Sharing Anna Pt. 01

I was approaching 35, still single since I'm not big on commitment. Tinder started to become a thing and I met new women regularly. I do enjoy dating, but I mostly just wanted to find a girl that would fuck me without being overbearing. I had to find new women regularly so they wouldn't get too attached. Plus, women around my age all get pretty impatient, so I looked for younger girls that weren't so pushy.

One day I met Anna, she was 24 years old, a petite young girl. I didn't fully appreciate how petite she was until I met her in person the next day. I walked into a bar where we agreed to meet after work, she had long brown straight hair, was mixed Asian and had this sexy young innocent look. Her breasts were about a C cup and as she spoke I imagined how perky they would be. I could easily imagine them bouncing in my face while she rides me.

Her legs were nice and long, but she wasn't too tall, she was average height. But when she got up I saw her plump ass, outlined by her tight pants. For an Asian, she had a nice full ass, but it wasn't too big. I knew I wanted to see her again, since I would happily eat her pussy.

As we chatted I found out she had an ex boyfriend and a bit more about her boring past. I told her a little bit about me but all I really thought about was how long until she would let me fuck her. I put on the charm and made it clear how eager I was to get her into bed. She seemed shy but not entirely insulted, so I knew she was thinking about it.

After a few days I asked her out to dinner, still working to charm her. I knew I'd have to keep up appearances to keep her keen, she agreed and a couple of days later we met for dinner. I took her to a wine bar where we had dinner and a bit of a laugh, but since I had caught an uber there, I let her drop me back to my apartment. Of course, I invited her up for a tea and to see my place which she agreed to.

I knew she was low key wanting me all over her, otherwise she wouldn't have agreed to come up. So we sat on the couch and I stroke her hair since women like it. I moved in to kiss her and gently touch her leg, testing how far she would go.

She wiggled in the couch and I knew she had a little tingle in between her sexy legs.

My cock grew hard from her wiggle, so I decided to try for more. I parted her lips with my tongue and kissed her, then suggested she come and lay closer to me under the blanket on the couch.

She did, and I knew I was in. I rubbed her legs and buried my tongue into her little mouth. Moving my hands over her tight pants and grabbing at the side of her ass, acting shy so she would come to me. She moved her hips towards me to get me to grab her ass, so I took the opportunity. I grabbed her and squeezed her cheeks firmly, breathing out heavily in eagerness to rub my cock against her. My cock was rock hard, I just needed to get it out of my jeans and between her lips. I wasn't particularly picky about which lips though.

I moved my hands in between her thighs and she parted her legs a bit, so I moved my hands over her mound and rubbed her firmly. She moaned softly and that was permission to keep going.

I slipped my hands into her pants and straight under her panties, so I could rub her in between her slit. I felt her lace panties graze at the back of my hand, and I found a nice bold pussy waiting for me. I let out a moan as I felt her soft shaved lips and ran my cold fingers into her slit to rub her and feel how wet she was.

She bucked her hips at me more and instinctually I pushed my finger into her. I'll never forget how I could feel the walls of her pussy, snug around my one single finger.

I have quite a thick cock, and precum started pooling at my circumsized tip with anticipation of this tight, soft, young juicy hole trying to take me. I commented as I fingered her, "Mmm, wow Anna - you're very tight."

She giggled coyly, but I was obsessed with how tight she was.

"Ohhh fuck Anna, I don't know if you can even take two fingers," I said.

I asked her to pull down her top for me, while I removed my finger and inserted my middle finger to get it wet. She freed her young perfects breasts, her hard nipples stood perfectly positioned. Her skin was flawless, and I took her nipples straight into my mouth, flicking them with my tongue. Making her pussy even wetter and juicier for me.

I pulled down her pants and parted her legs. Since she seemed a bit shy, I left her panties on and pulled them to the side so I could get my two coated fingers in. I had to feel this tightness to mentally prepare myself for how I would hold back when I got my cock in there.

I circled the entrance to her hole with my fingers as I licked her nipples, I looked up to see her face as I started to push my two fingers in. They didn't glide in easily, it was tight, my fingers were being squeezed together by her hole even with her lubrication. Her jaw opened and she moaned from the pleasure of my fingers. I curled my fingers in her and tried to move them in and out, but her pussy was gripping onto my fingers, making it hard to do that.

