[F21] – First Anal Experience

“I hear you!” I called across my apartment, “I’m just getting some things cleaned up, changing, then we’ll meet up with you downtown,” I explained to Cara who was chiding me for being a flake.

“Ok, but you better not bitch out on me again!” Cara called as she was ushered out the door by the large group of people leaving to head to the bars.

Within minutes my apartment had gone from a bustling party to deserted apart from my roommate Rachel and my friend Brian who had hung back to help us clean and walk with us downtown.  In reality, I didn’t understand the move.  We had plenty of beer to go around, and the walk downtown wasn’t a short one to make.  I had been content to spend the evening hosting everyone for the sole reason that it meant I could easily sneak off to my room and pass out whenever I felt like it.  Now the evening felt like a far bigger hassle than it had been worth.

Rachel stood in the doorway to her room, her freckled nose scrunched up in a scowl as she tugged at a curl of red hair, “so, someone want to explain to me why we’re leaving?” she asked, “We spent like $200.00 on beer and everyone was here for all of 2 hours.”

“I think it was Cara’s doing,” I replied, “she’s always like this.  She hates apartment parties and is always trying to recruit everyone to make the move to the bars.  She just hates beer and likes the attention she gets downtown when guys buy her free drinks.”

“Well that’s stupid.  What the hell are we going to do with all the beer that’s left over?  I’ll bet we have, like, 90 beers in there still!” Rachel complained.

Brian, who, had been scrambling around the apartment picking up empty cans, shot glasses, and solo cups in an effort to clean everything up, opened the fridge and grimaced, “Eh, I think you’ve got more than 90 left.  There’s at least 2 cases unopened in here, plus a solid 15 loose, and I believe you still have 2 more cases sitting out on the balcony.”

“Awesome.  What the hell do we do with all of that?” Rachel groaned.

“You could always have another party?” Brian suggested.

“Fuuuck that!” I replied, “this one was as big of a pain in the ass as I’m willing to deal with.  We’re just going to have to take cases to parties with us and pawn it off on people.”

“Ok, but I’m not about to go downtown and spend more money on alcohol when we already spent so much on the stuff we have here,” Rachel argued.

“Agreed.  Fuck Cara.  I’m texting her and telling her we spent too much on the booze that’s here to justify spending more going downtown.  We can stay here and have a quieter than expected night in,” I said, resigning myself to the backlash I was sure to get.

“Perfect!  Ok, I’m changing into comfy clothes then,” Rachel chirped, dashing off to her room.

“You guys care if I hang out too?” Brian asked, “My place is a hell of a lot closer to here than downtown and it’s not like I knew anyone but you two anyway.”

“For sure!  I’d be mad if you ditched us anyway!  We need your help to do some damage to all this beer!” I laughed before heading to my room to follow Rachel’s lead and change into something more comfortable.

Brian and I had met freshman year in one of our gen-eds.  He had quickly become a good friend and someone I could rely on in any number of situations.  On multiple occasions he had come to rescue me from potentially embarrassing or dangerous situations simply because my text messages had become nearly incomprehensible in my drunken stupor.  Rachel had always pestered me about him, wondering why the two of us weren’t dating, and while Brian was intelligent, kind, attractive, and overall a great guy, I just didn’t feel that way about him.

After quickly stripping out of my jeans and top for a pair of cotton shorts and a tank top, I popped back out to the kitchen where Rachel was sitting at the kitchen counter with three beers ready, “Ok, I have a request,” Rachel began, a smirk on her face, “There’s a drinking game that, like, EVERYONE has played, but I never have, and I wanna play it,” she continued, “I know it’s cliche and everything, but can we please, please, please play a little bit of truth or dare?”

Brian laughed as he finished drying the last of the shot glasses and joined us at the counter, “that’s not actually a drinking game,” he pointed out, “people just usually drink while they’re playing it.  That’s why it’s popular in high school cuz you can play it stone cold sober, which, I have to say, makes for a VERY awkward vibe if there’s no social lubricant to help grease the wheels.”

“Yeah, you’re really not missing anything,” I told Rachel, “It sounds way more fun than it actually is.  Usually it just ends up with people saying ‘umm’ for ten minutes while they try to think of something.”

Rachel scowled, “It sounds like you two have just played with people that are super lame.”

I laughed, thinking back on the few times I had played, “Oh, no, people ask or dare people to do crazy stuff, it’s just no one will actually do it.”

“Oh…well, can we at least play like two or three rounds so I can say I’ve played, then we can move on to something else if it sucks?” she asked, sipping at her beer.

