Whats a Little Anal Between Friends

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Author's note:

This story is meant to be a fantasy. As such, many points of reality are put to the side, such as safety and pregnancy, as well as others.

Additionally, this story will cover a wide range of sexual activities. I will try to cover them in the intro, but please be aware. All characters are at least 18 years of age.

Following comments that I have gotten previously; Everything here is meant for the purpose of telling a story and titillating the reader and is not meant as a portrait of reality. I love hearing from readers, but if you comment that it wouldn't happen that way in real life, well, that's why it's a fantasy.

Topics: crossdressing, anal

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"I can't fucking believe she cut me off like that, especially after I ate her stupid cunt to three orgasms!" Billy complained to me. "She keeps doing it, and refuses to do anything at all if I don't start with her."

"That's because she is a bitch and is using you," I responded for the fourth time since we sat down. "You should just dump her and move on."

"I should," He finally admitted. "But the problem is that when we do have sex it's amazing, and if I leave her I need to go completely without."

"You can find someone else," I responded, cracking another beer, my third of the night since Billy showed up at my apartment earlier that evening.

"As hot as Becky? Like you have?"

"Hey, I've dated some."

"Oh yeah? When's the last time you got laid?"

I didn't respond, as it truly had been a while.

"That's what I thought. So unless you have someone in mind who is willing to lift their skirt for me, I'm just going to keep hoping that Becky eventually stops being so selfish."

A week later, Billy called me to come over. He was fuming and already half in the bag.

"You got your wish. The stupid cunt left me after I called her selfish," He complained as he poured me a drink.

"You are better for it, man."

"Well it's your fault," He said, knocking back another shot.

"Why is it my fault?"

"Because you are the one who kept pushing me that I could do better."

"I'm not accepting responsibility for any of this mess."

"Fuck you," He said, tossing me a controller.

We spent the next two hours drinking and playing playstation.

"I'm so horny that at this point I would fuck anything in a skirt, regardless of how they looked," Billy complained at one point between games. "Hell, I'd even fuck you if you were wearing one."

"What the fuck does that mean?" I asked offended, drunk enough not to be sure what I was even offended about.

"I mean that I'm so horny that if you were wearing a skirt I wouldn't care what you looked like and I would fuck you."

"Oh really. And who says that I would let you?"

"Of course you would. What's a little anal between friends. Besides, if you did then I would return the favor."

"I can't believe you said that. What's a little anal between friends. Come on."

"No man, I'm serious. Now that I think of it, it's the perfect solution."

"Fuck off. You're crazy."

"No really. Think about it. We get to have sex without all the strings attached of having a girlfriend."

"I'm not gay and I like pussy."

"Nothing is stopping you from going out and getting some. But until you do, would you prefer to keep fucking your hand?"

At this point I was drunk enough to be trying to come up with excuses instead of just saying no. "Well it's a moot point, because we don't even have a skirt."

"Actually, I might. Hold on," He said scrambling to his feet and heading to his bedroom. He came back a minute later holding a bundle of clothing. "Becky left some stuff here a few weeks ago and I washed it for her, but she never took it back."

Billy held out the bundle to me.

"Why do I need to go first?"

"Because it was my idea, and I'm the one who was left hanging tonight. Also, you probably jerked off before coming over."

He was right. I had masterbated just before coming over. I sighed and grabbed the bundle.

"I can't believe I'm doing this," I said as I headed to the bathroom.

I couldn't believe what I was doing as I got undressed and separated out the different items Billy had given me. Becky was smaller than I was by a bit, but she did have a large ass, which I hoped meant that her skirt would fit. Or maybe I hoped it wouldn't. At that point I was drunk enough that I wasn't sure. Holding up the black skirt in front of me, it seemed to be big enough that the stretchy material would let me get it on. Then I noticed the bit of red lace that had fallen out when I picked up the skirt. Picking it up I found myself holding a pair of red lace panties.

"Fuck." I said to myself as I held them up.

