Giving It Up

Every guy worries about finding the right girl. Even though I was 18 years old and in my senior year of high school, just a week away from graduation, I still had anxiety when it came to girls and dating. Being a tad on the social awkward side, I was never very good with the female species. After several failed flings, I met Amber who was the same age as me. She was amazing, blonde and pretty, perky and cute, with a great body. Even though we had only been dating for three months, I knew that she was the one for me and I knew that I'd do just about anything to keep her.

Amber definitely wielded the power in our relationship and, being immature and insecure, I pretty much did whatever she wanted. I catered to her every wish, driving her places, buying her things, and being on call for her 24/7. I was pretty much her lap dog. Not that I minded much. I was just happy to have someone as beautiful as Amber in my life and I never wanted it to end.

Amber and I spent almost all of our free time together. I lived with my dad and he usually didn't get home from work until late, so we pretty much had the house to ourselves. This, of course, gave us plenty of opportunities to explore and experiment sexually.

One Friday night we were sitting on the couch watching TV. We had smoked some pot earlier and were feeling pretty buzzed.

Amber looked over at me and said, "I really like you, Dylan."

"I really like you too, Amber," I replied not knowing why she was acting so sentimental.

"And you would do anything for me?"

"Of course, babe, what's this all about?"

"I don't want you to freak out, but I kinda want to take our relationship to the next level."

"What do you mean?"

"Well, I'm going to ask you to do something for me, and it's kinda weird, but it's something I've been fantasizing about for a long time."

"You know I'd do anything for you, babe, just tell me." I was starting to get nervous and curious at the same time.

"What do you think about doing it with another guy?"

"Like a threesome?"

"Like you dressing up like a slutty girl and giving a guy a blowjob and letting him fuck you in the ass while I watch."

"Um...," I struggled to find words.

I was absolutely shocked by Amber's request. The thought of dressing up like a girl and doing things with another guy disgusted me at first. It felt pretty weird for a boyfriend to hear his girlfriend ask him to make love to another guy just so she could watch, but I couldn't help feeling a certain thrill from the sheer curiosity of it.

"Um, this is really weird, babe," I said. "Are you sure this isn't just the pot talking?"

"No, I really want this," she said in a serious tone. "Ever since I can remember I've wanted to see a guy getting fucked by another guy up close in person. It would be so kinky for me," she said seductively placing her hand against the front of my pants, "seeing you dressed up like a slut, in a submissive role, getting dominated by some hot stud. God, I'm getting wet just thinking about it. Could we please do it tonight? I really, really need this, Dylan."

"Um, well, I...I guess we could," I reluctantly consented. I was worried that if I refused she would leave me for someone who was more open to experimentation. "Did you, uh, have someone in mind?"

Amber averted her gaze for a while as if she was thinking about something. When she returned her eyes to mine her mouth contorted into a devious smile. I could tell she had an idea brewing in that pretty head of hers.

"You know, babe, I've got a naughty idea," she smirked. "It would be really hard to find someone on such short notice, but we both know someone who will be home shortly who could...you know...fill the role."

"Amber! You don't mean...," I was completely shocked that she would even think that that would be an option.

"Sure, why not?" she replied nonchalantly. "Seeing you do it with your dad would make it like ten times hotter for me. He's not just some random guy, but someone you love and respect. It's like super dirty and super romantic at the same time. Plus, your dads like mega hot. I bet his cock is totally gorgeous!"

"Amber! You can't be serious!" I protested in disgust. "He's my dad! That's so gross!"

"So you think my fantasies are gross?" she said in a bitchy tone. "Maybe I should just go then. I was so stupid to think..."

"Amber, wait." My greatest fear was now being realized. If I didn't give into her demands and go through with this, then she would find someone who would. This was her way of giving me an ultimatum. "Please, I just..."

"Look, Dylan, I know putting you in an awkward position," she said returning her hand to my crotch. "But, if you think about it, what I'm asking you to do isn't all that weird. I mean, you love your dad, right?"

"Of course I do."

"Well, wouldn't the best way to show your dad how much you love him be to satisfy his sexual needs?"

"I...um..."

"Think about it, Dylan, he's forty-five and divorced, he doesn't get out much and probably hasn't gotten lucky in a while, what with his stressful job and everything. Think about how happy it would make him to release all that sexual tension."

