Alex's First Date

My name is Alex. My first sexual experienced was unusual in many ways. First of all I was already 21 years old, never had sex and never even kissed a girl. I was fit and looked good, but for one reason or another I never felt comfortable enough with a girl to go on a date. As I got older I got more confident and finally one day I downloaded a dating app. I lived in the dorms at a college so the app was filled with girls.

After a few days of trying at it I finally matched with someone and started up a good conversation. It was with a girl named Ash. She was like my dream girl. She was 19, had short brown hair, and a flat chest. She was very fit and somewhat muscular from being on the rugby team, and she was very tall. I'm not too short myself, I'm 5'8", but she was a solid 6'2". I didn't know any girl that tall, I found it attractive.

We started talking a lot about music and movies, we had similar taste and were getting a long well. One day after maybe four days of talking about mundane things and interests, she out of the blue she suggested we meet up sometime. It was a curt but I was so into her that I didn't even think about it. I suggested we meet in at coffee shop but she said we should just hang at my place. I explained how it's kind of awkward since I have 3 roommates total in the 2 room of our dorm apartment and the walls are kind of thin so any conversation we had they could be able to hear. Ash just persisted and said "No I think your place is fine :)." So we planned to meet up the next night.

My Dorm's apartment is set up so that there's two bedrooms and two people per room. Jordan's always having girls over and loudly fucking while I have wait it out in the living room or in the library. The girls he hooks up with always moan so loud that I can hardly get any work done at the apartment, and more often than not they fuck all night, forcing me to sleep on the couch to the sounds of their fucking. My other two roommates Logan and Ryan did pretty well themselves, often each fucking a girl at the same time in their room. All of my roommates seemed sex crazed while I never once brought a girl over before.

Since I never had a girl over, when I brought up to Jordan that I'd need to the room to myself night he laughed out loud.

"What?? Is little Alex really bringing a girl over?!" he asked loudly.

"Well it's just a chill hangout, nothing like you guys."

"Don't be so down on yourself, I bet you guys will fuck right away, and if not I'll help out!" Jordan again laughed in my face.

Although his comments for the next day were pretty demeaning, he agreed to let me have the room, and as the next day came around I heard a knock at the door. I opened the front door and there was Ash. She was a goddess. I had to turn my head up almost straight up to make eye contact. She was wearing a skin tight crop top band t-shirt that showed off her abs, and short shorts that made almost all of her legs visible. I wasn't able to see from the photos on the app but she had a fat ass, and her short shorts only accentuated it. She had a strong jaw line which perfectly framed her beautiful big eyes.

While I was nervous and already starting to blush, Ash walked right pasted me and started to check out the apartment.

"Wow this place is pretty chill." She said.

Her confidence only made me more embarrassed and all I was able to mutter out was a meek "Thanks."

Ash walked into the living room and right away my roommates stopped the game to start gawking at Ash.

"HOLY SHIT! Alex who is this fine ass you brought here!" Logan yelled.

Ryan got up and stood next to ash "Damn I'm just barely taller than her. Alex you better be packing something big or she's gonna leave disappointed!"

Ash laughed "Wow you guys sure seem fun."

I ran into the room at the verge of a heart attack and tried to pull Ash by the hand out of the room out of embarrassment but she pulled back and was way stronger than me. Just then her and Jordan's eye met and I could tell they knew each other.

"Ash, what are you doing on a date with this pipsqueak?" Jordan said confidently

"Oh Jordan, wow it's been forever. How are you?" Ash said smiling

"Much better now that I see that fat ass again! Hahaha!"

Obviously I could tell they fucked before, and if it was anything like what I've heard in the past, I'm sure Ash remembered it well. I was uncomfortable so I pulled harder and managed to get Ash's attention away from her past fuck and had her follow me to my room.

"Sorry guys talk to you later!" I yelled.

Once in my room was so relived not to have to deal with the situation. Ash on the other hand found my humiliate likable.

"You're pretty cute you know. I like how embarrassed you are. I didn't think you'd be so short from your profile, but that's okay I like shorter guys, it's easier to manhandle them."