I sighed, “Fiiiine, just so you can see how dumb it is,” I conceded, not worried in the slightest about just a few rounds.

Rachel was her typical bubbly self, excited and antsy for a new experience.  She had been my roommate for the past 2 years and we had grown very close during that time.  She was the typical nerdy type, from the intelligence and major all the way down to her appearance.  Her red, curly, shoulder length hair was paired with a freckly nose, very slight frame, and alabaster skin.  However, she was not the typical nerd in her dating life.  She had gone through a slew of guys in our time together, discarding one after the other as she got bored of them, regaling me with stories of their sexual prowess or inadequacies, allowing me to live vicariously through her.  

“Hold on to your hat baby cakes, cuz you’ve never played truth or dare with me!” Rachel warned, slapping the counter with excitement, “and since it was MY idea, and it’s MY first time playing, I think I should get to go first.  So, Mary, Mary, quite contrary, truth or dare?”

I took a deep breath, taking a sip of my beer, “truth.”

“LAME!” Rachel mocked, laughing, “Ok, truth, umm, lets see…Oh! Ok, this is a good one.  Miss Martinez, if I were to go into your room and rummage around, what sex toys would I find in there?” she asked, leaning in with anticipation.

Brian’s eyes went wide, “Oh damn, you’re really going to make the most of these couple rounds aren’t you?”

Immediately I felt my face burn with embarrassment.  I knew Rachel was aware of at least a few of my toys, as we had discussed them at length previously,  however, there were a few items that I found to be a bit more personal and had held back during our conversation.  In a quick decision, I determined that a game of truth or dare wasn’t a good enough reason to suddenly reveal my additional predilections. 

“Ok, well, uhh, you pretty much know all of them, so I’m not sure what new information you’re going to get out of this, but I’ve got the vibrator and a dildo,” I replied, trying not to sound too nervous about the question.

“Liar!  I know there’s more than that,” Rachel said with a smirk.

In a moment of panic, I decided to reveal a few additional items I had to try to satisfy her curiosity, “Ok, well, yeah, I also have handcuffs and some restraints that go under the mattress, but I wouldn’t call those toys,” I defended, trying to justify my omission.  

“Oh Mary, I didn’t know about the restraints!  That’s fun.  What I’m talking about is another toy.  One I saw on your night stand a few weeks ago when I popped in to ask you about breakfast,” Rachel explained.

My brow furrowed, trying to recall what she might have seen, “I don- Oh!” I suddenly remembered, having almost forgot the moment when I realized I had left one of my butt plugs out and panicked about whether Rachel had noticed or not, “Fuck.  Ok, fine, yes, I also have a plug,” I confessed, not divulging that I actually owned an entire set.

“Mhm, and what kind of plug?” Rachel prodded, trying to push my buttons.

“Oh c’mon, there’s only one kind,” I barked back, slightly annoyed at having had to reveal more than I ever wanted to.

“Oh really?  And what kind is that?” she persisted.

I sighed, rolling my eyes, “A butt plug.  Happy?” I answered.

“Oh ecstatic,” Rachel mocked with a grin.

I never thought he would judge me in any way, but it was simply a level of information that I didn’t need Brian to know.  In fact, it was information that no one had known until now.  I had kept my infatuation with anal play entirely to myself and had wanted it to stay that way.  Unfortunately, my nosey roommate had decided that a stupid drinking game was just the time to out me.

“Ok, my turn then,” I said, pushing forward to try to move the attention off of me, “Rachel, truth or dare?” I asked, ready to take my revenge for her probing question.

Rachel laughed, “I don’t like that look in your eye.  I’ll play it safe and go truth.”

I had banked on the fact that she wouldn’t risk a dare and had a question ready that would more than even the playing field when it came to divulging our sexual interests, “Ok, Rachel, how many times have you been fucked in the butt?”

Rachel blushed fiercely, her face nearly the color of her hair, “Ok that’s not fair.  You know why the number is so high,” she argued.

“And how high is that number pray tell?” I smirked at her embarrassment.

Rachel turned to Brian, desperate to explain, “Ok, you have to understand, my mom wouldn’t let me go on birth control in high school cuz she thought I’d immediately start having sex, which, I totally would have.  But I was terrified of getting pregnant, and I’d heard horror stories about condoms breaking, so I just went for the next best thing.  So, for like, six months, my high school boyfriend and I were anal only.  So that’s why the number is probably like…I dunno, a hundred?” she guessed, still blushing.