I took her cute titts out of my mouth and removed my fingers from her hole and said, "Your tiny pussy is hurting my fingers, you're going to need to be very wet for anything else."

I got up to lick her pussy, and pulled off her panties. I desperately wanted to taste her and I needed to make sure she was soaked.

I held her pussy lips apart and revealed her pink, fresh, young, very tight hole. I had hit the jackpot, this was going to be a fuck I would remember.

I panted as I looked at it and dived my tongue into her, tasting her sweet juices. She was so clean and fresh, her juices were sweet as well, she had the most delicious pussy I've ever tasted.

She moaned while I lapped her up like a man possessed, I looked up to watch her squirm on my tongue and told her, "Touch your breasts for me little girl."

She grabbed onto her breasts and bucked her hips at me, while I happily used my tongue to pleasure her. I became so hard that I desperately wanted to fuck her before I exploded in my pants. My cock was twitching and completely solid, ready to be buried into this ripe young girl.

I got up and released my cock from my pants, I guided her hand to my shaft so she could jerk me while I got into position. I could see the look of surprise on her face that my cock was so large.

I looked down at her hand around my cock, I had a lot more precum than usual. But I panicked for a moment thinking she might be a virgin and I hadn't asked. I kissed her and asked her, "You're not a virgin are you?".

She responded quietly, "No."

I was glad because I would have felt bad that I couldn't help but take this young girl on my couch. I didn't really want to deal with the fall out of that, even though I probably still would have done it because, who could resist this tiny cunt.

I responded, "Good," and positioned myself at her entrance.

I started to push into her which was no easy mission, her pussy was resisting the head of my thick cock. I moaned from pleasure as her walls squeezed around me. I tried to pull out slightly to ease back in, but her hole grasped onto me tightly and moved with me rather than letting my cock move freely inside her.

I let out a moan of extreme pleasure, "Ahh! Fuck!"

She asked me concerned, "Is it OK?"

Trying not to cum prematurely from her extremely tight pussy, I relaxed my frown and responded, "Is it OK!? It's very fucking OK. It's just hard not to blow!"

I was only one third if the way in and I knew that I needed to be more forceful to get in her. I told her urgently, "You need to spread your legs more please!"

She spread her legs more which made a small difference, and I took each of her ass cheeks into my hands to spread them apart. As I did I started firmly forcing myself into her hole to take me. My cock pulled which hurt but felt pleasurable at the same time, I was OK with a bit of pain for this joyous tight squeeze.

Anna was moaning and panting heavily as she tried to take me, "Ahh! Trent! You're stretching me!" she cried in a pleasurable tone.

I grunted as I made the rest of my way in, "Ohhh! Anna! I know! your pussy is squeezing my cock!"

I finally managed to get all the way in and had to pause to let her loosen her grip around me.

"How does that feel?" I asked her.

Her face reflected extreme pleasure, "I feel, so... full," she responded.

Her hole relaxed around me, I let out a sigh and announced, "Ready?"

I started firmly but slowly moving in and out of her before she could answer. She moaned and panted heavily.

I leaned into her petite body to hold myself up and stay deep inside her, trying to hold back exploding in her.

I commented, "Ahhh! I should have worn a condom so I can hold back," as I stroked the inside of her tight pussy.

My cock swelled and throbbed as I wanted to release my load. She must have felt it because she started to moan even louder, and with more desperation.

I decided I couldn't fuck her roughly and wait for her to orgasm because I would cum after a few thrusts if I tried. So I fucked her slowly for a couple of minutes, but couldn't hold back any more to wait.

I announced to her, "I can't hold back, where do you want it?" as I started to thrust into her knowing I was about to blow.

"Quick!" I hurried her urgently.

She moaned and wrapped her legs around my waist, "Cum inside me!" she begged. Her legs were shaking while she used them to pull me deep into her.

I thrust into her another two or three times and responded, "Yes! Ahhh! good little girl!" just before I felt cum shoot up my shaft and pause, ready to squirt out hard.

Half a second before I poured my load in her, she tensed and screamed, "Ahhh! I'm cumming! Don't stop! Uhh!"

As she said that, my cock released a powerful shot of cum in her. I announced back through my grunting, barely able to speak, "Good! So am I!" as I made my best efforts to keep ramming my shooting cock into her tight pulsating hole like she asked.

