Friends with Benefits

Story Info
When Eric befriends Dave, the sissy in him comes out.
5k words
4.62
56.4k
51
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

It was late Saturday evening when Dave and Eric, shuffled home to Dave's place. They were returning from a party at the campus pub and were slightly inebriated. Eric had never fit in with the popular, party-going crowd in high school, but now hoped it was different in university.

Dave had a nice apartment off campus, and Eric enjoyed the freedom of hanging out with his new friend away from his mother's prying eyes.

They met in their sociology class, and became friends when paired up together on a project. David had an engaging manner that allowed Eric to take the lead on the project. Another way of expressing it would be that David left Eric to do all the work. Eric barely noticed as he was used to being taken advantage of.

He was ecstatic when David invited him to this party. Being part of a group would be a new experience, and he would be going with a tall, well-built, masculine guy; exactly the time which bullied him in high school.

He still didn't quite fit in, and clung to David's side most of the night. He couldn't hold his liquor very well, and was drunk after a few beers.

David seemed unimpressed with the party for his own reasons. Eric couldn't fathom what bothered David as he seemed to be welcomed into this social clique. However, he readily agreed to leave with him and was excited to visit David's place. It must be so wonderful to have your own space.

They settled into the rec room, and flipped through the late night TV offering. The only thing they came across of any interest was a blue movie. This rather shocked Eric as he could never watch adult films with his mom and sister around.

David had the opposite reaction. "This is pretty tame, kind of like those stuck up bitches tonight."

"What do you mean?" Sensing he was now going to learn why David was bored at the party, his curiosity was piqued.

"Those girls... Oh excuse me, young ladies," he said sarcastically, "... They hardly give you the time of day. Either that or they are obvious gold diggers. Not one of them will put out."

Eric nodded in agreement, when in reality he had no idea what David was talking about. Girls had always treated him with disdain; the nerdy kid no girl would hang out with. Eric seriously doubted that David suffered the same affliction.

"How open minded are you?"

Eric wasn't certain how to answer. He was fairly liberal minded, but still being a virgin, he didn't have the life experiences to know for sure.

"I guess I'm fairly open minded."

"If I put on something really freaky, do you promise not to tell anyone."

Now this was getting really intriguing. "I promise."

David went to his bedroom and returned with a collection of DVDs. They were obviously copies as there were no cases or labels on the discs.

The video appeared to be your standard porno, with a ridiculous plot, a buxom brunette in a revealing outfit, and a muscular guy already sweating from his work.

Eric had accessed some videos like this on his computer when his mom wasn't around. Yet it still felt weird to be watching them with another guy. David was really starting to get into it. He had unbuttoned his fly and was rubbing the bulge in his underwear.

Eric tried not to look at David, and was uncertain how he should react.

The woman on the screen was now topless and the man was sucking her nipples. Her hand gripped the man's cock and stroked him furiously. Exactly on cue, and quite predictably, the woman knelt down and began sucking him off.

David was really starting to get into it. He now had his dick in his hand, and was slowly jerking himself off.

Eric was really getting freaked out. He debated saying something. Yet at the same time, he couldn't help looking at him. David's cock was huge; as big as the one on screen. Eric had no compunction to pull out his cock, and was now more reluctant considering how small his cock was in comparison to David"s.

On screen, things suddenly took a twist. The guy pulled down the woman's panties as they kissed. Yet as the camera panned down with the man's hand reaching between her legs, he did not stroke her pussy. Instead, he grabbed her cock.

Eric sat forward; stunned. He had watched some tranny porn on his computer, actually quite a bit really. However, he had never expected a hunk like David to like shemales.

David had a wide grin on his face as he observed Eric's reaction. His cock was firm, and still being stroked furiously.

The tranny on the screen was bent over, and the man positioned himself behind her spread out legs. He then slowly penetrated her ass, and began fucking her hard and deep. The tranny gasped with each thrust.

David was sitting back, knees spread, and jerking hard on his cock. Eric even spotted some pre cum on the tip of his penis, and unconsciously licked his lips. His own cock was now hard and strained against his pants.

Eric wasn't certain what was coming over him. Perhaps it was the alcohol, or his favorite type of adult video with a hot tranny, or just the bizarre situation with David jerking off beside him, but he was getting really horny. Not just horny, but turned on by David and his huge cock.