Brian shrugged as if it were perfectly normal, “I can understand that.  Horny teenagers are going to find any way possible to fuck around, at least you thought it through,” he laughed.

I had to admit, I was a little disappointed at how casually Brian accepted this new information about Rachel.  I had hoped he wouldn’t be so understanding, despite him having always been understanding of whatever predicament I had gotten myself in.

“Wait, hold on,” I paused, doing some quick mental math, “Six months, 30 days a month, that’s 180 days.  You were doing anal every three days?!” I asked, having known about her previous adventures, but not to the extent of her numbers.

Rachel blushed again, “Well, I mean, no, not every three days.  Maybe like once a week?  But…Ok, fine, like 30 of those have been after I got to college with other guys.  What can I say, I enjoy it!  Which, if you have a butt plug clearly you do too!” Rachel snipped, pulling me back into the forefront and causing me to blush again.

“Ok fine, whatever, it’s your turn,” I replied, pushing her to move past all of this anal talk.

“Ok, Brian needs to get in the game, we’ve learned enough about us,” Rachel chimed, turning her attention to the tall, brown hair, blue eyed guy standing innocently next to us, “truth or dare?”

“Well, why ruin a good streak when you’ve got one going?  Truth,” He replied with a smile.

Rachel sighed, “Someone is going to have to not be a coward and pick dare, otherwise this is just a game of revealing sexual tendencies,” she laughed.

“Yeah, see, that’s all this game ends up being usually,” I pointed out, reminding her of what Brian and I had said earlier.

“Ok, well, you know about our past with it, might as well know about yours, how many times have you done anal?” Rachel asked.

Brian laughed softly, “I had a feeling the theme would continue,” he replied, “Umm, I dunno, maybe thirty times?” he guessed.

“Ok, ok, that’s a respectable number.  Must have had a girlfriend that was into it if you’re that high,” Rachel surmised.

“Yeah, one very short term, and one a bit longer that only enjoyed it when she was drunk,” he replied.

“Really?  Anyone I would know?” I asked, curious to hear if it had been any of the girls he had brought out with us over the previous few years.

“Remember Kate?  She was the one that only liked it when she was drunk.  And Amy.  Amy was a fiend for it and wanted it like, daily, but we only lasted like 3 weeks cuz she turned out to be a psycho,” he laughed.

“Kate?!  Really?!” I replied, shocked, “I NEVER would have expected that.  She seemed like such a goody two shoes.  She was always so quiet and innocent.”

Brian shrugged, “Yeah, she was a totally different person when we were alone.  She just didn’t like going out or hanging out with people much,” he explained, “Ok, Mary, truth or dare?” 

“Wait, I just went!  It should be Rachel’s turn!” I protested.

“And I thought I got to pick whoever the hell I wanted,” Brian smirked.

“Ugh, fine,” I conceded, chewing at the inside of my cheek as I stared Brian down.

Brian was the creative type.  Someone who never ceased to come up with unique solutions to problems or think about things in a way I had never considered.  That particular trait of his worried me in a game like this.  I didn’t want to underestimate his ability to come up with a question that would be unparalleled in its ability to make me squirm, however, the same was true about his ability to come up with dares.

After careful consideration, I determined I would rather answer an embarrassing question than DO an embarrassing act, “Truth.”

“Ok, simple and easy, a truth or dare classic, where’s the most unusual place you’ve had sex?” he asked.

I laughed, “Uh, ok, don’t judge me, but, the bathroom at Mack’s,” I answered, cringing at the memory from freshman year.

“Mack’s?!” Rachel shrieked, “PLEASE tell me this guy was a 12 out of 10 gorgeous, cuz those bathrooms are NASTY!”

I shrugged, “He was ok?  I was drunk so I don’t really remember him all that much.  I just know we were making out in a booth, he suggested we go back to his place and I didn’t want to go outside because it was cold, so I suggested the bathroom.  I just dragged him in there, hiked my dress up, bent over against the wall and he did the rest,” I explained.

“Ew, ew, ew, that’s so bad!  How did I not know this story?!” Rachel asked, miming a puking motion.

“I dunno.  I hadn’t really thought about it in a while,” I replied with a laugh, “Not my proudest moment.”

Brian shook his head in mock disgust, “Clearly not.  At least you did it standing up.  There are diseases on those bathroom floors that haven’t been discovered yet.”

I laughed, “Ok, Rachel, truth or dare?”

Rachel paused a moment before sighing and firmly placing her hands on the countertop, “I guess I’ll be the one to break the seal.  Dare.”

