He was only 30 years old and already chief-of-staff for the chair of the House Ways and Means committee, one of the most powerful men in Washington. Russ was getting ready to run for Congress on his own next year, and as a Republican in a Republican district with the backing of one of the most important men in Congress, he was a shoo-in to be sitting in the House in 2017. Alexis' date Bill also was a congressional staffer, but had a much smaller job for a much less powerful congressman. The girls guessed that Bill was inside trying to kiss up to Russ. Sara knew she'd hear about it tonight from Russ.

Alexis looked at Sara and said "Girl, when you came to DC 3 years ago did you ever imagine this is how things would turn out? A congressman's girlfriend!"

Sara took a deep drag from her cigarette. On the exhale she said "He's not a congressman yet. And if you only knew the half of it!" They both laughed, put out their cigarettes, and went back into their dates.

As she suspected, Russ complained about Bill in the taxi all the way back to his townhouse. Sara rubbed the inside of his thigh and told him she'd make it up to him when they got home. Russ unlocked the door to let them in and they headed upstairs to his bedroom. By the time they got to the top of the stairs Sara had already managed to untie the knot on her dress and slip it off. The purple satin lay in a pile halfway up the stairs. Bill turned around and saw Sara standing three stairs from the top. She was wearing a white satin tanga panty. Her breasts were ample teardrops, with small nipples pointing up towards where Russ stood above her.

She called Russ over to the top step, reached forward, undid his belt, button and fly, and pulled his pants down to his ankles. He was wearing Brooks Brothers blue oxford cloth boxers - the official underwear of the Republican party, Sara thought. His erection was pushing against the front of the boxers, and there was a wet stain of pre-cum about the size of a quarter at the tip of his cock.

Sara pulled his boxers down. She still smiled every time she saw Russ' 10 inch erection. She's drawn like a magnet to men with big dicks, and when she saw Russ she just knew that this was a guy with a "big swinging dick", as the Congressional staffers like to brag. But for Russ it was true.

She took the tip of his penis in her mouth and rubbed the shaft with her right hand and Russ' balls with her left. She heard him moan and felt his legs get shaky. He had been back home in his district for over a week. He apologized to Sara in advance "I haven't cum for over a week. I'm not going to last long and it's going to be a big one."

Sara stuck his whole dick in her mouth, overcame her gag, and started deep throating Russ. She missed the taste of his cum over the past week. As far as she was concerned, the faster and the bigger Russ came the better. She felt him start to throb and his legs start to shake more. He moaned. She pulled back and focused her tongue on the tip of his penis. Russ started to cum, the first spasm sending a huge load to the back of Sara's throat. She wasn't ready for it and started gagging before she could swallow it. She finally swallowed the first load down but couldn't keep up with everything that was coming out of Russ. Cum leaked out of the corners of her mouth and dripped down her chin onto her breasts. She kept Russ in her mouth until the cum stopped and he started to go limp.

Russ' legs gave out. He was standing on the top step with pants and underwear around his ankles. His only choice was to fall backward into the upstairs hallway. He hit the floor and immediately started laughing. He was the one looking up at Sara now, up her long toned legs, past the satin panties, up at her breasts, which were just a beautiful from this angle as from above. A stream of cum had run down onto Sara's right nipple, and a drop was just about to fall, when Sara grabbed her tit and swung it up to her mouth to lick the cum off. Russ felt himself starting to get hard again.

Russ said "Hey - you're not the only one who's going to get to have all the fun tonight. Help me up into the bedroom so I can fuck you Congressman-style."

April 2008

David was less than 2 months from graduation. He came to George Washington University, in DC, because he wanted to study politics, and it was in DC, and he didn't get into Georgetown. Then the economy blew up and most of the kids he was graduating with were going to live back home with no job. David was lucky, he guessed, because he had just gotten a job offer to be an "administrative assistant" at a pharmaceutical company back home in North Carolina. Four years of political science, a 3.8 GPA, and he was leaving to be a secretary. But it paid $45K a year, had good benefits, and was 9-to-5, so maybe he could volunteer on some political campaigns nights and weekends. It wasn't his dream, but it would do.