I came extremely hard and collapsed onto her little body, waiting for my swollen shaft to deflate so I could exit her.

As my cock settled down I told her, "I'm not exaggerating, your pussy is the smallest I've ever felt!"

She giggled and responded, "Maybe you can make it bigger for me, I've never felt so full."

I was finally able to remove myself from her gripping hole and responded, "I'm more than happy to take care of that. I would love to stretch you out, little girl."

Not long after, she left to go home. I was exhausted and my balls were completely drained. I had the best sleep, and the next day I woke up rock hard thinking about it.

I tugged at my cock which was a bit sensative from the tight friction, to blow my load and prepare for the day. I went to work and messaged my mate Mike to tell him about this unbelievably tight pussy I found.

Mike thought I was being dramatic but said it was hot that she had asked me to stretch her pussy out for her. For some reason, it bothered me that Mike didn't believe it.

Mike is also my go to mate to help me fuck girls that are keen on taking two cocks. I love watching a girl get fucked doggy while sucking on a cock cock at the other end. So I also knew that Mike has a long thick cock. The women always left with wobbly legs after Mike and I pleasured them.

At first I was torn between keeping this innocent young slut to myself. But I also really wanted Mike to experience what I just did.

I said to Mike, "Mate, you have to try her to know what I mean. When you prematurely ejaculate, you'll be jealous of what I've found."

I had to think of a way to get this girl to share her perfect cunt. She was obviously young and a bit shy, so I didn't want to scare her off by being too direct. Instead I invited her around to my place for drinks with friends in the hopes that I could make this happen.

She agreed, probably getting excited she was going to meet a friend of mine, probably thinking that this was some sort of relationship thing. I didn't care, I just wanted to see if I could make this happen.

At the end of the week she came over for the drinks. Mike was there and he knew that my intent was to share her, but I told him she was a bit shy so he shouldn't expect it.

We talked and had a couple of drinks and I started to warm her up, flirting with her and giving her a little grope when Mike wasn't looking.

I whispered to her, "You know my friend Mike has a big cock, and I wouldn't be jealous if you tried it".

She looked surprised but I knew I could just say I was joking to get her horny if it went badly.

She responded, "What do you mean?" in a shy tone.

I sighed and put my hand high on her thigh and I continued, "You're a young girl who might want to explore and I personally find that very sexy - no one will force you have to of course, just an idea."

I let her think about it, but I could see she was looking at Mike differently by now, wondering her eyes to his crotch, thinking about letting herself loose. He could see it too and commented to her that she was really gorgeous and fun to make her feel good.

Mike went to get us some drinks from the kitchen and I gave her a little cheeky rub in between her legs. She seemed hornier and enjoying it so I probed more, "What's on your mind?"

She responded, "How would it work with Mike?"

I smirked in excitement and said "However you want... What would you want?"

She answered, "Well, I don't want to take two guys at one time. But he's kind of sexy and I would let him, you know...do me."

I paused, thinking about the best way to handle it. Then I responded, "That's OK, I don't need to be there."

She thought about it and said, "But I don't know him and I don't want to be left entirely alone."

I offered more solutions, "that's OK too, you can do it here and I'll wait for you or come with you and just watch - whatever you want."

I knew I was successfully convincing her as she probed more, "So you would wait for me or watch your friend sleep with me?"

"Yeah babe, I want you to be comfortable," I said.

"And you would be OK with that?" she asked.

"Of course, what do you mean?" I asked back.

"Well, you wouldn't be put off me?" she asked.

"No! Fuck no. If you're asking if I'd still go there with you, the answer is a solid yes," I reassured her.

She paused and thought about it before saying, "OK, I think I would do it."

Mike came back and I nodded at him when she wasn't looking, and took a sip of my drink, confirming that she was in.

I said, "Mike, pass me the remote," so he would need to lean over Anna to deliver it and would have an excuse to get closer to her.

I offered them a blanket while they sat, but only one to share.

Mike started making his moves, flirting with her and finding excuses to touch her. I heard him whisper that she had gorgeous legs, and when she looked flattered, I saw his hand move under the blanket to her thighs.

I excused myself saying I had to make a call on the balcony and intentionally took a long time. When I got back she and Mike were in my bed, under the sheets. They left the door open enough for me to see half the room, but as I stood at the door I could see basically everything.