He couldn't tell what compelled him to do this, but he knelt down and began to suck David off. David ran his hands through Eric's hair and just enjoyed the moment. Eric was really getting into it, imagining all those videos and photos of trannies and crossdressers devouring a throbbing cock. He loved the hardness with the smooth touch which penetrated deep into the throat.

He could hear the man on screen grunting with his own orgasm. David was not far behind. Eric tasted the first bit of salty goodness, and began to suck even harder. David gripped his hair.

"Oh yeahh!! Take it bitch."

David shot his load deep into Eric's throat, and Eric didn't miss a drop.

Exhausted and drunk, David passed out on the sofa with his pants open and Eric kneeling before him.

Eric rose with a blush of embarrassment which no one saw. He looked down at David and his now softening penis. Part of him wanted to be mad at David for setting up this scenario. The other part of him knew he had not been forced, and could forgive this gorgeous man anything.

He looked back at the TV where a new tranny was being fucked on the bed. He slipped quietly out the door, wondering if this was how they began.

Chapter 2

Eric's sister Claire noticed something was up right away.

"What's up with you? You've been acting strange since Friday night."

"You know me, I can't hold my liquor, and I got a little drunk."

"That's for sure, most of my girlfriends could drink you under the table. But even a sissy like you can't be hungover the following day."

Eric was startled by Claire calling him a sissy. He shouldn't have been surprised as she always called him that. His sister noted his reaction, particularly the lack of his usual denial. Sensing she was onto something juicy, she pestered him further.

"Why aren't you returning your friend David's calls."

"Why do you care?"

"Ohhh touchy, touchy. Lovers quarrel?" She said with a laugh.

"No!". He looked away as he said it. "He's just a study partner, and a new friend. Do you think I'm not able to make friends?"

Eric was completely over reacting to her teasing, which made it apparent something had happened. She was tempted to torment him further, but it seemed that now was the time to be his protective older sister. She sat down on the sofa next to him, and hugged him.

"What happened?"

He was caught off guard by her sudden gentleness. She hadn't been this nice since the years she fended off bullies at school.

"Sis, am I really a sissy?'

"Oh honey, did David pick on you."

He stared at the ground and shook his head. "No, it wasn't like that". He spoke so quietly she could barely hear him.

"I know I always tease you, but you are my brother, and I love you. You can tell me anything sweetie."

"Well David and I went back to his place after the party. We were both a little drunk, so I don't know how much he remembers". Claire was listening intently, rubbing his shoulder reassuringly.

"... Anyways, he put on this porn flick. But it wasn't a typical porn flick.". He was starting to sound defensive. "It was a shemale flick"

She nodded.

"And I got horny. Well, we both got horny. Then I sucked him off. I mean, he didn't even ask me to I just did it."

He started to cry. "I guess that makes me a sissy now."

"Sweetie, you have been a sissy since you started stealing my clothes."

Eric sat up straight and stared at his sister. "What?!"

"Oh please, I've known for years."

He looked down in embarrassment. "So you think this was inevitable."

"I have imagined making you over so many times. It always makes me excited."

"And why should I get made over now?"

"David wants to see you again, and we both know what turns him on. And we both know what you have been fantasizing about for years."

"Yeah, but those shemales were hot".

"O yea of little faith," she chided. "I'll make sure David gets a hot girlfriend."

She curled her finger through Eric's hair and smiled at him.

He was starting to buy into all this. Claire smiled, delighting in how easy it was to manipulate him.

* * *

Eric avoided David until the next day at class. It was in the lecture hall where he could have avoided him further, but instead waited behind after class.

David walked over to him. "I'm sorry I freaked you out the other night. I was phoning to apologize."

Eric smiled, consciously appreciating for the first time how nice and attractive David was.

"I'm sorry for not returning your calls. I've never done anything like that before. I guess I was a little freaked out."

"Let's forget it ever happened". David tried to reassure him.

"Was I that forgettable?". Eric teased him.

David chuckled, startled by Eric's sudden eagerness. "Not at all". And then whispering, "actually it was the best blow job I've ever had."

"Beginner's luck."

"Beginner?"

Eric smiled in response. "Are you free on Saturday night?"