“Ooo, ok Mary, her fate is in your hands, are you a cruel or benevolent ruler?” Brian asked.

I thought for a few moments, coming up with two ideas, one of which seemed a little too intense and the other a bit too soft, “Ok, I’m leaving this up to you Rachel since you’re the one that wants the game to be spicy.  I have one dare that’s like a 5/10 on the spicy scale, and another that’s probably an 9/10.  Which one?”

Rachel took a deep breath, “Whoo, ok, umm, I guess the question is what’s a 5 on your spicy scale?  Some people’s 5 might be strip totally naked and others might be finish your beer.”

I shrugged, “that’s up to you to try to figure out!  I’m not giving any hints,” I replied with a grin.

“Mmm, dammit,” Rachel mused, considering her options, “Ah, fuck it, I don’t want to be one of the boring people you’ve played with in the past.  Give me the 9/10.”

I grinned ear to ear, knowing she wasn’t about to do what I was asking of her and she would have to become one of the boring people she had just mocked, “Ok, remember like 3 months ago, just before you and Sean broke up?  You got a package.  You said you never got to wear it because the two of you had broken up before you had the chance.  How bout you go put that on?” I smiled, trying to look innocent and sweet while knowing I was being anything but.

“You mean?”

“Yup, you know exactly what I mean.”

“Oh c’mon, seriously?!  I showed you what it was!  That’s like…you remember what that looks like?!” she argued, trying to change my mind.

“I DO remember, and I remember saying you’d look sexy as hell in it, and I think it’s a shame it’s just been collecting dust since then.  So?  Do you accept my dare, or are you going to be one of those lame people?” I teased.

That was enough to push Rachel’s competitive streak into overdrive, “Fine, fuck it.  Brian, I hope it’s your birthday soon, cuz you’re about to get quite the present,” she said, marching into her room.

“Uh, care to fill me in?” Brian asked with a laugh, “What exactly is she putting on?”

I smiled from ear to ear, shocked this was actually happening, “Oh, she bought some super slutty lingerie for Sean’s birthday a while back but she never got to wear it.”

“Ah, well then, lucky me,” Brian laughed, clearly happy with the sudden turn of events.

“Hey!  Mary!  While I’m changing, truth or dare?” Rachel called from behind her closed bedroom door.

I laughed, “I feel like a dare would be a bad idea for me at the moment.  Let’s stick to truth!” I called back, not wanting to feel the ire of Rachel after having just given her such an intense dare.

“You sure?” Rachel replied in a tone that was slightly concerning.

“Uh, I think so?”

“Mk, how bout you tell Brian all about that dream you had last week!” Rachel called back, laughing sadistically.

The blood drained out of my face, “DARE!  DARE!  I want a dare!” I called back in a panic.

The previous weekend I had confided in Rachel over breakfast that I had had a VERY graphic sex dream about Brian.  It had been the type of dream that felt so real in the moment and I had woken up in a puddle of my own creation.  The dream had been intense and sexy in all the ways I could have wanted, but also in all the ways that would make it immensely embarrassing to tell the subject of the dream about.  There was simply no way I could sit across from Brian and explain to him how he had fucked me, even if it was just a dream.

Rachel laughed like a giddy school girl from her room, knowing she had won, “Ok, but technically you aren’t allowed to change. I’ll just allow it this ONE time!” she replied, “An eye for an eye!  Go in your room and pick out the sexiest lingerie or set that you have and put it on!” she called back.

I buried my head in my arms on the countertop, my whole body flushing as I considered whether to just end the game right there.  I couldn’t possibly do this.  Not with Brian right there.  If it were just Rachel and I, then sure, no questions asked, but it was a totally different matter with a guy sitting 2 feet away.  I also knew I would never hear the end of it if I backed out.  Finally, I made my decision and pushed back from the countertop.

“Ok, I’m changing, but then game over.  I think we’ve pushed the boundaries enough for one night don’tcha think?” I called to Rachel through her door.

“What?! No!  We can’t end there!  If we end there then this is the most lopsided victory in history!  Brian gets to see us nearly naked and he’s answered one question?!  Absolutely not!  Also, this shit is complicated to put on with all these straps.  If I’m putting it on, it’s staying on for longer than 30 seconds,” Rachel yelled through her door.

Brian stood at the counter, a bemused look on his face, “Hey, I’m totally fine with ending the game now,” he said with a laugh.

“Of course he is!” Rachel called, “Brian, we’re not done here til we see a hell of a lot more skin!”

