How I met hot lil Emory and took her cherry 🍒
So a little about me. I’m 54 years old, great shape, 5ft 9 inches tall. Long story short after the covid pandemic my job wanted me to come back but at half the pay. When I wouldn’t take the pay cut they fired me and after a quick court battle I was suddenly my cities next multi millionaire. Didn’t have to work after that.
I spent my free time on hook up websites and meeting and fucking women of all ages. It was a great life! One day I ended up on a website called Quora, where I got to meet some much younger woman than me, in their 20s and 30s. One day, somehow, in Quora I ended up in a teen room and out of curiosity started scrolling around a bit. Saw a bunch of cute girls asking for people to rate them, so I did. I would tell the girls what I thought of them and even telling them what I would like to do to them. Sometimes people would tell me I was creepy and a pedo for harassing little girls. I would laugh it off and tell them I was actually acting like a hebephile as I was talking to teenage girls. One day I came across this young girl in tight jeans and an olive colored, half tank top which showed off her nice, thin belly and massive teen titties! They were beautiful. I even thought to myself what is this 20 something doing on here. But looking over her profile she said she was 13. I couldn’t believe it. She went on to say she was 5ft and 87 pounds. I was intrigued and after a while of thinking it over I thought what the hell, just introduce myself and compliment her a bit. But with her I sent a private message telling her my name and telling her she was beautiful, which she was. After a couple of hours she messaged me back thanking me and asking what I liked about her. First I told her that I was 54 years old and in all honesty I liked her thin, hourglass figure and her big titties. I told her I really thought she was in her 20s. She lol’ed a bit and thanked me again and said she was really 13. We chatted for a bit and gave me her Instagram account and told me when ever I wanted I could message her there ad she was on there more often. After a couple of days and thinking it over I
Astarted messaging her on her Instagram account. She seemed happy to hear from me.
We chatted for a while and I asked her if she didn’t feel weird talking to a much older man. She told me she did but that older men were always trying to talk to her. Many would run away when they found out how old she was. I told her I still couldn’t believe she was only 13. She took a couple of pic of some paper work with her grades and information from her school. It was a middle school in California, her birthday was in 2010, and she got good grades. I was really talking to a 13 year old, middle school, jailbait girl. I made a joke about that and she said that’s what made her feel comfortable with me, I made her laugh.
After a few days of messaging her she asked if she could call me. On the Instagram app, in the dm’s, there is a way to be able to call whoever you are chatting with. I said sure!
Soon enough, my app rang and I answered. You can do a video call and we did and I was relieved to see she was an actual girl and not some fat old fuck trolling me. She was so cute and wearing a top that was struggling to keep her teenage titties at bay. That first time we talked for a couple of hours. I learned she had never had a boyfriend her age and had managed to keep any man who tried at bay. After a while it got to where we talked daily and she would send me other pics of her that she didn’t post on Instagram.
Our talks got a little more intimate and to my surprise she told me she was a virgin. Couldn’t believe no boy or man had tried anything with. She told me they had but she was scared and didn’t let any of them even feel out her titties.
I got an idea and started asking her size in clothing and she asked why. I found a picture of a little, strapless, black dress and asked her if I could buy that for her. She got excited and said yes. So I ordered it, got her address and sent it to her house. After a couple of days she called me and told she got the dress. She tried just showing it to me.but I told her to try it on. She put down her phone for a bit, then came back on and started to model it for me. My jaw dropped.
She looked so sexy in it. It was a little tight on her, probably since I ordered her a size smaller than she had told me. It struggled to keep her tits covered. It was tight showing off her tite, jailbait ass. It was short showing off her legs.
After that, I got bold and started sending her lingerie and then just sexy bras and panties. She protested at first to modeling them but I eventually wore her down and she would. I couldn’t help but stroke my cock watching her. One day she asked what I was doing, so I angled my phone down to show her. Now, I’m not huge down there but I do have a big, thick, long hard man cock. When I’m fully hard I do measure at a healthy 8 inches. When she saw my cock she gasped and giggled a bit. She told me she had seen one with some 18 year old who tried really hard to get with her. She told me he was tiny compared to me, more like 6 inches.
