Sal had had a rough day at work. A heavy box had fallen and broken his wrist.
After a long wait in the emergency room, he was finally on his way home. The
only good thing to come out of all this was that he was still going to be home
about an hour early. An hour he figured he’d spend with his roommate and best
friend, Eli.
Sal and Eli met in middle school. Eli was being bullied and Sal stuck up for the
smaller boy. From there, their friendship was set in stone. Eli did get bigger,
but not by much. He was still quite petite for a man and, in the right light,
one could even say he looked feminine.
None of this would reduce Sal’s shock at finding a woman in lingerie in his
living room.
“Oh, I’m so sorry, I didn’t know Eli would have anyone over-” he said, but
stopped mid sentence. The woman looked familiar, too familiar. “Wait… Eli?”
“Y-yeah.”
“You’re a crossdresser?”
“I… uh… y-yeah, I crossdress sometimes.”
“Oh… Am I the only one that knows?”
Sal doubted that Eli would tell anyone else. He didn’t have any other close
friends, nor did he have a girlfriend. Sal knew Eli’s parents and they were the
conservative type. They certainly wouldn’t approve of this. The same was true
of Eli’s boss.
“Yeah. Please don’t tell anyone!” begged Eli, walking closer to Sal.
He stared down at his friend’s lithe body. He knew what he wanted and he knew
exactly how to get it. It wouldn’t be right though… It would be an awful thing
to do… These thoughts ran through his head at he stared at his friend’s pink
lips.
“Get on your knees,” commanded Sal.
“What?”
“If you don’t want me to tell anyone, then… get on your knees.”
Eli dropped to his knees. “Please, I just…” Eli started, but stopped when Sal
pulled his dick out of pants shorts.
“Your pretty pink lips for my silence.”
“Pretty?”
“Suck it.”
Eli leaned forward and took the head in his mouth. It was his first time giving
a blowjob, so he did his best to emulate what he had seen in porn. He sucked the
tip while working the shaft with his hand.
Sal was in bliss. He hadn’t been with a woman in months and now he had a cute
girl on her knees sucking him off right in his living room. And best of all,
that girl was his best friend that he had complete dominance over now. The power
went to his head and made the amateur blowjob that much better. He pulled Eli’s
head down on his cock, unloading as far in as he could.
Eli choked as the sticky cum was unleashed into his mouth. He did his best to
swallow as much as he could, but still some ran down his mouth.
Sal, satisfied, pulled out of his friend’s mouth and looked down at her. Cum
ran from the corners of her mouth, her make up was ruined, and tears trailed
down her cheeks. Realization finally hit Sal, he had just raped his friend. He
quickly pushed past her and went into his room.
“What the fuck did I just do?” he asked himself. “Eli must hate me. Fuck, he
might call the police… I’d deserve it.”
Sal waited in his room, but the police never came. Eventually he got hungry and
left the room to make food. While Sal was making a sandwich, Eli sheepishly left
his room too.
“H-hey,” he said to Sal.
“Uh, hey.”
“Uhm, so, you’re not going to tell anybody… right?”
“No… No I won’t tell anyone.”
“Okay… thanks.”
Sal looked down in guilt. Eli had even thanked him.
“Hey, uh, you don’t have to hide your stuff anymore. If you want to be a girl,
you can do that here.” Sal figured the least he could do was make sure Eli knew
he could be himself… or herself when they were at home.
“Oh, thanks. I might do that.”
“No problem… And you looked good… You were cute as a girl.”
“R-really?”
“Yeah.”
The two returned to their rooms and the rest of their night was more or less
normal, with the exception that they didn’t talk much.
——————————————————————————–
The next day, Sal got up and went to work early, avoiding Eli. He returned home
to see that Eli was already there, but he wasn’t in the living room this time.
Sal closed the door behind him and went to his room, where he changed out of his
work clothes then returned to the living room.
Once again, Eli sheepishly left his room, this time wearing girl clothes. It was
a different outfit from yesterday, which told Sal that she must have had at
least a few.
“H-hey,” said Eli.
“Uh, hi,” said Sal, trying to avoid staring this time.
“I figured I’d take you up on your offer and dress cute again… How do I look?”
Sal took the question as an opportunity to look his friend over again, “You look
really cute. I like your makeup.”
“Oh, it’s not much.”
“Yeah, but that’s what make’s it cute. I like that kind of almost natural look.”
“Thanks,” she said, blushing.
“So, do you have a different name when you’re… like this?”
“I like to call myself Ellie.”
“Ellie?” Sal laughed, “That’s cute.”
Ellie came over and sat down on the couch casually. She sat at the opposite end
of the couch from Sal.
Sal’s thoughts once again went to his friend’s supple lips.
“Maybe she’s not mad? Maybe she doesn’t care about yesterday?” he thought.
“Doesn’t care? She was crying you piece of shit,” he chastised himself. “But
then, maybe she changed her mind. I mean, she is being awful nice. And she
doesn’t seem to mind being around me.” He fought himself mentally, but
ultimately it was his lower head that won out.
