Pegged for Love

It is probably the truest saying in the world: you can’t just be friends with a girl of the opposite sex.

I mean it may be possible when you’re an adult or married, but in high school it’s a myth. I had a few friends who were girls and I had fantasized about having sex with every one of them, sometimes all at the same time.

Truth be told, although I had secret crushes on pretty much every girl in school in some sort of way, it was my best friend Ellen I really wanted. Sure, I wanted to have sex with her, but I wanted to be her boyfriend too. The problem was she had a boyfriend already and he was better looking than me, more athletic than me and way more popular than me.

I wouldn’t label myself as a nerd per se, but many would.

Ironically, Ellen was academically a nerd. I mean she had the highest GPA in the school, but in her senior year she blossomed physically in all ways: she was taller, her breasts had come in and suddenly boys other than me were paying attention.

I mean I always knew Ellen was beautiful, although she’d hid her beauty with conservative attire, her hair in a ponytail and glasses in a style that didn’t flatter anyone. Yet, as the senior year started, after spending a summer down in the States away from me, she had become a different girl.

The glasses were gone and replaced by contacts.

The long skirts were gone and replaced with shorter, tighter skirts or ass-hugging jeans.

The loose sweaters that had hidden the size of her breasts were replaced with tighter sweatshirts and t-shirts that drew major attention to her impressively large breasts for her small, thin frame.

The braces which she had worn for five years were also gone.

She had gone from cute to a knockout… and my fellow classmates noticed.

I had always been secretly in love with Ellen, but now it was worse as she suddenly became popular and the more popular boys asked her out.

We stayed friends, nothing changed there, but our time together began to dwindle when she got a boyfriend.

Joey.

Fuck.

Joey the quarterback.

Worse, Joey had been my bully throughout school and Ellen knew that. Yet, she insisted he had changed. (I knew from recent experience he hadn’t, but I didn’t want to argue with her or bad-mouth the guy she was in love with.)

So as I continued to languish in obscurity in my senior year, and my longing for Ellen continued, I now had a new emotion… jealousy.

The whole first semester was torture. She dated Joey; she blew Joey; she lost her virginity to Joey; and because I was her harmless best friend she told me everything, oblivious to my unconditional love for her.

This led to my doing a lot of online porn.

Reading erotica.

Watching porn.

Multiple masturbation sessions a day (some even when she was over but busy doing something else, or I was over at her house; we hung out less than the every day of the past few years, but still at least twice a week, sometimes more).

I read lesbian porn the most.

I watched lesbian porn the most, as looking at other guys’ big penises was awkward and made me feel gay.

Then one day I stumbled on some shemale porn. It wasn’t on purpose, I had finished a hot lesbian scene and the next scene that began was a student and a teacher (a plot I always thought was hot; I had imagined myself with a few teachers, but even more I imagined Ellen with some of the female teachers). The scene was a few minutes in, the student making the teacher go down on her at her desk, before the teacher pulled her dress over her head to reveal a big pair of tits, and then pulled her pantyhose down and revealed a big dick.

I was fascinated.

It was big and looked somehow natural on the hot woman… tits and a dick. I had always found a vagina, in pictures and porn, kind of gross and confusing.

But that cock was mesmerizing… somehow completely appealing and beautiful when attached to a woman and not a guy.

Admiring a cock attached to a guy was gay, and gross.

Admiring a cock attached to a beautiful woman was amazing.

The scene continued to surprise me when the teacher changed the hierarchy, switching from submissive to aggressive, as she bent the teen cheerleader over her desk and slid her big dick right into the teen’s asshole.

Anal sex had always seemed kind of weird, but watching a girl with a cock fuck a girl’s ass was hot as hell.

Thus began my obsession with anal sex.

Sometimes it was shemale porn, other times it was strap-on lesbian porn. Then one day as I watched two sorority girls use their strap-ons on a guy nerd who was spying on them… well, I became curious.

I didn’t want to suck a cock, even a shemale’s.

I didn’t want to fuck a shemale or be fucked by a shemale.

I did want to get fucked by a girl wearing a strap-on, which after some research I learned was called pegging.

I was once again fascinated.