She asked if I wanted to see her naked. I told her that I would but seeing her in her newly bought lingerie and bras and panties was enough for now.
Finally, she was going to be on summer break soon. I couldn’t believe what I was going to try next. I told her I would be flying into a city close to where she lived and asked if she would like to meet up. She said yes right away but asked how we could do that with out her parents finding out. I told her my plan. I could actually talk to her parents, pretending to be the father of a new friend of hers and asking if she could come over on a Thursday for a sleep over and I would have her home on the following Thursday.
She was scared but I told her not to worry, I could be very convincing. She agreed.
I got my flight to California scheduled and called to let her know. Then she turned off the video part of our conversation and put first her mother then her father on the phone. I talked to them a bit and they both agreed to let her come over. Even talking about spending some time alone as they needed to rekindle their relationship and possibly going out of town themselves. I couldn’t believe how lucky I was!
Day came that I flew out to California. Hell I might of walked right by her parents as they had made a flight out to Las Vegas at around the time I would be landing. To fully impress my lil jailbait girl I had rented a limo. When we got near her town, I called her and told her we were pretty close. I asked if she had packed her lil black dress and the lingerie I had bought her and she had. We finally pulled up to her house and she came outside and got so excited to see the limo. I had already tipped the driver big time to just drive and mind his own business. When he saw her he understood why.
He opened the door for me and I got out. While he grabbed her bags I gazed upon my date for the next 6 days.
She was so tiny but with her big ol titties. She ran into my arms. Her 5ft compared to my 5ft 9 inch frame was quite noticeable. The top of her head didn’t even reach my chin. We got in the limo and driver closed the door behind us. I told her we had about an hour drive. I didn’t want her to be recognized in her little town so I got a hotel room in Santa Barbara on the beach.
We started on our drive. I made sure to close the divider between the driver and the back of the limo. I took out the bottle of champagne and opened it and poured each of us a glass. She was reluctant at first but I convinced her to try it and she finally did.
After a while, I refilled both our glasses because she apparently liked it as she was slowly guzzling it down. After she gulped down her 2nd glass I showed her my next surprise. Being in California I next pulled out a nice big, pre rolled joint. She got all excited but told me she had never tried it but wanted to. Her speech, by this time, had gotten a little slurred. I lit the joint and took a big hit. I slowly blew it out and handed her the joint. By this time I was feeling really good and really took a good look at the lil jailbait girl next to me. So tiny but so busty, she was adorable trying to inhale a hit. I could tell she was struggling so I took the joint and went for my next, bold move. I took a hit, then without inhaling I pulled her to me and put my lips on hers and opened her mouth up and slowly blew the smoke in her mouth. I told her to inhale now and she did. After a couple of seconds she started coughing up the smoke and started giggling a bit. I took another hit and repeated the process, this time she held it in better and could tell between the champagne and the great pot she was starting to feel really good.
We got to our hotel and checked in and I made sure to tip the driver even more. He shook his head and smiled at me. I told him I would need a ride the next day and would call the next day with details.
The bell boy took the cart and led the way to the top floor and to our spacious room. I had to put my arm around my girl and lead her as she was really drunk and stoned. The bell boy apologized saying the room had only one bed, thinking Emory was my daughter or something. I tipped the guy a couple hundred dollars and told him no worries that one bed was enough. He looked puzzled for a bit then realized what was going on and smiled at me, walked out with the do not disturb sign and hung it on the door as he closed it.
Finally alone with Emory! I wasted no time as I walked up to hug her again and pulled back a bit and saw the glazed look on her face as she smiled at me.
She told me that what I did with the joint and her was her first kiss. I looked at her and smiled and told her it wasn’t and I reached down and planted a long little kiss on her then told her that was her first real kiss. She smiled up at me like waiting for my next move. I reached down again and pressed her lips with mine and opened up her mouth and stuck my tongue in her mouth. She got the idea real quick and started twirling her tongue with mine.