Even as I stepped into them, I wasn't sure why I was doing this. I wasn't sure if I was trying to prove something to Billy, call his bluff, or was it that a part of me thought that maybe this was actually a good idea. The panties were snug, tight on my ass and they didn't really have space for anything up front, but not uncomfortable. I pulled on the skirt over them and tried to put on the shirt as well, but it didn't fit. I pulled my own t-shirt back on and walked out.

"Still think you'd fuck anything in a skirt?" I asked Billy.

"Hmmm. Maybe. I'm not sure. Come here."

Billy had me bend over the side of the couch. I complied, still unsure of my own motives. I felt Billy pull the bottom of the skirt up, exposing my panty-clad ass.

"Honestly," Billy said, "I'm going to have to say yes based on what I'm seeing here."

Before I could respond I felt Billy pull down the panties until my ass was exposed. I heard something open and then something cold pressed against my asshole. My eyes got wide as I felt my anus being penetrated.

"What? Are you? Is that?" I asked, not able to get a full sentence out.

"Relax, it's just a finger. I need to stretch you out," Billy responded as I felt the intruder slide deeper inside of me.

It felt more weird than anything else, having my best friend finger my virgin asshole, especially after I had a moment to get used to it. Then he added another finger. And then another. As the third finger pressed inside of me, the feeling turned to one of stretching, especially as he pushed them deeper after a few shallow thrusts. I gasped as my asshole was pried open. Once the three fingers were sliding in and out freely, he started twisting them around as he went in and out. The twisting added another level of sensation, stretching me in different directions. When he finally pulled his fingers out of my ass, it almost felt like something was missing. I had no idea how long I had been laying there having my ass played with. It both felt like seconds and hours.

By this point I wasn't sure if I wanted to continue. I was drunk, confused and very nervous. Before I could get up or even put together a coherent sentence, I felt something pressing against my stretched asshole. With less resistance than I had expected, my ass was virgin no longer. Billy groaned as my ass stretched around the head of his cock.

"God, you are even tighter than Becky was," He moaned as he slowly worked his way deeper inside of my colon.

I could feel him getting deeper and deeper with each small thrust. The feeling of stretching and fullness was bordering on the uncomfortable. I was going to say something, to ask him to stop, when suddenly my eyes went wide. In theory I knew that anal sex was supposed to feel good for people with a prostate. Theory aside, I had not thought about, or expected, the jolt of pleasure that coursed through my body. My own dick, trapped in lace as it was, snapped to full hardness, as the dick in my ass pressed against my prostate. Any thoughts of me telling Billy to stop were obliterated by the pulses of pleasure sent each time his cock shifted inside of me. I finally felt his thighs press against my legs. A part of my mind was crying out that this was wrong. That I shouldn't be wearing panties and a skirt. That I shouldn't be letting someone fuck my ass. But the rest of me was overcome by the electric feeling of being stuffed full, stretched out, and having a magic pressure button inside of me get pushed over and over again.

Billy pulled back and then thrust forward, going deep inside of me in one motion. I gasped. By this point, Billy was focused on himself, having ensured to his satisfaction that he wasn't going to hurt me. He began fucking my ass for real. I couldn't stop the moan that escaped as he pounded my ass.

"That's right, girl," Billy moaned from behind me. "Feels good when I fuck you hard, doesn't it?"

I couldn't believe that Billy had called me a girl, but it didn't matter. All that mattered was the feeling in my ass pushing me closer and closer to orgasm. Billy's thrusts became more urgent and erratic, his hands on top of the skirt gripping my hips, his thighs slapping against mine. It felt like we were in a race to the finish and I was worried that I was going to lose. Then suddenly it happened. I let out a strangled cry as my cock started twitching and spraying cum into the red lace that held it. My ass tightened around the thrusting erection inside of it with each spurt, making it feel even bigger inside of me. Billy must have appreciated the extra tightness as he suddenly groaned and I could feel him painting my insides with his cum.