While he was interviewing for the job over spring break, he looked at some apartments. Now that he had the offer he called the one he liked best to put a deposit down for a June lease. It was in a Raleigh neighborhood that was still cheap but starting to get some cool bars and restaurants. He sure wasn't going to miss GW - he had nobody he cared about keeping in touch with, had only had 2 girlfriends over 4 years, and just sort of blended into the background of all the rich kids in their fancy cars, and the former high school cheerleaders.

He had just broken up with Julie 2 weeks ago, after he came back from spring break. Even now he still finds her amazing. In a sea of rail thin blondes at GWU, she was voluptuous, and carried her curves with style. The first time he met her was in his senior political science seminar. She was in skinny jeans showing off her size 14 ass, a tight low cut blouse showing off her 36D tits, and a flowing sheer scarf. She looked like nobody else on campus, but none of the other kids seemed to notice her. He doesn't know how he didn't notice her for 3 years.

And she had a special skill - she was the Micheal Jordan of fellatio. David was about to give up on girls entirely until the first time Julie blew him. The things she did with her tongue, and the suction she could get on his balls, so much it almost hurt until she would let it go and he'd get a spasm of ecstasy. The first time she blew him it had been the first time a girl had made him hard since freshman year. He realized he needed to be with this girl.

They had a good run for a few weeks - some studying, discussions of progressive politics, fellatio. Sometimes while they were out David would rub Julie's thigh under the table and she would get so aroused that she would have a wet spot on her pants or skirt when she got up. But David never really satisfied her. His dick was maybe 2 inches limp, and with a generous ruler it was 5 when he was hard. Julie would be so wet that neither of them felt anything when he penetrated her. He'd start going limp, pull out, she'd finish him with a sad hand job, and then get her vibrator to finish herself off. He knew when he went away to North Carolina at spring break that she was getting sick of this routine.

When he got back she decided she'd give him one more try. They went to dinner in Georgetown the night he got home and then went back to her apartment. She unzipped his pants and started her magic on his dick. He got hard, and she thought there might be hope, then David started going limp again.

He had to do it if he was going to cum. He had to stop thinking about Julie, and think about the night he had with "Steve" in North Carolina. He knew Steve wasn't his name, he saw the wedding ring and the credit card with another name, and knew that Steve was just a married man in Raleigh on business looking for a twink for a quick fuck. David was cool being that twink - he had done this a few times back in Dupont Circle.

David gave the signs that he was available. He went out to smoke a cigarette and when he came back Steve was in the barstool next to his and there was a fresh drink at David's place. They made small talk and then went back to Steve's hotel room. Steve unzipped his pants and sat on the bed. He made David strip off his shirt and pants. When David dropped his pants, he was wearing a pair of Julie's satin bikinis that he had filched from her apartment. Steve knew he found the right twink and started stroking his own dick through the waistband of his boxers. Steve told David to keep the panties on and get his faggot slut mouth onto his dick.

David pulled a 9-inch erection etched in throbbing veins from the slit in Steve's boxers. Steve had never met Julie, but if he ever did he would thank her because David used every trick he had learned from her. Within five minutes Steve was moaning and writhing, trying to hold his cum load back, but he couldn't, and he shot a huge load all over David's face. When David rubbed his eyes clean of Steve's cum he looked down and saw his tiny erect dick pushing against the satin, with a big circle of pre-cum staining the panties.

He remembered the taste of Steve's cum and his erection in Julie's panties, and as Julie sucked him off he started to get hard again.