I couldn’t believe it, I was making out with a lil 13 year old jailbait girl! I hadn’t done that since I was 15 years old, so long ago.
I hugged her tightly and she returned the hug. After a while of this I thought to myself I had gone this far from convincing her parents to a sleep over at my fictional daughter’s, renting the limo, getting the room at the best hotel in Santa Barbara, with the best view of the beach. How far was I willing to go?
I pulled back a bit to get a good look at this adorable lil jailbait, 13 year old girl. She was kind of out of it being so drunk and stoned for the first time. She giggled and told me to kiss her again. I was planning on that. I had asked her to wear those tight jeans and little half tank top in the first picture o had ever seen her in. I smiled down at her. I reached down with my hands around her bare back and brought them around to her belly and then up, pulling her little tank top off of her. She nervously asked what I was doing and I shushed her. I then reached around her and expertly undid her bra and it slowly dropped to the ground.
She tried to cover her titties but I grabbed her arms and finally looked down at her titties. They were magnificent! Little nipples crowned her breasts. I started to fondle her taunt, tits. They were too young to droop any. They stood up firm and proud on her skinny little body. I reached down and started to grope her teenage titties and started to lick and kiss them. She gasped deeply having that done to her titties for the first time. Everything I was going to do to this lil girl was going to be her first time and that excited me so badly.
She grabbed the back of my head and pulled me tightly against her chest. Got bolder and undid her jeans and with some maneuvering around got them off of her.
There it was, her lil virgin pussy just covered by the panties I had bought her. I slowly pulled them down and gazed upon a picture perfect lil jailbait pussy. Just a few wisps of hair on her pussy, it was the most beautiful thing I had ever seen. I stuck out my tongue and slowly slid it across her opening and she almost melted on me. I licked up and found her lil clit and dragged my tongue against that. She let out a loud groan and I started eating out that lil pussy for all that it was worth. She steadyed herself holding on to my shoulders itightly and I continued eating out that lil pussy. She tasted so fresh. Her pussy was getting so wet.
She groaned and gasped loudly and reached up and pulled my face deep into her pussy as her very first orgasm rocked her little girl body. I lapped up as much as her pussy juice as I could and there was so much that it dripped down all over my face. After a while she started to calm down and I had to reach up and grab her before she fell over. I stood up while getting her gently on her knees and I started to pull off my pants. She wouldn’t look at my bulge just yet, but little by little she looked down at it. I guided her hands and had her pull of my underwear and I kicked them off. My cock bounced off her face and she shyly looked at my cock. She said it was much bigger in real life. I smiled at her and told her to hold it. She tried to wrap her lil hand around my big, hard cock but ended up using both her hands as she started to stroke my cock. I groaned loudly and looked down on her and told her to open her mouth. She did and I had her guide my cock head into her mouth . She barely could but finally get the head into her mouth. It was an incredible feeling and I knew I wouldn’t last long anyways. She knew instinctively to lick my head, twirling her tongue all around it. I was right and could feel my orgasm building up. Slowly my supermarket started building up and
grabbed the back of her head and pushed as deep as I could into her mouth. She protested and gagged until I started squirting load after load into her mouth. I held her head in place as she gurgled my sperm out and it leaked out the sides of her mouth. She had no idea what she was doing but still was the best blow job I had ever had. Let go of her head and she spit out my cock and what sperm she still had out of her mouth she scolded me for doing what I just had done. I looked at her and couldn’t help but think of how cute she looked as she drunkenly scolded me. She was slurring her words so much by now. I laughed as I bent down and picked her up and led her to the bathroom and had her brush her teeth and had her gargle some mouth wash. When she was done spitting it out I picked her up and carried her to the bed and laid her on her back.