“So… I was just thinking,” he said.
“About what?”
“Well… I mean, I won’t tell anybody, but it would really help me stay quiet if
you were to, uh, help me out again.”
“Help you out?” she said, playing dumb.
“Like yesterday? You know, help me out on your knees?”
“I-if that would help…”
“It would.”
She got on her knees and he fished his cock out, presenting it to his
crossdressing best friend. Ellie took it in her mouth, rolling the head around
with her tongue.
Sal breathed heavily, “Ellie, you’re so good.”
She continued to lick his head as she grasped him with her hand and started
jerking him off too. He lasted much longer this time, but eventually he gave in,
spilling his seed in Ellie’s mouth.
“I’m cumming,” he warned.
This time she was ready and was able to swallow all of it without issue.
Sal looked down at his best friend, he wondered what she was thinking, but her
face revealed nothing. Confusion maybe? She went to the bathroom, then came
back, sitting on the couch with him again. The rest of their night was spent
like any other: hanging out, enjoying each other’s company, then going to bed.
——————————————————————————–
The next day, Sal came home, changed clothes, and sat down on the couch. When
Ellie came out, she didn’t sit next to him though, she dropped straight to her
knees and went to work. Once again Sal blew in her mouth and the two spent the
rest of the night normally.
And this is how their lives went on for almost a week. But one night, Sal grew
bolder, he wanted more.
Ellie was on her knees servicing him when Sal asked: “Have you ever played with
your ass?”
She hesitated, clearly thinking about whether or how to answer, but eventually
she did. “Sometimes I finger myself in the shower.”
“You like it? It feels good to play with your boy pussy?”
“Y-yeah.”
“Let’s go take a shower then.”
Ellie didn’t say anything, no agreement, but no protest either. She simply
followed Sal into the bathroom. Sal stripped and Ellie followed his lead,
revealing her flat chest and bubble butt.
“Fuck you have a nice ass,” said Sal, pawing a handful of Ellie’s round cheeks.
The two stepped into the shower and Sal turned the water on, adjusting it to his
preference.
“Show me,” he said.
Ellie turned around and bent over, showing off her round butt. She reached a
finger back and inserted it, wiggling it around inside. Eventually she pulled
her finger out and Sal quickly replaced it with one of his own, larger fingers.
Ellie moaned and tensed up, trapping Sal’s finger tip in her tight anus.
“Relax,” he said calmly.
She did, allowing his finger to slip inside her. She wiggled his finger around
like she had with her own. Sal decided to press a second finger in alongside the
first, but found the resistance too much. Ellie winced in pain from the
unwelcome intrusion. He grabbed the body wash off the shower’s shelf and squirted
it onto Ellie’s generous back side. He used a single finger to massage it
inside, before finally inserting the second finger successfully.
Sal pulled both fingers out and used some more of the body wash to jerk himself
off. He stepped forward and pressed the head of his cock against Ellie’s tight
hole. Ellie looked back in surprise, but turned around again as Sal pushed
inside her. She tensed up again, gripping his cock with her anal muscles. The
tight grip of her ass only brought Sal more pleasure.
“Relax,” he told her again and again she did.
He was able to push further inside, pressing his hips against her plump ass.
He pulled out slowly, leaving only the head inside, then pressed in once more.
He started pumping in and out of her ass, until he couldn’t hold out anymore.
He didn’t stop when he started cumming, he continued fucking her, using his own
cum as more lube alongside the body wash, until finally he was sated. He pulled
out and his cum ran down her legs. She collapsed to the shower’s floor.
Sal was once again overcome with guilt. He fled from the shower to his room
where he spent the rest of the night. He awoke the next morning to the smell of
breakfast cooking. Eli and now Ellie would always cook breakfast for them on the
weekend. Sal doubted there would be any for him today. He was surprised, then,
when there was a knock on his door.
“You up?” asked Ellie.
“Uh, yeah,” called back Sal.
“Breakfast is ready. You hungry?”
“Uh… yeah.”
Sal sat down at the table and began eating. He wasn’t eating much and Ellie took
notice.
“Is something wrong?” she asked.
“No, I’m fine,” he said.
“Well, you’re not eating much.”
Every word only served to fill Sal’s heart with guilt. He had been so cruel and
she remained his closest friend.
“I’m sorry,” Sal said, tears welling in his eyes.
“Sorry?”
“About everything. I shouldn’t have done any of that. I made you… I’m sorry.”
“You mean for blackmailing me? So you’re not going to do it anymore, right?”
“No.”
“And you won’t tell anybody?”
“I never would have.”
“Then… why?”
“I just… I just wanted you. I’m sorry.”
“That’s all it ever was? You just found me attractive?”
“Yeah. I wouldn’t have told anybody. I never wanted to.”
“And now you feel guilty?”
“I’ve felt guilty the whole time. That’s why I ran to my room that first time
and why I did the same thing last night. I felt like shit Ellie… I hurt you.
You’ve been so nice to me and I hurt you. I can’t take it anymore.”
“That’s why?”