That night in North Carolina Steve flipped David onto the bed on his knees and pulled the panties down to David's ankles. He took a bottle of lube off the nightstand and started squirting it into David's asshole. None of the guys David had fucked back in DC had a dick this big. Steve started fingering David while he got hard again, and then when he was hard he pushed the tip of his dick into David's ass. David immediately felt his own dick start to throb, and knew that he was going to come soon. He just needed to hold it until Steve came.

Steve eased himself in, until his nuts were up against David's ass. David had never had a dick this far inside him. It hurt, but in the same good way it hurt when Julie sucked on his balls. Steve pulled out and gave a gentle thrust. David felt a chill run up his spine it felt so good. Then Steve started thrusting. No fancy moves or positions, just David on his knees with a pair of satin panties around his ankles with a married man's throbbing 9-inch penis rhythmically hitting David's prostate and making him shiver. David could feel Steve's dick starting to spasm, he knew the cum load was on its way, and his own dick, barely half the size of Steve's, was about to blow it's load too. As he felt Steve come he let loose his own cum load, putting it all over the comforter on the hotel room bed. It was the biggest load he had released in a long time and he fell down onto his stomach, melting into his own jizz, Steve's jizz leaking out of his ass. He was thoroughly spent.

And that's when it occurred to him - he couldn't cum with Julie unless he put something into his ass. David said "Julie, get me your vibrator. I need it in my ass if I'm gonna cum." Julie, master of fellatio, champion of all causes progressive, lover of all things gay, kicked David out of her apartment for wanting to stick her rabbit up his ass.

But David took three important things from Julie. He saw that a curvy girl could be the sexiest one in the room. He learned how to give a killer blowjob. And he was able to nick 2 more pairs of her panties.

August 2010

David had been in North Carolina just over 2 years. He showed up at work on July 1, 2008 and learned he was going to be supporting 3 mid-level managers in the business development department. When he interviewed in March, the head of the department was Jim McCarthy, who was a 60-ish good ol' boy and gave off vibes of being a drunken lech. When David showed up the first day, Jim was gone and the new VP of business development was a late 40ish woman named Tanya. In the first few days David decided she was no-nonsense, probably a dyke, and got the sense that the easy-going 9-5 routine might be in jeopardy.

It became clear to David that Jim's old executive administrator was an idiot. She was in her late 20s, and other than blonde hair, big tits and a tight ass seemed to have no other redeeming qualities. David went out on smoke breaks with some of the other admins and they speculated that Jim's old admin had only 1 responsibility - fucking Jim. By August 1, Tanya had gotten rid of the bimbo and David was promoted to being Tanya's executive admin. With that he got an extra week of vacation and had his pay bumped to $60K. Even if Tanya was a mean dyke, he could live with that.

Before moving to North Carolina David had decided to make 2 big life changes - he wasn't going to deny he was gay anymore, and his days of wearing men's underwear were over. He wore a pair of Julie's bikinis to graduation, the first time he had worn a pair all day. That's when he realized that as round as Julie's ass was, her panties were too small for him - he was picking them out of his ass all day. Julie's panties were XL from Victoria's Secret. He felt so sexy in them but went to VS online and saw they didn't have any bigger sizes.

After he got to North Carolina he decided to do some panty shopping. The first hit for "plus size panties" was Cacique - he clicked through and was amazed to see all kinds of sexy panties where size 12 was the SMALLEST size. And they had a sale with 3 for $30. He figured he must be about a size 16 and ordered a lace and satin hipster, a satin thong, and a microfiber hipster.

Five days later the panties arrived and he couldn't believe how sexy and comfortable the panties were. He could tuck his small dick into the crotch of the hipsters and have a flat front with a hint of camel toe. The day he got his first paycheck he went back online and ordered 15 pairs. He ordered hipsters to wear on normal days, a few thongs for nights out, and a beautiful white satin bridal tanga for really special nights. He couldn't wait for the package to arrive.