I was definitely curious about anal sex, although truth be told being a virgin I was curious about all types of sex (getting a blow job, licking a pussy, fucking a girl), but from this point on all those fantasies, and I had a lot (mostly about Ellen), the main fantasy was now being pegged by a girl, hopefully Ellen.

And that was what I’d been researching, watching and fantasizing about when things all came to a head.

It was Valentine’s Day and Ellen came into my house in tears unannounced at just after six PM. I was watching a pegging scene on my laptop and jerking off when she walked into my room.

She stopped and froze, staring at me caught in the act. I quickly closed my laptop as a guy moaned, “Yes Cheryl, fuck my ass,” and quickly pulled my sweats over my hard-on.

I stammered an apology, even though it was she who had burst into my room unannounced, “S-s-sorry.”

Yet she smiled, even as her face was still wet from tears, “Well, at least someone is getting some action today.”

Although it was awkward, I went along with it, as I waved with my hand, “Rosie never says no.”

She laughed, “Or wants to cuddle afterwards.”

“Or even talk,” I added, before saying, “I think I’ll nip out and wash up.”

“Okay,” she nodded, as she suddenly got sad again.

“What’s wrong?” I asked, delaying my quick exit, humiliation coursing over me, but at least she hadn’t seen what I’d been watching… which was a big bad football player getting pegged by a much smaller nerd when she was supposed to be tutoring him. It was actually a hot scene to see the stereotypical nerd take control and just dominate a guy who is used to being in charge. His whimpers as she took his anal cherry were so hot, as were the moans that began to escape his lips as the pleasure replaced the pain and lastly, I was close myself when he began begging to be fucked harder.

“He dumped me,” she revealed and then crashed into my arms, my still hard cock suddenly poking against her thigh.

“On Valentine’s Day?” I objected, which likely wasn’t the right question, but of all days… what a fucking asshole.

“Yeah,” she nodded, tears rolling down her face and onto my shirt. “I won’t give him my ass.”

My first thought was I’d give you mine. But instead I responded, “What an asshole,” before realizing the irony of the statement.

She laughed, apparently having heard some of the video, “Yeah, I bet he wouldn’t let me fuck his ass.”

My eyes went wide, even though she couldn’t see them, I joked, “A guy should be willing to do anything he wants his girl to do.”

She moved back and asked, her eyes red, “Really?”

I nodded, “I mean if he wants blow jobs he should give you oral too.”

“I wish,” she sighed.

“Never?” I questioned. Now, sure I was a virgin in all senses of the word and thus my experience was nonexistent, but to me the idea of going down on a girl was equally as intriguing as getting a blow job or even losing my virginity, although, of course, lately my obsession had been getting pegged which now superseded all of them.

“He says it’s gross,” she revealed.

Being blunt, hoping maybe one day I would get to go down on her, I said, “I would definitely go down on whoever I was dating.”

“You would?” she asked, genuinely surprised.

“Of course,” I nodded. “I’m a gentleman.”

“So a gentleman goes down on a girl?”

“Yes.”

“Well then, speaking for girls everywhere, you’re a keeper,” she said, wiping the tears from her eyes.

Looking at her dressed up in a pretty dress and nylons, I asked, “Did he just break up with you?”

She nodded, handing me her phone, “Ten minutes ago. By text.”

“Fuck off,” I said, unable to fathom a guy being so unfeeling. I took the phone and read the text.

Sorry babe

But I’m breaking up with you.

“That’s it?”

“Yeah,” she said, shifting from upset to angry, something I’d seen Ellen do on a few occasions. “I want to rip his balls off.”

“And you would be doing girls everywhere a huge favour,” I supported, before adding, “I’ll be right back.”

“Oh yeah, you should probably wash those hands, you bad boy,” she teased.

“You should knock,” I pointed out.

“True enough,” she agreed. “The thought of what I might walk into never crossed my mind.”

“Well, it was bound to happen,” I smiled, trying to play the pathetic angle in a fun way, “I mean I do it a few times a day.”

Not missing a beat in teasing me, she countered, “Only a few?”

“More than two, fewer than twelve,” I countered right back.

She shook her head, “You win.”

“Those are words I never thought I’d hear from you,” I joked.