I looked down at her and thought to myself that I had gone this far, might as well go all the way. I got on the bed and spread her lil legs apart and lied on top of her between her spread lil legs. Being how short she was, as I kissed her I couldn’t feel her pussy with my cock just yet. As I kissed her she groaned into my mouth. After a while I slid up her lil body and started rubbing my cock on her little slit and opening of her little, virgin pussy. She started breathing fast and hard. She asked if I was going to make love to her and I laughed and told her I was going to fuck her. She asked me to please be gentle as it was her first time and I was like yeah, sure, whatever. My cock got hard as a rock and I pushed up with one hand and used the other to guide the tip of my cock to her teeny tiny little virgin opening. She gasped as she felt my tip slowly start to enter her. I pushed a little and got just the tip in. I stayed like that for a few seconds then pushed my head in and felt her virginity open up to me. She squealed loudly and I groaned loudly as I felt her tightness around the head of my cock. She begged me to pull out ,that my cock was too big and I was hurting her. I looked down at her as I squeezed another inch into her teeny, tiny, lil 13 year old jailbait, virgin pussy. It was heaven to me as she wrapped her arms around me and screamed no, for me to pull it out, that I was hurting her so badly. I had only 2 inches in her at that time. I told her I knew I was hurting her but that she would get used to it. Didn’t know if that was true but I didn’t care at that point. I lay like that for a bit as she got used to those 2 inches and she gripped my shoulders tightly and dug her finger nails into my shoulders. Couldn’t hold back any longer and quickly shoved 2 more inches into her tight pussy. She tilted her head back and screamed as she felt 4 inches of my cock sliding inside of her.
I slowly started to pick up the pace and started fucking her. After a while I managed to fill up her pussy with about 6 inches of my cock. She was so tight, I could feel every nook and cranny. I could feel my tip slowly spreading her opening to her womb. I fucked her harder and harder. I could feel my sperm start to build up and I told her I was going to cum. She freaked out, still screaming and started to push up on my shoulders and yelled at me to pull out, that I couldn’t cum inside her since I wasn’t wearing a condom, that she couldn’t get pregnant, please pull out. I slowed down a hit and looked down at her and told her ok, that I wouldn’t cum in her.
With my left hand I slid it down her back and cupped both her tight little ass cheeks and slid my middle finger between her Crack along her ass hole. Top of her head barely reached my chin and I grabbed the top of her head with my right hand and held in place like that as I quickly started pushing in and pulling out over and over again. I was fucking her fast and hard now, while she squealed and screamed. She suddenly wrapped her muscular little legs around my waist and picked her ass off the bed pulling me into her pussy. I could feel my thick, creamy load flowing through the length of my cock and yelled out I was going to cum inside her. She yelled out no, please no but kept her legs wrapped around my waist. I couldn’t pull it out if I wanted to. As I was about to cum I pushed through her opening of her womb and the last 2 inches of my cock slid in her. I held her in place with my hands on her ass cheeks and the top of her head and started pumping her even harder deep into her womb as the first big, thick wad of my baby makers splashed into her. She felt it splash deep in her womb and started to scream but not in pain but rather with pleasure as her first orgasm with a cock inside her tool over her little, jailbait body.
I pumped into her over and over again as I fucked deep into her womb as splash after splash of my baby making sperm splashed deep inside of her. She kept pulling me deeper into her with her legs wrapped around me. The feeling for me was incredible. I had died and gone to heaven. Each squirt seemed bigger and bigger. Finally all good things must cum to an end as my orgasm died down and I had no more sperm to give her. I collapsed on top of her tiny little body my cock slowly shrinking out of her no longer virgin pussy. I had done it! I fucked a tiny little 13 year old virgin pussy and filled her with my baby makers. I laughed as I felt so proud of myself. I slowly got off of her and walked over to the love seat in our room and sat in it. She started crying about how she was going to get pregnant and how could I cum in her. I told her her pussy was just to good to pull out. I thought back to how good it felt as I came inside her tight, tiny, little teenage, virgin, 13 year old jailbait pussy and just laughed out loud. I patted my seat next to me motioning for her to come over. She finally did and curled up next to me and let me hold her as she cried.
Stay tuned for the next few days of our weekend together. Sorry so long but now that the scene is set the next stories should go quickly.