When Billy finally pulled his dick out of my ass I felt empty and weird. Suddenly the rush to the high was gone. The post nut clarity left me feeling very confused. I quickly got up and hurried to the bathroom to get cleaned up and changed. I took my time, trying to both process what had happened and not think about it, ask at the same time. I eventually left the bathroom, wearing my own clothing, anxious and feeling awkward. When I got to the main room, Billy was sprawled out on the couch I had been bent over, looking relaxed and content, playing a game.

"That was great, man. Thanks. You good?" He said glancing up as I walked in.

"I guess?" I said, shrugging.

"It sure seemed like you enjoyed it."

"Let's see what you say tomorrow," I responded trying not to sound defensive.

"Yeah yeah," He said tossing me the other controller. "Now are you going to just stand there or are you going to sit and play?"

Dropping down to the couch, it wasn't long before we settled back into our normal banter. By the time I left, the awkwardness that I had felt after being fucked had faded. I had grabbed the skirt and cum stained panties on my way out. I threw them in the wash when I got home.

My dreams were mixed up and confused. I woke up nervous about the evening's plan for many reasons. First and foremost, I wasn't sure if Billy was actually going to go through with it. Not that I didn't believe him, but he sometimes talks a bigger game than he actually is willing to do. Second, I didn't want to ruin our friendship and if I hadn't been drunk the night before, I would have probably not been willing to risk it. And finally, something which I would never admit to Billy, but I had never had anal sex before. None of my girlfriends had ever been willing.

An hour after I got up, Billy messaged me.

"What did you do with the clothes?"

"Took them home to wash them so that they would be clean for you tonight."

He sent me back a thumbs up.

Work was a mess. I couldn't concentrate on anything. I had to redo things multiple times. When I finally called it a day it was a relief to get into my car. Billy often worked evening shifts, so I knew it would be a few hours before he showed up. When he finally did I was deep into the PlayStation game that I was currently obsessed with.

"Do you mind if I grab a drink and chill for a bit?" He asked, dropping his bag by the door. "Work was a bitch today."

"Go for it. There is food in the fridge from my dinner if you want."

"You are a godsend."

The next two hours passed in the same way we spent at least half of our evenings. Sitting on the couch, chilling and playing, talking shit about our bosses and stupid clients. I had just beaten him for the third time in a row when he dropped the controller to the side, threw his head back and signed.

"Fuck me! I don't get how you always win like that!" He complained.

"It's because I'm better than you," I teased him. "But since you asked so nicely, I'd be happy to fuck you, especially after owning your ass like that."

"Smart ass. Fuck you."

"No no. It's my turn."

"I know. I know. Where is the skirt?"

"I left it on my bed."

Two minutes later Billy was back, wearing the skirt. It honestly looked ridiculous on him. I smirked.

"Yeah yeah. Laugh it up. You didn't look so great in it yourself," He said.

"You seemed to think that I looked good enough in it last night."

"That was only once you were bent over and I was looking from behind."

"Then I guess there is only one way to compare. Come on," I said standing up and heading back to my room. "Kneel on the bed."

He got into position and put his face on the mattress. I grabbed my blanket and pulled it over his back. From this angle, I really couldn't tell that the ass that was sticking up belonged to my best friend Billy.

"Honestly, from this angle, you don't look too bad."

"Thanks asshole," came the muffled response.

Lifting the skirt, I revealed the red lace that stretched enticingly across the ass in front of me. I ran my hand across it and felt Billy shiver in response. I stopped myself and took a deep breath. I needed to reframe This in my mind. This wasn't Billy. Billy didn't wear a skirt or red lace panties. I wouldn't fuck Billy's ass, because that would be gay.

"Betty," I said aloud.

"What?" Came the response from under the blanket.

"Betty. That's the name of the girl who this ass belongs to. That's the name of the girl that I have in my bed right now that I'm going to fuck."

Billy didn't respond, which was good.