“And likely never again,” she said, going to the bed and hopping on it, her dress hiking up enough to reveal she wasn’t wearing pantyhose, but those weird hold up things, which were so much sexier and what most of the porn stars wore.

God, how much I loved her. I said, even as I stared at her sexy legs and feet one last time before heading out to adjust my cock and wash my hands, “I’ll be right back.”

I was in the washroom for only two or three minutes, enough time to go pee, wash my hands and settle down my throbbing cock, but that was enough time for everything to change.

I was walking back towards my room when I heard the sounds of the guy begging to get ass fucked.

Fuck.

Ellen was on my laptop.

Ellen was watching the pegging scene I’d been watching when she walked in on me. She was watching so intensely she didn’t notice I was back in the room. Her eyes were big and her expression unreadable.

I stared at her for a long time, unsure what to say, devastated to have her know what I watched. What would she think of me?

“You like getting fucked, my little football slut?” the video Cheryl sneered.

“Yes,” the manly man whimpered, sounding a lot less manly.

Ellen looked up, saw me and said with just the slightest smile, “Interesting video.”

“Beg, bitch,” the onscreen girl ordered.

“I’m sorry,” I apologized, even as the guy responded.

“Please fuck my ass,” he begged. “I need to be fucked by that big Cheryl-cock.”

“Sorry for what?” Ellen asked, not fazed by the kinky scene she was watching.

“Good boy,” the girl responded as she began really fucking him, his whimpers and moans increasing.

“I’m not gay,” I stressed, wanting to make sure she understood that, just as she closed the computer.

“I didn’t say you were,” she said, getting off the bed.

“I’m just saying, I’m not,” I repeated, wanting to clarify completely.

“Get dressed,” she said abruptly. She then added to clarify, “Dress nice. We’re going out tonight.”

“Really?” I asked, this the least likely of all the possibilities I could have imagined.

“Yeah, I’m already dressed up for Valentine’s Day and I want to go out,” she said. She then headed out and added, “Wear a tie.”

“Yes, ma’am,” I saluted, giving a hint to my sexual submissiveness, although she already knew from our years of friendship I would already do almost anything for her.

“Good boy,” she responded back, using the exact words from the video before she walked out.

I got dressed, trying to process what had just happened. She didn’t seem surprised or offended by what she’d discovered. If I could read her mind, which I sometimes could, she seemed intrigued.

Once dressed, I headed downstairs and ten minutes later we were at the movie theatre.

“No dinner?” I asked.

“Too late and all the restaurants would be packed tonight anyway. I’ll get some snacks and we can hit the romantic comedy I was going to make jack-ass take me to,” she said.

“Okay,” I agreed, having watched dozens of romantic comedies with her. Sure they were predictable, sure they were kind of lame, but the smile that always crossed her face when the inevitable happily-ever-after occurred was always worth it.

She preferred the older ones like Sleepless in Seattle, Sixteen Candles, When Harry Met Sally, Say Anything, Can’t Buy Me Love, The Truth about Cats and Dogs, and Clueless, to name just a few I’d watched with her more than once.

She still hadn’t said one word about what she’d witnessed and I had no idea how to bring it up.

We got popcorn and drinks.

We sat down.

We ate popcorn.

Then a few minutes into the movie she leaned her head against my shoulder.

This was new.

I mean she often leaned onto me, even laid her head on my lap when we watched movies at one of our houses, but she had never done anything like this in public.

My confusion increased.

I tried to focus on the movie, but then her hand was suddenly resting on my knee.

I mean it was harmless, but her hand was suddenly just a few inches from my hard cock. One I needed to adjust, but couldn’t without making her move, which I sure wasn’t about to do.

Then halfway through the movie, she sat up, moved her hand to mine and took it into hers. She was purposely holding my hand.

This too was new.

I had never been more confused in my life than I was at that moment and truthfully I was easily confused, especially when it came to women.

Her hand never left mine the rest of the movie, even squeezing when the inevitable kiss happened on screen.

Once the movie was finished, I didn’t move. I didn’t want this strange, confusing intimacy to end.

Alas, it had to.

Her hand left mine when she stood up, but she surprised me once again when she took my hand back in hers and we walked out hand in hand as she talked about the movie like she always did… where people, possibly ones we knew, could see us.