Standing side by side in my small bedroom the height difference was clearer than ever. Ash put her hand on the wall over my head. Standing straight over me I realized that I might not have known what I was in for with this date.

"Hey so do you wanna maybe sit down and listen to some music or something, we could watch a movie?" I said.

Ash looked at my with a devilish grin and said "I have a little something more exciting in mind."

I really didn't know what she meant but she made it abundantly clear as she bent down and literally picked me up off the floor and threw me over onto my bed. I had never felt so unmasculine but it was the hottest thing I've ever felt.

Ash crawled onto the bed and got close to me, pressing her mouth against my ear she asked "Do you want to kiss me? Do you want me to make you feel good?"

I was blushing bright red "Oh uhh I guess whatever you want to do."

"Whatever I want do? Are you sure you're okay with that?"

"Sure whatever."

Ash then placed her hand on my dick and grabbed it hard. "Does baby like that?"

I was as hard as a rock, the blood was leaving my head quickly and all I could think about was how good it was "Yes that feels amazing."

Ash then out of nowhere, with her free hand, smacked me across the face with her full force leaving a huge read hand mark. I screamed because it hurt so much and couldn't help but notice that she was squeezing my dick harder than before.

"CALL ME MOMMY YOU LITTLE BRAT!" She scream at me

I was so caught off guard I had no idea what to think. I said "Yes Mommy whatever you want, but please could you not be so loud these walls are so thin that I'm sure my roommates can hear you"

Ash then slapped me across the face again and said "I don't give a fuck brat!"

I was stuck in a place of feeling the greatest sexual pleasure of my life from something as simple as a hand over my jeans and feeling great pain from being slapped twice across the face by this amazing goddess who had all the power over me.

Ash seeing how much control she had over me realized she really was free to do whatever she wanted to me. She stood me up and starting talking off my clothes. I was completely naked standing in front of her with all of her clothes still on. As she pulled down my underwear she saw my dick. It was hard and precumming from her touching it, it was the first time I was about to show a girl my dick so whether or not she had hit me or wanted me to call her mommy I was proud to show it off. But to my surprise when she revealed me throbbing cock instead of being in awe of it she immediately fell down laughing at it!

"Oh my god, I realize you're short but what is that thing?! I've never see a dick so small! It's hardly a dick at all, I couldn't even put that in my pussy if I tried! What a waste of time for me to come all the way over here just to see this."

I had no idea my dick was small. I was a solid 2 and a half inches and always felt like it got the job done, plus I've read articles saying that girls prefer smaller dicks, but that couldn't have been further from the truth. As Ash was rolling around laughing about my small dick I became acutely aware of the lack of video game sound coming from the living room, I think I even heard some laughing coming from out there.

Ash composed herself and looked me straight in the eyes "Well baby boy, you've done bad and need to be punished."

Ash then picked me up again and laid me on her lap with my ass in the air. She put my tiny penis in between her knees and squeezed them together crushing my dick, I yelled and right as I did she spanked my ass. Again and again she spanked my ass and each time she did my dick would feel the pain of being stretched in between her knees and I flailed around in pain.

Ash was laughing and seemed to love being able to inflict pain on me. "You told me you're a virgin, is that true?" She asked as she spanked me again.

"Yes it's true!" I yell in pain

She spanked me harder "Who are you talking to you little shit!!"

"Yes it's true Mommy!" I screamed.

"It makes since with a dick like that, I doubt you even could have sex. I bet each of your roommates have bigger dicks, you're pathetic." As she said that I heard a loud "Fuck yeah we do!" from the living room along with tons of laughter. It was obvious they could hear every word spoken, I had never been so humiliated.

"Have you kissed a girl before?" She asked.

"No I haven't, I haven't done anything with a girl, this is my first time doing anything."

She giggled "Well lucky you, because I'm going to help you lose your virginity today!"

I started to think that this torture I was being put through might come to a close but right as I thought that I started to feel a pressure on my ass. Ash forcefully inserted her middle finger right into my asshole, taking my asshole virginity. I had never put anything in there, I was so tight and her finger alone was causing me pain. She started moving her finger back and forth and involuntarily I started to moan.

"Oh does baby like that?"

"Yes Mommy."