I gently peeled back Betty's panties, exposing her asshole. Grabbing the bottle of lube I kept next to my bed, I applied a generous dollop to her dark star. I pressed the pad of my finger gently against her anus. There was a bit of resistance before my finger slid inside up to the first knuckle. Betty gasped at the intrusion, but didn't move. I slowly shifted my finger back and forth, feeling the tightness and the way it held my digit. I couldn't even imagine how good it would feel around my cock and had to stop myself from rushing.

I pulled my finger out of Betty's ass, making her moan at the loss. I added more lube to her entrance, making sure it was nice and slick. I pressed two fingers against her anus, feeling the resistance before they slid inside. Betty gasped at the intrusion, but didn't move. I slowly shifted my fingers back and forth, feeling the tightness and the way it held them.

"You ready for more?" I asked, my voice husky with desire.

"Yes," Betty replied, her voice strained.

I added a third finger, feeling Betty's body stretch to accommodate me. She moaned, her hips moving back to meet my fingers. I started to thrust my fingers in and out, fucking her with them. Betty's breathing hitched, her body tensing as he got closer to the edge.

"Fuck, Luke," Betty moaned, her voice strained. "I'm gonna come."

I pulled my fingers out of her, making Betty moan at the loss and the sudden lack of sensation. I added more lube to my cock, making sure it was slick from base to tip. I positioned myself behind Betty, my knees on either side of hers. I grabbed her hips and pressed the tip of my cock against her entrance. I pushed forward, feeling the resistance give way as I slid inside her. Betty hissed as I filled her up, her body adjusting to my size much more easily than mine had to Billy.

I grabbed Betty's hips and started to thrust, my hips slapping against her ass. Betty's head was down and covered by the blanket, but I could see her hands fisted in the sheets. I could hear the slick sound of my cock sliding in and out of her, the only sound in the room aside from the gentle grunts and heavy breathing. I reached forward and grabbed a handful of the red lace panties, using them as leverage as I fucked her harder.

Betty's breathing hitched, her body tensing as she got closer to the edge. I could feel my own orgasm building, my balls drawing up tight. I could feel Betty's ass clenching around me, her body trying to pull me deeper inside her.

"Fuck, Luke," Betty moaned, her voice strained. "I'm gonna come."

I couldn't hold back any longer, my orgasm crashing over me like a wave. I groaned, my cock twitching as I filled Betty up. Betty's orgasm followed moments later, her body shaking as she came in her panties. I collapsed onto Betty's back, my breathing heavy.

We lay there for a few minutes, both of us trying to catch our breath. I pulled out of Betty and got up, making my way to the bathroom to clean up. When I got back, Billy was still in the same position, his head still down.

"You good?" I asked, my voice still rough from my orgasm.

"Yeah," Billy replied, his voice muffled.

I didn't say anything else, just got dressed and left the room. I could still feel the ghost of Betty's ass around my cock, the memory of the way she felt making my cock twitch. I didn't know what this meant for us as friends, but I knew I wanted to do it again.

I was back on the couch and playing again when Billy walked back in. He sat down gingerly and didn't say anything. I handed him the other controller and it took three rooms before he said anything.

"So if my ass belongs to Betty, who does yours belong to?" He asked, not looking at me.

"I think Lucy."

"Makes sense." After another few minutes of silence he spoke up again. "We good?"

"Yeah."

"We going to keep doing this?"

"I'm in. You?"

"Yeah."

It took two weeks for us to order another couple of skirts, as well as a dozen pairs of panties each. I won't say that we fucked every night, especially after the initial rush settled down, but except for when one of us was in a relationship, not a weekend went by without me calling Billy to see if Betty was available, or him checking if Lucy was.

It turned out that having sex regularly made dating less stressful. Apparently, knowing that even if you struck out, you were getting laid no matter what, gave a guy the kind of confidence that women liked, which meant that as time went on, both Billy and I actually had dates regularly. We rarely progressed to the level of relationship which would have required us to abstain. At least not until I met a girl who fucked my ass on the first date, but the story of how I met my wife is for another time.