"I...I don't know, babe," I stuttered.

"Don't tell me you've never thought about what it would be like to, you know, be with a man your dad's age, on your knees, taking his cock down your throat, begging for him to fuck you. It would feel so wrong and so right at the same time, a teenage boy doing it with an older guy. I know you're thinking about it; I can feel your dick getting harder by the second."

She had me. I couldn't deny that I was getting hard thinking about how kinky it would be doing it with my dad. I know, it probably sounds strange, but I was high and horny and Amber had slowly talked me into it. I was curious. A few years ago I had stumbled upon a bunch of raunchy father/son sex stories online where the son dressed up all feminine and seduced his dad. Reading these stories had gotten me super hard, so when Amber suggested bringing out my girly submissive side and doing it with my dad no less, I guess I couldn't deny it made me even more open to the idea.

"I'll do it," I said flatly.

"Oh, thank you so much, babe!" she hooted giving me a big hug. "You have no idea how much this means to me."

Amber's excitement made it clear to me that she cared little for my own personal feelings. I was nothing more than a pawn in making her sexual fantasy a reality. But I didn't want to lose her so I played along.

My dad was going to be home in an hour, so Amber put me to work getting ready. She grabbed her backpack and led me upstairs to the bathroom. We took a shower together and she shaved my body smooth. She made sure my asshole was clean by sliding a soapy finger in and out. It felt weird, having something in my ass, but it didn't hurt and after awhile it felt kind of good. It helped that Amber played with my dick and balls to ease some of the tension I was feeling. She gave me a sensual kiss and told me how happy I was making her, which made me feel a little better about the situation.

After we finished showering Amber toyed with my bleached blonde emo-ish hair, giving me a sexy comb over to make me look more fem, and put some eye shadow and pink lip gloss on me. Next, we went to my bedroom. She dumped the contents of her backpack onto my bed to reveal a colorful assortment of thongs, panties, bras, stockings, skirts, dresses, blouses, heels, and all manner of lingerie. I was taken aback. She had clearly been planning this for some time. I had never thought about wearing women's clothing, but the thought of doing it wasn't a total turn off.

Amber picked out a black mini-dress and held it up to me.

"Here," she said handing me the flimsy garment. "We're practically the same size, so this should fit you."

She grabbed a black g-string with a cheetah print on the front, a string of fake pearls, and a pair of chunky black six-inch platform heels and gave them to me.

"Amber, what if my dad doesn't go for this?" I asked holding the outfit out in front of me.

"He will, trust me," she answered. "I read online somewhere that all dads have sexual fantasies about their sons every now and then, it's like natural, a taboo or something. Anyway, they see them as girls, so the more feminine we make you look the more he'll want you. But for this to work you need to make your dad believe you want him too. I'll try to help you as much as I can, but you're the one who needs to convince him."

"But how?"

"You'll have to flirt with him, talk dirty to him, and urge him on. If you show him how willing you are, he won't be able to resist you. Trust me, I know guys."

"I...I'll try to do my best," I said.

"You'll do fine, sweetie," she said. "Oh, I almost forgot."

She reached into the front pocket of her backpack and pulled out a tube of KY lube and a small pink butt plug.

"Uh, what is that?" I asked nervously.

"It's a butt plug, Dylan, duh," Amber said. "We need to make sure your asshole is nice and ready. Now, bend over."

I put my hands on the edge of the bed and did as she commanded. I heard her squirt some lube on the toy before feeling the cold wet tip press against my asshole.

"Unh," I grunted as she slowly began inserting the plug past my sphincter.

I felt a little bit of pain radiate through my anal walls. My body reacted by trying to push the intrusive object out but Amber held it firmly in place. Honestly, it didn't really hurt all that much; it just felt weird and uncomfortable. I had never had anything up my ass before, so this was an entirely new experience.

"Almost done," she said after it was almost all the way in. "You're doing great, baby."

When the last few centimeters slid in, I was left with a feeling of complete fullness in my asshole. It sorta felt like I had to take a big shit.

"There, how does it feel, babe?" Amber asked.

"Uh, kinda weird, but not that bad," I said.

"Great, get changed and I'll meet you downstairs," she said. "I'm so excited. I can hardly wait."

She gave me a peck on the cheek and left me to change alone in my bedroom.