Brian shrugged, holding his hands up as he pleaded for innocence, “I don’t believe I was the one that dared EITHER of you.  I’m an innocent bystander in this whole thing,” he argued.

He wasn’t wrong.  Rachel and I had certainly been the ringleaders of the entire game and how intense it had gotten.  However, Rachel was also right in that Brian was about to get quite the show, with absolutely no return on our end.

I considered the options for a moment and eventually came to the conclusion that if Brian was going to see me in my underwear, it didn’t really matter if it was for 30 seconds or for 10 minutes, and the 10 minutes might allow Rachel and I to even the playing field.  My competitive streak had gotten the best of me, and I wasn’t about to lose quite this terribly.

“Ok, game on then!” I called to Rachel, “We keep playing until we think it’s an even trade!”

“Yeah!  That’s my girl!” Rachel replied as Brian’s head fell back, staring at the ceiling in defeat.

I left for my room, closing the door behind me.  I didn’t need to think about what I was going to wear.  Every girl has their go-to attire when they know there’s a chance they might get laid that night, and I was no different.  I quickly shed my cotton shorts and underwear, as well as my tank top.  I let out a heavy sigh, steeling my nerves for what I was about to do.  I slipped my feet into the white lace thong and pulled it up into place before hooking the matching bra together and spinning it around into place.  

White had always been a good color for me.  With my Columbian heritage, my tanned skin offered a nice contrast to the bright white of the matching set, as did my black, shoulder length hair and brown eyes.  I gave myself a brief once over in the mirror, seeing if I could adjust the garments any at all to allow the lace to hide even a little bit of my nipples or pussy.  In the end, it wasn’t meant to hide much at all, which is sort of the reason I had bought it, and I resigned myself to putting my entire body on display for one of my best friends.

As I surveyed myself in the mirror, I heard the door to Rachel’s room open and the soft patter of her steps as she walked out into the kitchen.

“Damn, you look….I mean, Sean has to be the unluckiest guy on the planet to have missed out on that,” I heard Brian comment.

“Aww thanks!  That’s sweet, but he deserves to have missed out.  He was an asshole at the end,” Rachel replied, “Hey sweet cheeks!  You almost ready in there?  I know yours can’t possibly take as long as mine did!” she called to me.

“Yeah, yeah, I’m coming,” I replied with a sigh before opening the door.

Rachel let out a whistle as I stepped into the kitchen, “Damn girl!  Give us the 360!” she insisted as I twirled in place for them, “Can I just say, it always makes me sad when I hear about a girl with an ass to die for, but she doesn’t use it.  It makes me happy knowing you use that thing,” Rachel grinned.

“Oh I don’t use it.  I have a toy, that’s it,” I corrected her.

Rachel winked, “Oh, give it time.  The toy is just the gateway drug.”

I handwaived her insistence before turning the attention on her, “Enough about me, let’s look at that thing!  No wonder it took you so long, jesus, that’s like a chinese finger trap!” I laughed, surveying the forest green lingerie that criss crossed Rachel’s body in all different directions.

The piece was certainly complicated, but in the end, the effect was beautiful.  It highlighted all of her assets wonderfully and made me a little jealous of how sexy she actually looked.

Rachel spun around, showing the entire piece off, and in the process, her entire body.  The straps supported her breasts, but did nothing to cover her small pink nipples, and also featured a rather large cutout on her ass, which, when she had received it, she had told me was one of the reasons she had bought it; “for easy access” she had touted. 

As Rachel twirled, I made the mistake of glancing Brian’s way.  His eyes were transfixed on me in a way they never had been before, making me feel all the more self-conscious about my skimpy attire.  

As our eyes met, he smiled a soft, gentle smile, “You look amazing,” he said softly, giving me a full head to toe once over.

“Thanks,” I replied bashfully, blushing at the compliment.

“Ok, enough flirting you two!  Mary, it’s your turn to ask, so let’s get this game going.”

I turned to face Brian, “Well, clearly you’re the target.  Truth or dare?”

Brian let out a sigh and leaned heavily on the counter, “Fuck it.  It’s going to happen at some point, might as well get it over with.  Dare.”

“Ok, now we’re talkin,” Rachel crowed.

“How mean should I be?” I asked with a laugh.

“How mean?!  Mary, I can see your clit.  Be as mean as you want!” Rachel laughed.

“Ok, should we just end this game right now?” I asked.

“Up to you,” Brian replied with a shrug.

“Ok, screw it, let’s just end it now.  Strip.  All of it,” I said nonchalantly.