“Yeah?” he said, still crying, but confused.
“So you weren’t… disgusted?”
“Disgusted?”
“Like you didn’t regret it?”
“Well, of course I regretted it.”
“But, only because it was blackmail… right? Not because of me?”
“No. You’re great… that’s part of why I feel like shit. I’m so sorry.”
Ellie sat and thought for a while.
“Well, since you feel so bad, let’s make things even.”
“Make things even?”
“You have dirt on me, so give me dirt on you.”
“I don’t really have anything like that…”
“You have one thing.”
“What’s that?”
“You raped me.”
“Oh…” Sal said in depressed realization.
Ellie took out her phone and opened a recording app. She placed the phone in
front of Sal and hit the record button.
“Give me a confession.”
“A confession?”
“Yeah. Just say what you did into the microphone.”
“All of it?”
“Yeah. Everything you made me do.”
“Well, uh, I found my friend, Eli, wearing girl’s clothes. And I… I
blackmailed him. I told him I’d tell other people if he didn’t give me a
blowjob. And then…”
Sal continued to recount their story, giving all the details he could remember
about the weeks of blackmail.
“Is that good enough?”
Ellie ended the recording and saved it, then put her phone away.
“Yeah, that’s good.”
She then dropped to her knees in front of Sal and reached for his cock.
“What are you doing?”
“Sucking you off.”
“You don’t have to do that.”
“I don’t *have* to, but I want to.”
“Really?”
“I hated you after the first time. I wondered how someone that called themself
my friend could do something so horrible to me. But, after a while… I started
thinking differently. You weren’t just abusing me for sexual gratification, you
were really attracted to me. You’d even compliment me: tell me I was sexy, that
I had a nice ass, that I was cute. It made me feel better about myself and I
started to enjoy when you’d use me. And it’s not like you ever hurt me or
anything…”
“I did slap your ass a few times.”
“Yeah, but I liked it.”
“Really?”
“Yeah… So you can do that again… next time we have sex.”
“So… you want to keep doing stuff?”
“Yeah. Honestly, I was more worried that you were disgusted by me than I was
about the blackmail.”
“Seriously?”
“Yeah… I guess that sounds kind of dumb.”
“Well, it’s a relief to me.”
Ellie resumed her blowjob, sucking Sal to completion right at their kitchen
table.
“So how was that?” asked Ellie.
“Great. And so much better when I don’t have to feel guilty about it.”
“Good. Now eat your breakfast. When you’re done, come join me in the shower.”
Sal scarfed down his food, barely stopping to chew, then entered the steamy
bathroom they shared. He stripped and stepped into the shower to see his
friend’s soapy, feminine form.
“That was quick,” said Ellie, “You remembered to chew, right?”
“Mostly.”
Sal’s hand moved to Ellie, exploring her soft, petite frame. He looked down into
her brown eyes, then surprised her with a kiss. He pulled away at her surprise.
“Was that okay?” he asked.
“Yes, I just… I didn’t expect it.”
“Sorry, you’re just so cute and we’ve never kissed and-”
Sal’s rambling was cut off by Ellie pressing her lips against his. Sal kissed
her back and soon his tongue was invading her mouth. His hands reached around
to grip her back side as they made out. Ellie’s cock stiffened against Sal’s
leg. The two separated and he looked down at her girl cock.
To Ellie’s great surprise, Sal dropped to his knees in the shower.
“Y-you don’t have to do that,” she assured him.
“But do you want me to?”
“Well… I’d like that, yeah…”
“Then I want to do it.”
Sal grasped her swollen shaft and led it to his mouth, opening wide to accept
it. He imitated the technique Ellie had used on him many times, using his hand
to massage her shaft, while his mouth pleased her head. In under a minute, Ellie
was exploding in Sal’s mouth, delivering salty fluid to his tongue. He happily
swallowed for her, as she had done for him, then stood back up.
“That really did it for you, huh?”
Her faced turned red, “well, it was my first blowjob.”
“Was it?”
“Yeah. I’ve never been with anyone else before. Just you.”
“Oh… That’s… I’m sorry Ellie.”
“It’s okay. We’re okay now.”
“I know… I just think it’s shitty that your first time was like that.”
“It was… but now you have the opportunity to make up for it. To treat me
properly.”
“I will. I promise I’ll never do anything like that again.”
“Well, it’s not like you’ll have to,” she said smiling.
“So…”
“So?…”
“I just… I just wanted to ask, are we… together?” asked Sal.
“Like boyfriend-girlfriend?”
“Yeah.”
“Is that what you *want* us to be?” she asked, anxiety in her voice.
“Yeah. I want you to be my girlfriend.”
She looked up and kissed him, just a quick peck on the lips.
“Then I’m your girlfriend.”
——————————————————————————–
All of my stories can be found on:
* [AO3](https://archiveofourown.org/users/Original_Chicken_210/works)
* [Reddit](https://www.reddit.com/user/Original-Chicken-210)
Source: reddit.com/r/eroticliterature/comments/snvgkl/guilty_pleasure_mmfemboyblackmailromance