I stripped off my t-shirt and jeans and began the process of transforming myself into a sissy slut. I took the mini-dress and tossed it over my head, allowing it to fall to the top of my thighs. It fit tight around my chest and stomach and barely covered my ass cheeks. Next, I slid the thong up my smooth milky thighs until it stretched between my butt crack. I sat down on the edge of my bed and put on the chunky black heels. To top it all off, I double wrapped the long pearl necklace and slipped it over my head, allowing the creamy white orbs to dangle against my exposed neck and chest.

I spent a few minutes staring at myself in the mirror. I didn't look half bad. In fact, I looked pretty damn good! The sexy outfit highlighted my more feminine features like my tight belly, bubble butt, and long legs. The contrast between the black dress and my pale white skin was a real turn on. I noticed a bulge forming in the front of the dress near my crotch. Honestly, I was getting incredibly horny just looking at myself. The butt plug lodged in my ass didn't help matters. If I could, I would have bent me over right then and there and fucked the shit out of me!

"Wow, babe, you look incredible," Amber said as I stumbled in the heels down the stairs into the living room.

She was still wearing the clothes she had on before: a white tank top, skimpy jean shorts, and black converse sneakers. She walked over to me and immediately started running her hands all over my body, feeling my chest, belly, and ass through the soft material of the dress.

"Oh my god, look at you," she giggled. "Your dad's totally gonna love it."

I felt a lump forming in my throat at the thought of having to confront my father dressed like a hooker.

"God, your ass looks great in this," she said turning me around so she could see my backside. "I'm so turned on right now."

"Really?"

"Totally, my pussy is dripping wet," she purred. "I can't wait for your dad to get home. This is going to be amazing."

As with everything we did, I let Amber take the lead, allowing her to lead me by the hand over to the couch. We sat down, our legs touching, her hand gently caressing my exposed thigh.

"You know, Dylan, I've always thought you were kinda girly," Amber said gazing deep into my eyes. "I think you look so hot right now. Any guy would be lucky to get the chance to fuck you."

"Uh, thanks, I guess." I didn't really know how to respond to a compliment like that. "I'm just so nervous, if this ever gets out..."

"Don't worry, I won't tell anyone," she said in a soothing voice. "Just relax."

She brought her small hand to my chin and turned my face toward hers. She leaned in and planted a tender kiss against my lips. Her lips felt so soft and gentle. I responded by wrapping my arm around her back and pulling her into me, hungrily mashing my lips against hers. Our mouths opened wider and wider, allowing us to swap spit between us. It was intoxicating, the feeling of the stud in her tongue rolling over my own slick tongue. My body relaxed and responded to Amber's touch as I allowed her tongue to explore my warm wet mouth.

As we continued making out, her hand slowly moved up my thigh and under the hem of the dress. I felt her grab and squeeze my ass cheek. Something about her touching me like that, treating me like I was a girl, started getting me really excited and I felt my already hard boner stiffen a little more. My hands began exploring her body, groping her ass through her shorts. It didn't feel like our normal make out sessions. It felt different, almost like I was a teenage girl making out with another teenage girl.

We got so lost in the moment that we failed to hear my father come in through the front door.

"Dylan? What the hell?!" I heard my dad gasp. His briefcase made a loud "clunk" when it hit the floor.

Amber and I abruptly broke our kiss and turned to him. He was just standing there, in the doorway, with his mouth hanging wide open.

I'm not going to lie. My dad looked amazing for a man nearing fifty. Tall, tan, and muscular, he was a pillar of confidence and masculinity. He went the gym often and kept his body in shape. He often reminded me of a Men's Health model, clean-shaven, dark hair with grey speckled in, and absolutely handsome. We had a really good relationship. Having lived alone together for almost twelve years without my mom, we did a lot of "guy" stuff together like going to sporting events, playing video games, watching Star Wars (our favorite movies), and occasionally drinking beer together even though I was still underage.

When he walked in on us a wave of shame and embarrassment washed over me. I started to get really nervous, my body shaking all over, my cheeks flushed. I had gotten so lost in making out with Amber that I had completely forgotten that the major part of her fantasy involved me doing the nasty with my own dad. It finally dawned on me that her twisted fantasy could ruin the very healthy relationship I had with my father. I started to get scared that the man I loved so much, the only family I really had, might actually disown me.