Over the first few months he ordered more and more lingerie. He measured his chest and according to the size chart he needed a band size 40 in bras. He ordered D cup breast forms. Cacique ran a sale, buy 2 bras get 2 free, and he ordered 4 size 40D bras: two satin plunge push-up, a 6-in-1 strapless, and a satin demi. He waited every day until the packages came. The bras came first, and they fit around his chest perfectly, but he still didn't have anything to fill the cups. Two days later the breast forms came. He put them in, expecting to have a chest just like Julie's, but something was wrong. His new D-cup boobs didn't fill the cups. He looked like he had saggy old lady tits. It didn't matter, he still got hard every time he taped the breast forms to his chest and put a bra on.

As the months went by he ordered more and more from Lane Bryant. They had a 50% off sale. He ordered 3 dresses, a pair of dark skinny jeans and a pair of white skinny jeans, a couple of camis, two sheer rayon blouses, and a black pencil skirt. His closet was filling up with women's clothes. He wasn't confident enough to wear anything out of the house, but when he would come home from work he'd change into one of his new outfits for the rest of the night.

He let his hair grow long and bought a curling iron for putting a wave into it when he dressed up at night. He went to an electrolysis center and had his chest hair and beard removed. He started painting his toenails. He figured out he was a women's size 11 shoe and ordered some flats, a pair of 1-inch heels, and sandals from Lane Bryant. He bought PJs to sleep in at night, and a merry widow and a satin chemise for nights he was feeling especially sexy.

People at work noticed the gradual transformation over the first year - the long hair and the thinning of his beard. Nobody really cared or said anything. Over the first year he got to know the company's VP of HR well, both because she was part of the same executive team as his boss, and also because he usually saw her at least once a day in the smoking shelter.

Barbara Ann Kraft was the head of HR. She was a woman from a different era. In a workplace that skewed casual, she was dressed and made up every day. She was in her late 40s and there wasn't an ounce of fat on her. Every day she wore a sheer blouse with a bra in a complementing shade barely peeking out underneath. Her breasts couldn't have been more than a 32A, but David found something about Barbara Ann's look sexy. Monday through Thursday she always had a below the knee straight skirt that paired perfectly with the blouse, and on Fridays she'd go casual with a pair a gaberdine trousers. She wore nude hose every day, and always had at least a 3-inch heel.

The first time Barbara Ann saw David at the smoking shelter she ribbed him about his cigarettes - Benson & Hedges Full Flavor 100s. It was the same brand she smoked, and she joked you had to be a 45 year-old woman for a clerk to sell them to you. But it's what David had started smoking as a sophomore in college, he loved the flavor and the nicotine hit, and who cares if it was an all white 100. It forged a bond - Barbara Ann always went to the smoking shelter with just a single cigarette and her lighter. But if it was a tough day and David was there she always knew she could go to him for a second, or a third.

David's wardrobe grew, but he was still frustrated with his boobs. He'd put on a low cut top that fit perfectly, but there'd be no cleavage when there was supposed to be. He searched the internet for tips. The one tip he kept finding was that every girl needs a proper bra fitting at least once in her life. David had guessed at his size, and obviously he was wrong. He read that the clerks at Lane Bryant/Cacique would do a bra fitting, but he always bought online.

By August of 2010 he had built up quite a wardrobe, his face was smooth, his hair was long and wavy, and he had figured out the basics of lipstick and rouge. Mascara and eye shadow remained a mystery to him. He decided it was time to go out. He was going to get a bra fitting. There was a Lane Bryant store in a strip mall about 5 miles from him. He was afraid to cause a freak out in the store if he went for a bra fitting and they saw his flat chest and fake boobs, but he read that if you called in advance and arranged a fitting during a quiet time in the store, most clerks were pretty cool.

He called the Lane Bryant on Tuesday night and explained the situation. The clerk he spoke to was named Marcy. She sounded older but was completely unfazed by David's request. She told him Thursday mornings were always dead and she was scheduled this week. He should come in and ask for her. She told him he should wear his most comfortable bra and his breast forms and she would do the rest.

12