Rachel leaned back against the kitchen counter and folded her arms, ready to take in the show.  I followed her lead, standing next to her as we both surveyed Brian.

A heavy sigh left him as he stepped back from the counter and pulled his t-shirt up and over his head.  While we had been friends for a few years, never had I actually seen Brian shirtless.  As his torso came into view, I was surprised by how well he hid, what turned out to be, quite the physique.  A toned stomach, defined pecs, and nice shoulders all came into view, his chest speckled with just a touch of hair.  If I was honest, I would have been happy if he had stopped right there.  However, that was not what I had asked, so on he went.  Kicking off his shoes and socks, he set them neatly against the wall next to where he stood before unbuttoning his jeans and sliding them down off his legs.  His black boxer briefs hugged his thighs while a small dot of wetness at the groin caused my heart to skip a beat.  Was that precum?  Had we turned him on enough to start leaking already?  Finally, Brian hooked his fingers under the edge of his waistband and slid his last remaining piece of clothing off.

His semi-erect cock sprang into view, and while not fully hard, it was of average length, but slightly above average girth.  It was hard to put my finger on exactly what made it so, but it was one of the most beautiful cocks I had seen.  It wasn’t overly large, but it was well proportioned, hung straight with little to no curve, and was well manicured.

Rachel had her hand covering her mouth as she chewed at a fingernail, staring intensely at Brian’s swollen member, “that’s a nice one,” she whispered so only I could hear.

“I know,” I whispered back, covering my mouth so Brian wouldn’t hear us, “It’s kind of beautiful.”

“Uh, can we stop whispering?  Little nerve racking to drop your pants and then have people whisper back and forth,” Brian said with a nervous laugh.

Rachel dropped her hand, clasping them behind her back, “Oh, sorry.  We were just saying you have a beautiful dick.”

Brian laughed, “Oh…well…thanks!” he replied, blushing, “So, game over then?  I think that pretty much gets everyone to even,” he said, clearly a little uncomfortable standing there totally naked.

“Yeah, I’m fine with calling it there,” Rachel replied, “Should we just play beer pong then to get rid of some of this beer?  We’ve made no progress at all with this game being so distracting.”

“Yeah, that’s fine.  Lets change, then we can get it set up,” I suggested.

“Change?  No!  Lets just stay like this the rest of the night!” Rachel chimed.

“What?  Why?” I asked.

“Cuz…I mean…don’t you want a little eye candy for the rest of the night?” she mumbled, nodding toward Brian and his gorgeous erection.

She had a point, and given we had all seen each other like this already, it didn’t seem too hateful of an idea, “Ok, fine.  We stay like this til bed.”

“Woohoo!  Naked beer pong!” Rachel cheered as she grabbed a stack of solo cups from the top of the refrigerator and started setting things up.

Over the next 3 hours, the three of us played countless games of beer pong with Brian winning the majority against Rachel and me.  The game accomplished the task set out, thoroughly putting a dent in the amount of beer we had remaining.  However, the games also accomplished the task of getting Rachel and I thoroughly drunk.  Brian’s state of inebriation was difficult to pin down in our own drunken stupors, however, one thing was certain, the alcohol did not seem to be impairing his ability to hold an erection, which swelled, and stood tall for all to see the majority of the evening.

Eventually, Rachel let out a yawn, stretching her arms over her head, “Ok, I’m drunk and exhausted.  I’m going to bed.  I’m so glad we stayed in tonight so it’s a short walk,” she laughed, leaning against the wall and starting to stagger her way toward the bedroom, “night you two.  This was fun.”

I stretched my arms over my head, following Rachel’s lead, “Yeah, I’m exhausted too.  Call it a night?” I asked, looking across at Brian and doing my best not to stare at his dick.

“Yeah, I’m pretty spent as well.  You care if I crash on your couch for the night instead of the 15 minute walk back to my place?” he asked.

“Of course, let me see if I have an extra blanket and pillow,” I replied heading to my room to rummage through my spare linens.

As I closed the bedroom door behind me, my phone that was tucked into the waistband of my thong buzzed.  I quickly pulled it out, wondering who would be texting me at this hour, only to see a text from Rachel.

“What the hell are you doing?  I went to bed to give the two of you some privacy!”

I stared back at the message before tapping back “What?  Why?”

“Are you serious?!  Did we just stand around in lingerie for the past 3 hours with a nude guy and his beautiful hard dick for neither one of us to get laid?!”

I laughed softly, “Uh, I guess so?”