"Follow my lead," Amber whispered into my ear.

I gulped.

"Hello, Mr. Johnson," she said in a cute perky voice.

"Dylan, what's going on here?" my dad asked sternly.

"Dylan has something he needs to tell you," Amber said turning her attention to me. "Go ahead, babe."

"Dylan?" my dad asked with a concerned look.

This was my moment.

"I'm sorry, dad," I said dropping my head before raising it again to meet his puzzled gaze. "But I think I have a crush on you."

He just stared at me with bug eyes for a few seconds before uttering, "I, uh, I don't understand."

The look of shock and disgust on his face started to make me think that Amber's plan wasn't going to work, but her words came back to me: "You'll have to flirt with him, talk dirty to him, and urge him on. If you show him how willing you are, he won't be able to resist you."

"I just...I just can't stop thinking about you," I continued trying to summon as much confidence as I could. "I can't stop...thinking about all the things I want to do to you...and all the things I want you to do to me."

I couldn't believe I was actually saying these words out loud. But the more I did, the more I gradually started to believe them.

"Holy shit, Dylan," my dad said with a deep sigh running his hands nervously through his hair. "I, uh, I just don't know what to say."

"Come on, babe," Amber said taking my hand.

Together, our hands entwined, we walked over to my stunned motionless father. I was so nervous. Each click of my heels against the wood floor seemed like a nail being driven into my coffin. We didn't stop until we were practically touching him.

"Doesn't your son look sexy, Mr. Johnson," Amber said. "He wore this outfit just for you, and he's willing to do anything you want...anything."

"But Dylan, I don't...," my dad said struggling to understand the situation. "What is Amber doing here?"

"Oh, don't mind me, Mr. Johnson," Amber replied. "This was all Dylan's idea. He loves you so much and wants to make you happy. I'm just here for moral support."

"Dylan, I can't...," he said, sounding a little irritated. "You can't...you can't feel this way...it's wrong."

"Your cock doesn't lie, Mr. Johnson," Amber teased running her hand along the unmistakable bulge forming in the front of my dad's dress pants. "From how hard you are, I can tell how much you love seeing your son dressed up like a cheap whore."

She wasn't wrong. Even though he still had his pants on, I could clearly see my dad's cock stiffening up by the second right in front of me. His face looked so flustered, like he was angry and horny at the same time. It kind of made me feel a sense of pride and accomplishment knowing that I could have that effect on an older guy, my own father no less. I wanted to explore it more. Slowly but surely, Amber's perverse fantasy was becoming my own.

"No, I, uh," my dad said pushing her hand away. "It's just that...what if..."

"Don't worry, Mr. Johnson, this is just between the three of us," Amber winked at him. She took my hand and pressed it against the front of my dad's dress pants. "Here, babe, feel how hard he is for you."

As soon as my hand reached his pants, I immediately felt the rigged outline of his cock pulsating against my palm.

"Oh, wow," I said softly, mesmerized by the fact that I was feeling up my own father.

I couldn't believe I was actually going through with this. A little over an hour ago I was just a normal straight high school senior with an overbearing girlfriend. Now I was touching my dad in a sexual way. It should have felt wrong, but it didn't. In a lot of ways it felt completely natural.

With her hand still on top of mine, Amber encouraged me to take it one step further, moving my hand up and down his crotch.

"Oh...Dylan...," my father moaned.

I could tell he was enjoying it. His eyes rolled into the back of his head as my hand slowly ran up and down the full length of his sheathed cock at Amber's urgings. Before long she let go and my hand moved on its own. Sensing an opportunity, Amber nudged my arm with her elbow, and mouthed, "Flirt with him," to me, before stepping away from us.

"Oh, daddy," I purred in the most innocent girly voice I could muster. "Your cock feels so hard."

"Dylan...this is so wrong," he groaned in protest. His body was responding to my touch, but his mind was still trying to resist me. "If you weren't my son, I'd want you, but..."

I ignored his pleas and continued massaging his clothed shaft. The more he resisted me, the more I wanted him. I couldn't remember ever wanting anything more. For eighteen years I had loved him as much as a son could, but now I wanted something more, something deeper. After all the sacrifices he made for me over the years, I wanted to pay him back, give him the pleasure I knew he was missing out on. I knew the best way to make him completely give in was to show him just how much I wanted this.