She then inserted another finger and started working her hand faster. She had a grip on me like a bowling ball and I could feel her slamming my prostate with each thrust. I had never felt such sexual pleasure in my life, even with all the pain and the fact that I was being fucked in the ass.

"Does baby like having his little boy pussy treated like this" She asked loudly

"Yes Mommy, my boy pussy feels great."

"Say you want Mommy to make you cum from your boy pussy."

As Ash said that she slammed my prostate hard causing me to yelp "I want Mommy to make me cum from my boy pussy!!"

At this point we were being so loud my roommates couldn't have been focusing on anything other than the noises from my room, and as I yell "Boy Pussy" I heard an especially loud round of laughter and Logan yell "Be careful with my roommate's pussy!" and more laughter.

Ash leaned down and whispered in my ear "Cum for me baby. Let it out for Mommy."

Uncontrollably, at her will I came harder than I ever had before. I blew all over the ground and her converse shoes. and just as I did I knew that was just another part of her plan.

Ash grinned and said "It looks like baby made a mess, well you're going to have to clean it up"

With her two fingers still in my asshole she pushed me off her lap and onto the ground. I felt like a dog with a leash, and the post cum clarity was starting to hit me full force. All of a sudden I realized that I had just had my first sexual experience and it was in the strangest situation possible. This younger girl had so much physical and mental control over me and I could hear my roommates still laughing from the other room. This was such a disgusting, humiliating place to be in and the last thing I wanted to do was anything sexual, but Ash just grabbed my head like a dog who pissed on the floor, and pushed my face into her cum covered shoes.

"Lick up that cummy messy you little bitch!" she yelled, definitely loud enough for my roommates to hear

With my own cum on my face I tried to stop what was happening "Please Ash could we take a break, this has gone a little far"

Ash then with all her might dug her fingers into my asshole, her fingers where so long and slender. She manged to push them so deep inside of me I couldn't believe the pain and sexual pleasure I was feeling. I never imagined I could fit something so deep in my asshole.

"YOU'RE GOING TO DO WHAT I ASK, AND CALL ME MOMMY YOU SHIT HEAD!"

I had never felt the kind of pain that being fucked hard in the ass brings, but as soon as she pushed harder I did exactly as she said. I started licking up my gross, dirty cum off her shoes. It was lick and tasted horrible, and I had never cum even close to this much before. There was so much to lick up. What made it worse was the absolutely horrible stench coming from her feet. She must have had a rugby practice before coming over because I had never smelled such bad feel that the stench was coming through the shoes.

I was in the worst position imaginable. On all fours, with Ash's long, slender fingers deep in my ass, with my face down licking my own cum up off her feet. I was gulping up one lick full of cum after the other when all of sudden I saw a flash. Ash had taken a picture of me!

I turned up in horror and yelled "Oh no please Mommy, please don't show that to anyone Mommy, please I'm begging you!"

"I can show this to anyone I want."

"Oh please Mommy, anything please anything, just please don't show that to anyone."

Ash then seemed to lighten up a bit "Okay baby, I'll keep this to myself. I promise."

It was easily the most embarrassing and damaging photo that had every been taken of me and I was completely frighten of what would happened if that got out, but her promise eased me worry. Even though she's a sadistic woman, I trusted her to keep it to herself. As I finished licking up the last of the cum, Ash finally pulled her long fingers out of my ass, but then made it even worse.

"You're not done cleaning bitch boy." She said and she shoved her fingers into my mouth for me to lick clean. They tasted like shit. This was the grossest most humiliating thing I've ever done before. Ash just laughed as my face twisted in pain from the filth I was dealing with.

"Wow you're Mommy's little helper, you clean me up so well. How about you help me a little more." She then started taking off her shoes. I realized this was just going to get worse since the thing Ash seemed to get off to the most was my own pain.

I was still on all fours with my face next to her feet, and as Ash took her shoes off the stench amplified. The smell was almost unbearable, like rotten eggs. She loved seeing me recoil at the putrid stench. She pulled off her right sock and started stretching her toes out. She had the biggest feet I had ever seen a woman have, besides the stench they also were visibly dirty. Covered in dirt and filth with lint between the toes.