David shuffled in his seat, visibly uncomfortable.

"For a moment I thought you had done this before," Eric stated in a half questioning manner.

"No, not really. I mean... well there was one kid back in high school. We didn't date. I just made him suck me off a few times. But people never knew. I'd have beaten the shit out of him if he told anybody."

David evidently was just like the bullies which used to taunt and beat up Eric in high school, only he had a secret.

"So you are worried about people seeing us together."

"Yeah, if I'm going out on a date, or to some party, its going to be with some hot babe. Sorry, but that's just the way it is."

Eric nodded, "Don't worry about it. And hey, maybe we could hang out like regular guys."

"Yeah sure, but you better not say a word". The implied threat was obvious. Then he lightened up. "What happens if the chick doesn't put out, like Friday night?"

A few short days ago Eric would have been terrified of the implication. Now, he was excited. His only response was a wink.

Chapter 3

David didn't have any plans for Saturday evening, and the two of them planned to go to a club Saturday together.

Claire was almost as excited as Eric when she heard about it. "Now is your chance."

"What?! We're just hanging out."

"You're just hanging out until David finds a hot girl. I think you should be that hot girl."

"David isn't going out with a sissy. I told you, he's still in the closet, and he'd beat the shit out of me if I outted him."

"Give me the day to feminize you. If you don't think you're beautiful at the end, just phone David and tell him you're feeling sick."

"And why should I let you make me over, even if you could do a good job?"

"Because if you don't, you are going to spend the evening pinning after him in the corner of the club while he hits on every available girl in sight."

She was right, no matter how much Eric wished that she wasn't. "What if someone finds out?"

"Who? Mom's on her business trip, so we have the place to ourselves for the day. And I promise you'll be ready before David picks you up."

Eric stood up and paced a bit. "OK, but no tricks. If I don't pass as a woman, I'm not walking out this door."

"Agreed". She took his hand and lead him to the bathroom.

"Now, run a bath". Handing him a razor, "... And shave all of your body hair. All of it!"

As Eric sat in the bath, alone with the razor in hand, he began to have second thoughts. Yet the other part of him felt there was nothing to lose. He had spent so much time over the years wearing the clothes he stole from his sister. Now it was time to find out if he could really pull it off.

His sister was always hot looking, and he had envied her popularity. If anyone could help him look sexy, it was her. He began shaving.

He was just finishing when his sister walked back in.

"Hey" he cried out and attempted to cover himself.

She laughed, "Don't be silly, you've got nothing worth looking at."

In humiliation he dropped his hands and finished up in the bath tub.

She tossed him a tub of cream. "Here, put some of this on. It will relieve any itchiness from shaving and make your skin smoother."

He noticed the flower scent immediately, but proceeded as instructed. As promised, it did make his skin feel soft. He idly stroked his legs, delighting in their silky feeling.

Claire giggled at him. "I should have forced you to do this years ago."

"Ok, put these on". She tossed him a matching bra and panties.

He put them on, feeling silly, but he had done this many times before. The bra had some padding which gave him some breasts.

He was then led to her bedroom, and seated before her mirror.

"I am so glad I talked you out of cutting your hair. Now you don't need a wig".

She combed his hair out, trimmed it in a few spots, added some extensions, and then began styling it. Eric sat patiently, trusting her judgement.

Eric's only complaint was a lack of clothes. She dismissed this by simply saying, "No, I like you better this way."

Claire was clearly loving this whole exercise. It was also clear from the way she quickly moved the process along that she had given this a lot of thought.

Eric tried to resist having his ears pierced, as this would be permanent, but this too was easily dismissed. "Don't be silly, lots of guys wear ear studs."

Next came his eyes lashes, which were tweezed, and sharpened with eyeliner. It was really coming together. Eric was amazed by his reflection. Once earrings, some rouge, and lipstick was applied, the effect was complete. With each step, he - or was it now she - was looking more and more gorgeous; and his resistance diminished.

Next came the false nails, which were then painted scarlet red. The toe nails were painted to match.

Hours had passed since they had started, but they were both still having fun. They were even beginning to joke and gossip amongst themselves in a way they had never done before. It was becoming the slumber party they had never had.

"Ok Erica, I bought a dress that I think is perfect for you."