“Ok, hear me out.  He’s hot, he’s got a nice dick, and he’s super nice and clearly not pushy given he didn’t make any major moves the past three hours.  As someone with some experience in this, I’m telling you, if you ever wanted to get your ass fucked, he’s kind of perfect for it.”

My eyes bulged as I read her text, “What?!  Tonight?!  Absolutely not.”

“Fine, your loss.  But would you be mad if I made a move?  I’ve been thinking about it since the moment he took his pants off.”

I rolled my eyes, “Knock yourself out.”

I grabbed a spare blanket and pillow and took it back out to where Brian had stretched out on the couch, now having put his boxer briefs back on, “Here you go.  If you need anything, just knock,” I said, handing him the linens.

“Thanks.  Sweet dreams!” He replied, taking the pillow and blanket and getting situated.

I returned to my room, shed my underwear and bra and climbed into bed nude.  I lay there quietly, thinking about the text that Rachel had sent.  The more I thought about it, the more I became turned on by the idea of Brian’s cock sliding between my cheeks.  As I lay there daydreaming, my hand drifted to my clit and I began slowly circling my sensitive nub.  

It wasn’t long before I heard Rachel’s door open and the soft sound of her footsteps making their way out to where Brian lay.  Suddenly I felt jealous.  She was going to get what I wanted, and yet, I had actively turned it down and had no reason to be mad at her.  I had even given her my permission to take it!

It didn’t take long for the soft sounds of Brian and Rachel making out to pierce the otherwise silent apartment, and then the sounds of rhythmic thrusting and muffled moans to reach me as well.  My finger continued in tight circles on and over my clit, the sounds of Rachel taking Brian’s cock an unforeseen turn on.  My eyes closed and I imagined what they looked like.  What position were they doing it in?  Was Rachel actually taking it in the ass?  What did that really feel like?  I had to know.

I swung my feet out of bed, stopping to reach into my bedside table and grab my bottle of lube.  Ever so quietly, I eased my door open and tiptoed out of my room toward the kitchen and living room.  Suddenly, the thrusting stopped, the moans went silent.

“Mary?” Rachel’s voice cooed in the silence from just around the corner.

My heart stopped, they had heard me.  But what was my plan?  I had come out here for one reason and I wasn’t going to satisfy that reason without them knowing I was here.

I swallowed hard, “Yeah?” I replied softly.

I could almost hear Rachel’s smile in the dark, “Want a turn once I’m done?” she asked.

“Maybe?” My voice shook with anxiety.

“Yes you do.  Come here and stop being creepy and standing around the corner,” she commanded.

I finally gathered the courage and stepped out into view.  Brian was sitting upright in the middle of the couch as Rachel straddled him.  I took the sight in and felt myself flush with both embarrassment and arousal.

“Mmm, perfect!  You brought lube!” Rachel chirped, “Here, let me slide off a sec.  Can you squirt some of that on him?” she asked, “That’ll work better than the spit I was using.”

I slowly walked around and crouched down, flipping the cap up on the bottle as I watched the length of Brian’s cock slowly slide from the depths of Rachel’s ass.  I gave a quick squeeze, watching a healthy amount of lube coat the head of his member.  Rachel reached beneath her and slowly stroked his length, coating it in the slick liquid before repositioning it at her entrance and lowering herself back down onto it.

“Mmmm fuck that’s better,” she groaned, not trying to be quiet any more.

I sat back on the floor, taking in the sight of my roommate enthusiastically taking a cock up her ass again and again.  Brian’s soft grunts of delight as she slammed back down his length matched Rachel’s moans of ecstacy.

“Oh my god, so good,” she gasped, “Your dick is fucking perfect.” she panted through labored breathing, “C’mon, talk to me, we don’t have to be quiet anymore.”

The version of Brian that suddenly appeared to me was unlike any version I had seen before.  He had always been kind and gentle, understanding and easy going, never the type to demean or degrade in any way.  However, in that moment, he was far more…primal.

He thrust up into Rachel, pounding her ass hard and fast as he gripped a fist full of her hair, pulling her head back to expose her neck as he kissed and licked the edge of her jaw before dropping lower to suck at her erect nipples.

“Fuck your ass feels good,” he growled, “and I know you love to have it stuffed don’t you?”

“Yes sir,” Rachel whimpered, mewling with pleasure, “I love it so much.”

“Mmmm, take it all like a good butt slut,” he groaned, pounding into her with a new found ferocity.

“Oh my god, I’m ganna cum, I’m ganna cum,” Rachel stammered a short while later, her hands gripping the back of the couch tightly as her mouth fell open silently, her eyes slammed shut.