"Isn't it magnificent?" She asked.

"Yes Mommy, I love your huge feet."

"Does baby like helping Mommy clean?"

"Yes Mommy, what ever you wish."

Ash looked so happy at my disgust and seemed even happier to say "Okay Bitch Boy time to clean this foot."

I slowly inched forward with my tongue out and eyes closed but unexpectedly Ash jammed her foot straight into my mouth. Suddenly I was gagging on her toes and the horrible stench was filling all my senses. My eyes were watering with how deep she managed to lodge her foot into my mouth. She then stood up with the other foot and was towering over me. She was pumping her foot in and out of my mouth as I tried to lick in between her toes, all I could sense was smell.

Right at one of the most humiliating moments I heard the sound of the door opening. It was all three of my roommates standing there, laughing their asses off at the sight of a fully clothed goddess standing over me with her foot in my mouth while I laid all fours on the floor and my gaping asshole in the air. They all were laughing and taking pictures with their phones out.

"God damn, you two are having a party in here!" Logan yelled.

"It looks like you need some help in here Alex, hope you don't mind." Jordan said with a smile.

Ash pulled her foot from my mouth and I could finally breathe again. She put her hands on her hips and look at my roommates. "You boys think you can just walk in here and do what you want to me? Fuck no. But maybe you can help me out a little. Come over here and line up by the bed." As they started to walk over Ash picked me up and stood me up straight with my little, flaccid penis out in the open.

Now the guys were really starting to laugh. They started taking pictures of my tiny dick and talking about how they've never seen one that small. The line of boys went Ryan on the far Right, then Logan, Jordan, and finally Me. Jordan was the tallest in the room. He was about 6'6", although even the shortest of my three roommates, Ryan, was still taller than Ash. I was by a huge margin the shortest in the room, completely naked with a tiny flaccid penis, I felt like a woman.

With us all lined up, she looked me in the eyes and said "This little virgin needs to learn a thing or two about sex and what real men are like so I was hoping the three of you could help."

"I don't know Mommy, I think this is a bad idea." I said

She slapped me and yelled "Shut up you pathetic little bitch boy! You need to learn what real cocks look like or you'll never understand how worthless you are!"

Ash got down onto her knees and then started undoing Ryan's pants. She pulled down his underwear, and out flopped a thick flaccid penis. She started stroking it to get it to grow and as it did it revealed itself to be at least three times the size of mine.

Ash said "Well look here, nice length and thickness, his balls are even of a good size. This is probably about six and a half inches." Ryan cheered and fist bumped Logan.

She then scooted over to Logan and undid his pants As she pulled down his underwear, his penis came out swinging and knock Ash in the face. She playfully laughed and started stroking it. She wasn't shy at all to be stroking multiple dicks with four men watching her. It was like any other activity for her, like this was her job, like she'd done it thousands of times before. She used two hands this time and when he was finally erect Ash proclaimed "Wow! Nice this must be almost eight inches!" Logan raised his fists to the sky and Ryan was annoyed.

Ash finally moved over to Jordan and looked straight up into his eyes. Jordan smiled back and said "I think you're going to be happy."

She pulled down his pants and underwear and to everyone's surprise, not only was he unquestionably the biggest cock in the room but he was full erect already and as Ash pulled down his pants his hard cock bounced up slapping her in the face and bouncing into her wide open mouth.

Ash pulled his gigantic cock out of her mouth and spit on the ground "Oh fuck, that smelled horrible! I see you still don't like to wash your cock. The smell from your balls is filling the room!" And she was right. For as long as me and Jordan have been roommates I've had to smell his balls and ass. After he fucks it's the worst. All my clothes smell like his balls.

"Get down here and check this out." Ash yelled as she pulled me down by my arm. Suddenly I was face to face to my roommate's throbbing cock. Ash had to use two hands to even prob it up straight. "Wow Jordan, you've grown. This is probably nine, or god, maybe even ten inches. Take a good look at this Alex, he's five times as big as your little penis is. Jordan could use this as a bat and beat your little clit black and blue."

Ash reached down and griped my balls, squeezing so hard I started to tear up. She whispered "You will never please a woman with this."