I heard Mike say, "Don't be shy, you can grab it," and within seconds she must have been jerking his cock because I heard him moan lightly to encourage her.

I heard him ask her, "Would you like to put it in your little mouth?"

I heard them reshuffle and soon listened to her slurping on his cock under the blanket.

Mike continued, "Take off your pants..."

I heard her moving to take her pants off before returning to slurp on his cock again.

"Mmm you do that so well Anna, it feels really good, keep going, Ohhh yeah! Good girl," Mike encouraged her.

Eventually he stopped her and said, "Come up here"

She emerged from under the blanket, hovering her snatch above his waist.

He lifted her top up, and pulled down her bra, taking her titts into his hands and mouth. He put his spare hand around her waist and guided her to grind along his shlong.

He moaned for her, "Ohh Anna, your shaved pussy is gorgeous! Come here!"

His hand disappeared, probably to hold his cock up. He quietly said, "Get on."

Within a few seconds I heard him moan out loud, "Ohh! Fuck!"

He sounded just like me trying to get into her.

"Wait! Ohhh! OK go," he continued.

All I heard as I peeked through the door was Mike feeling exactly what I told him.

"Mmmm! Uhhh! That's fucking tight!"

"Wait, wait! OHHH! AHHHH! YEP, Get it in you Anna."

"FUCK! I don't know if you can take it all!"

I heard Anna moan, "It's nearly in, I'm sorry!"

"UHHHH! Don't be sorry little girl. I love it! OHHHH wait, I might put a condom on so I last..... OHHH nope, she's not letting go of me! OK fuck it! Bareback it is!" he said.

I listened to Mike continue, "Ohhhh! Go, go... AHHHHH Yes! Wow! I can't believe you managed to take it all the way in!"

She rocked on his hips, "You're so deep! Uhhh!"

He responded, "AHHH YEP! RIDE ME ANNA! Ride me with your tight little pussy."

She bounced on his cock in pure bliss. I could see from the crack of the door, his cock was buried balls deep in her. The skin on his cock was being pulled down when she landed on him over and over.

He said, "This is a bad position! Are you on birth control? I'll blow with nowhere to go."

She replied, "No, but it's OK."

I was surprised, I didn't even ask her last week, but I came in her since she said I could. And now she was saying Mike could too!

Mike moaned, "OHHH! That young naughty pussy! You're going to make me cum, seriously I should pull out!"

She didn't stop, she kept bouncing on him at the same pace, her titts jiggling in his face, "It's OK, I love being cummed in! I love the feeling inside me! Cum in me Mike, please?"

He stopped her from being able to ride, "Wait, wait! Fuck don't say that it will definitely make me blow. I'll cum in you, but I want you to cum first".

He released her, "OK slow please, cum on me, but ride me slow".

She rode him slowly, but as an orgasm started to build she stopped being so gentle. She bounced on him harder and deeper, moaning, probably making him leak precum uncontrollably in her while she did this to him.

She stiffened up and announced, "Im cumming!" as she bucked her hips on him no longer able to bounce.

She collapsed her little body onto him and I heard him tell her "God, you're just throbbing around me, it feels so good!"

He lifted her back up after a moment and made her work to drain him. He guided her up and down his cock quite hard while her hole was probably pulsating around him. After about a minute of rough pounding he urgently called out, "Are you sure you want this?"

She responded, "Yes, give it to me!"

The words pushed him over the top and he moaned in pleasure as he planted his seed into her unprotected womb.

I stood at the door with my cock in my hand, jerking myself off watching her, she wasn't aware of my presence in her position, but Mike was.

When she lifted off him, cum dripped out of her hole, running down his shaft and balls, onto my bed. Her pussy was opened and I smirked, knowing that Mike finally understood what I meant. She turned onto her back to lay down and saw me standing there, slowly jerking my cock off watching them.

She was surprised but not disgusted. I looked at her, desperately wanting to get in her, but not scare her off. I let her watch me slowly stoke myself and after a few moments I started walking towards her, tucking my cock back into my underwear for a moment.

Mike closed his eyes to recover and I whispered to her, "You looked so sexy doing that. Watching your little pussy stretch to take Mike was the sexiest thing I've ever seen."