At the car, she asked, “Want to come back to my place for dessert?”

I nodded, “Sure, although we never did have dinner.”

“True,” she nodded, letting go of my hand again, acting like none of this was out of the ordinary.

I adjusted my cock the moment I could, before getting in the car.

We chatted about the movie some more until we arrived at her house.

Once inside, she said, “Go get me a drink of water while I go upstairs and freshen up.”

“You already look amazing,” I said, trying desperately to let her know how much I cared about her.

“You’re a sweetheart,” she said, shocking me yet again as she came over and kissed me right on the lips… something else she had never done.

It lasted only a second, no more, but it had me completely bewildered.

She then walked out, leaving me confused and the hardest I had ever been.

I went and poured her a glass of water and added some ice, poured myself one too, not bothering with ice, which I downed in seconds as I tried to wrap my head around this evening.

It had been a dream come true so far, yet my happiness and excitement seemed to be fragile, as if it could all fall apart in a heartbeat… the pegging video was still lingering in the back of my mind like a big dark Charlie Brown cloud.

I was brought back to reality with Ellen calling down the stairs, “Bring the water up to my room.”

Over many years I had spent hours in her room, with and without her parents’ home, I imagine I wasn’t seen as a threat by them, they’d known me since I was seven, so this wasn’t uncommon.

What was uncommon was what happened when I walked into her room. She was now in her cheerleader outfit, but still wearing the thigh high stockings and her legs were spread open as she lay up on her bed, with some pillows.

I stopped in my tracks.

She smiled and said, as she lifted her skirt, revealing she was commando, and moved her right hand to her pussy, “You said you were hungry and you said you would willingly lick a pussy.”

“I did say that,” I nodded, as I stared at her in a way I often did when she wasn’t looking. She was obviously showing herself to me on purpose so I looked, and here in real life her hairless pussy didn’t look gross or confusing at all, but absolutely gorgeous. Maybe I wouldn’t eat a porn queen’s pussy, but I would definitely eat this one. Was she really offering?

“Jack-ass’s dumping me made me realize something, Jeremiah,” she said, as she slowly rubbed her pussy, making it glisten.

“What is that?” I asked, unable to move, unable to break eye contact with her hand between her legs.

“I should date a good guy; I should date someone I already love,” she revealed.

“You love me?” I asked.

She asked back, “Don’t you love me?”

To my surprise her tone was one of insecurity. I quickly blurted out the words I’d been bottling up for years, “I’ve always loved you, Ellen.”

She moved her hand away from her pussy, got off the bed and walked up to me.

I remained in a frozen state of bewilderment as she stood in front of me and kissed me. Unlike the quick kiss in the kitchen, this one was intimate. I was so paralyzed with shock, this being my first romantic kiss with anyone, I didn’t respond back.

She broke the kiss and said, in her sincere playful way, “Kiss me back, dummy.”

I went to say sorry, but her lips were already back on mine. This time I kissed her back. Even though I had never kissed anyone except duty kisses with family, it felt so natural.

At first, it was soft and tender.

Then it became more urgent, especially when her tongue was suddenly in my mouth, which felt really weird.

I did the same thing, just moving my tongue in her mouth with no map or purpose.

When she broke the kiss, she asked, a wicked smile crossing her face, “Want to kiss my other lips?”

“I want to do everything with you,” I answered.

She took my hand and led me to her bed. I followed like the love-sick puppy I was. She got back into the exact same position I’d walked in to and I instinctively got onto the bed and lay between her legs, looking up at her. I moved my hands down both her nylon-clad legs, something I’d also fantasized doing for years. She always wore pantyhose, I had many times gotten brief touches of them, but never like this.

She seemed to know this as she asked, “How long have you wanted to feel my nylon legs, Jeremiah?”

“Is forever too long?” I joked, “you got some for your fourteenth birthday and you’ve been tantalizing me with them ever since,” moving my hands back down her legs and to her feet.

“Are you a leg guy or a nylon guy?” she asked, as my hands went to her left foot.

“How about a nylon foot guy?” I asked, as I massaged her perfectly manicured feet with my hands.