“That’s it, let that tight little asshole cum on my cock,” Brian whispered softly.

Rachel let out a long cry of passion as her knees clamped around Brian’s legs, her whole body tensing in a moment of bliss as his cock pistoned in and out of her twitching asshole.  As the waves of pleasure subsided, Brian’s thrusting slowed to a snail’s pace, gliding in and out with long, methodical strokes.  The entire spectacle was the hottest thing I had ever seen in my life and I was absolutely transfixed.

Finally, Rachel sat back, taking the whole of Brian’s length inside her, her eyes opening to stare into his.  The moment their eyes met, Rachel closed the distance between them, kissing him hard and passionately before breaking it off and leaning back again.

“Holy fuck that was good.  Can we keep him?” Rachel laughed, turning to look over her shoulder at me.

As she looked at me on the floor, a smile spread over her face as she glanced down between my legs, clearly seeing the sheen of my arousal that had coated my inner thighs. 

She turned back to Brian, giving him a soft peck again, “How close are you to cumming?” she asked.

He shrugged, “the alcohol is certainly helping to numb the sensation just a bit, so I’ve got a fair bit left in me,” he said confidently. 

“Perfect,” Rachel replied, slowly lifting herself off of his length, “Mary, I think it’s your turn.”

Any nerves I had felt when I came from my room were gone.  Watching Rachel had solidified that I had made the correct decision.  I wanted this.

“Should I do it the same way you did?” I asked Rachel, hoping she would have some advice for my first time.

“Probably not for your first time.  I’d go doggy for the first time,” she coached.

Following her advice, I climbed onto the sofa next to where Brian sat and positioned myself on all fours with my elbows resting on the sofa arm.

“You’re going to need a few fingers first right?” Rachel asked.

“No, just…just give it to me,” I replied, almost desperate, “I used my plugs earlier today so I should be ok.”

Rachel smirked, “Oh, so there’s multiple plugs huh?”

I was beyond hiding anything at this point, “there’s 4 of them,” I confessed.

“Ok, well give the little anal fiend what she wants then!” Rachel said, kneeling next to me, her hand softly caressing my ass.

My heart pounded in my chest with anticipation as I felt Brian position himself behind me.  The head of his cock rest against my uncharted hole.  The click of the lube broke the silence and the cool sensation hit me as he coated himself and me in a healthy amount.  Then it began.

Slowly the pressure built.  More and more I stretched as he pressed against my defenses until I wasn’t sure I would be able to take it.  But then, suddenly, he was in.  In a fluid motion I felt my tight little hole yield and his cock slide inside me for the first time.

“Oh my god,” I gasped, “That’s- that’s so big.”

Rachel laughed, “Honey, you’ve only got about an inch and a half.  You haven’t felt anything yet.”

Just as I was about to respond, another inch slid inside me, my mouth falling open, my eyes bulging.  There was no way I was going to be able to take the whole thing.  It just didn’t seem possible.  Slowly but surely, Brian worked his cock up my ass with patience and care, until finally, I felt his hips press against me.

“Good girl,” he whispered softly, “how’s it feel?”

“Enormous,” I groaned, “but amazing.”

Slowly he began to thrust, easing his length out and then penetrating me again.  Bit by bit he increased in speed until I was taking his cock with ease.  I moaned and panted, my body on fire with a level of arousal I had never experienced before.

Rachel gave my ass a firm smack as she kissed my cheek, “That a girl.  Now you’re really taking it.”

Brian’s hands fell to my hips, pulling me back to meet his thrusts, to which I was happy to oblige.  Again and again I threw myself back onto him, reveling in the sensation of having my ass so full.  Deep inside me a tension began to build, it wasn’t like orgasms I had had before.  This was deeper, more concentrated, more intense.

“Harder,” I groaned, letting myself completely sink into the experience.

Brian doubled his pace, fucking me hard and fast, my body happy to be used for his pleasure.  His fingers gripped the cheeks of my ass, spanking me and spreading me open for his pistoning cock.

“I’m ganna cum soon,” he grunted between thrusts.

“Yes…I want it,” I replied, eager for the new experience.

Again and again Brian’s cock split me open until finally, with a deep guttural groan, he slammed his length deep into me.  A radiant warmth erupted inside as I felt his cock twitch and spasm, unloading his cum in my ass.  I moaned with satisfaction, a smile spreading over my face as I had taken the first, of what was sure to be many ass fuckings in my life. 

Source: reddit.com/r/Erotica/comments/ylcfv6/f21_first_anal_experience