"Erica??"

Claire pointed to the reflection in the mirror. "Yes Erica.". Looking back was a lovely woman with wavy brown hair, smooth skin, a thin graceful body, long sexy legs, and beautiful blue eyes.

"Ok, Erica it is." Looking back at the reflection, he wondered out loud, "Do you think David will like me."

Claire hugged him/her. "Sweetie, he's going to love you."

The dress was indeed perfect; black with red flowers, knee high skirt, and a long neckline. "Oh sis, it's wonderful!" Erica squealed with delight.

"Ok, ok. Don't get ahead of yourself," Claire chided, but was secretly delighted in the reaction. "You need to put your stockings on first."

It was revealing that he put them on with ease, even getting the seam right. As Erica was putting on the dress, Claire pulled out a pair of open toed, high heeled shoes.

The shoes fit perfectly. Claire shook her head in disbelief. "Given how much you match my size for dresses and shoes, I can't help but wonder how many of my clothes you have worn without me knowing."

His silence and sheepish grin spoke volumes. She shook her head, partly out of disgust that her things had been used so brazingly, and partly out of amusement at her sissy brother. "From now on, come to me, and I will help you buy your own clothes and makeup."

"I promise." He was really enjoying the look and feel of this dress, and felt certain he would be doing this again.

Erica wobbled in the heels initially, but quickly got the hang of it with some tutoring from her sister.

"When is David supposed to come by, or are you meeting him somewhere?"

Suddenly, Eric had a lump in his throat. He had forgotten that all of this was for him, and David had no idea about any of this. Eric had never expected this would work, but now that he was a sexy looking woman, he was not certain how David would react.

Claire could tell how nervous he was. "Since you're going out to a club, I suggest you ask him to pick you up here around 9."

Eric nodded.

"Well go on, make the call."

Eric slipped into his bedroom for his cell and called David. Returning to his sister's bedroom, he informed her, "David's going to pick me up around 9:30. I told him I have a surprise for him."

"Great that gives us lots of time to practice you're walking, and maybe some dancing. And we'll also need to work on your feminine voice. Let's have something to eat first."

They proceeded downstairs to the kitchen, being extra careful walking down the stairs, and made dinner. They chatted throughout, stopping and correcting Erica's tone periodically. Later they did some touch ups on his hair and makeup. By 9:25 when the doorbell rang, Erica was as ready as she would ever be.

Chapter 4

Claire welcomed David in, and exchanged introductions as they walked to the living room. She called out from the bottom of the stairs, "Erica, David's here!"

David paused for a moment and then shook his head, figuring he just misheard. He sat on the sofa and waited.

Eric's other sister came down the stairs and into the living room. "Hi David, what do you think?" She did a slight turn and pose.

He looked at her like she was crazy. She was smiling at him as if she knew him. He looked at her more closely.

"Holy shit!"

Erica stood nervously before him, praying that he would not walk out the door. "Surprise," she said softly with a shy grin.

Claire walked to Erica's side and put her arm around her. "Doesn't she look great."

David nodded, "yes, SHE does."

"I told you I had a surprise for you," Erica said. His soft feminine voice was very alluring.

"Yes, yes you did, but... Holy Shit." He really didn't know what to think. He was completely ambushed. However, he couldn't deny that 'Erica' looked hot. He was getting aroused staring at 'her'.

She stood before him, shifting nervously in her heels nervously, as he looked over her body. At least he wasn't pissed, or walking out the door, which had to be a good sign.

"OK, fuck it. I didn't recognize you, so who will at a night club where no one knows us." He stood up and kissed her.

Erica squealed with delight and hugged him. Even wearing heels, she had to look up to him. She then gave him a long passionate kiss.

Flushed, he took Erica's hand. "OK sweetheart, let's see how you move on the dance floor. I'm sure your sister didn't dress you up to be a wallflower."

"Have fun." Kate wished them as they exited the door.

When they got to the club, Erica started to get nervous, and could see David was also on edge. A couple of drinks later, they started to relax. That's when Erica coaxed David onto the dance floor. She was now grateful for the practice her sister had given her earlier, as she was able to move gracefully. She swayed her hips, and was really getting into it. David held her close, and she rubbed her body against him.

12