Author’s Note: By popular demand, here’s chapter 2 in my hitchhiker story. Make sure to follow along because I now have seven chapters and this thing takes some amazing turns.
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The rest of that day was the usual football Saturday and we went to a local watering hole to eat wings and watch our team. My mind kept going back to Mary Ann and my cock would start to get hard every time it did. I had fantasized for years about picking up a hitchhiker and jacking off in front of her and I had a couple near misses in the past but nothing like this. To have a girl almost 40 years younger than me lust after my cock is blowing my mind. And that young pussy is so tight and soft. Things change as women get older and there is nothing like a young girl.
Mary Ann and I started to share secret texts and she added me on Skype so we could have private conversations. She started sending me naked pics but that quickly evolved into cam sessions where we both got naked and masturbated for each other. This also allowed us to plan our next date. As I told her, my wife was going to Florida for a week in October and we started to plan our next date. I confirmed that she’d have her room to herself on a Tuesday while my wife was away so I put in a request at work to take the day off. Everything was set but we still had two weeks to wait. After we got each other off during our next Skype session I suggested that we both abstain from sex until we met in order to make the most out of our date and she agreed. Personally this was going to be tough but I was intrigued to see how big of a cum shot I’d have with two weeks of abstinence and how many times I’d be able to cum. I was sure it was going to be sensational and I’d be able to fuck Mary Ann until she could not cum anymore.
Finally the day arrived. I woke up at 7AM, showered and shaved and put on a golf shirt and shorts with no underwear. I wanted to look nice for Mary Ann but I was sure the clothes would be an afterthought. I went downstairs, got a cup of coffee and sent her a message on Skype to make sure she was ready. She replied that her room mates would be gone by 9AM and she was getting ready to shower and make herself perfect for me. I had a thought that since we would be occupied with having sex all day she might appreciate it if I fed her at some point. I didn’t want to take time taking her out so I packed a bag full of eggs, cheese, potatoes and bacon so I could make her a nice breakfast in between our fuck sessions. I knew exactly what I was going to do to her first and she would definitely need time to recover. Plus I was sure college students don’t keep a lot of food on hand and I loved the thought of treating her to an amazing breakfast. I packed my supplies, left the house at 845AM and on the drive to her apartment I pulled my shorts down to my ankles and stroked my cock in anticipation.
I arrived at 915 AM, pulled up my shorts but my cock stayed rock hard as I knocked on her door. I gasped when she opened the door and was completely naked. Her eyes were wide as she noticed the huge bulge in my pants and said, “My oh my. It looks like someone is ready to show me a good time. Get in here you stud and fuck me.”
I entered the apartment, set my supplies on a table and she asked, “Did you bring me something?”
I replied, “I sure did but it’s a surprise that I know you’re going to really enjoy. First I need to ravage your young body because my balls are aching for you since I haven’t cum in two weeks.”
“Me either baby. A couple guys tried to hit on me and it was nice telling them to get lost knowing I had this to look forward to.”
She locked the door and added the chain lock as well just in case anyone came home unexpectedly. Then she took off my shirt and shorts and pushed me down on the couch, started stroking my cock and kissing me. “God I so need your cock. I want to jump on it right now but we should take our time since we have all day.”
“Thats right babe. Today is the day when all your fantasies come true and you get to do whatever you want with me. I want you to sit back and play with yourself first.”
“Oh fuck yes. I’ve always wanted to do that but was afraid to ask.”
She leaned back on the coach, pulled both legs up onto the cushion and started playing with her pussy as I stroked my raging cock. “Oh daddy I feel so naughty when you watch me play with myself. Stroke that fucking huge cock for me. This feels so fucking good I can’t stand it.”
“You are perfect Mary Ann. Feel that clit and get that perfect pussy nice and wet for me. I love stroking my big cock while you watch. I didn’t get to see your ass when I picked you up and I have a huge ass fetish. Get on your hands and knees so I can see your ass baby.”
She did as I asked and continued to play with herself as I got on my knees so she could still see me jacking off. She had the most perfect round ass and it had some size to it for such a tiny girl. I couldn’t resist anymore and started licking her ass. I slid my tongue all over both ass cheeks and slowly made my way to her asshole. I teased around the outside at first as she moaned with pleasure and finally stuck my tongue as far into her ass as I could.
She cried out, “Oh fucking hell Tony. No one has ever done that to me before. It feels so fucking good I could cum right now.”
I pulled my tongue out and said, “No, no little girl. I need to bring you along slowly this morning so you have an orgasm that will blow your mind. Remember we have all day and there’s something I need to do right now.”
Her ass was wet from my tongue and I put my cock between her cheeks and started to grind her sweet ass. “Fuck Mary Ann, your ass feels so amazing on my cock. You are so fucking hot I feel like I could cum right now!”
She teased me by saying, “No, No daddy. Remember we have all day and you need to build up to that mind blowing orgasm.”
I sat back on the couch, pulled her to me and we started to make out. She smelled so fresh and clean it was driving me crazy. I picked her up and sat her on my lap as we continued our passionate kiss. We explored up and down our bodies and rubbed each other as any tension melted away with our touch. My raging cock poked between her legs and she started to grind her pussy on it. She was already soaking wet and I thought about grabbing a towel for the couch but there was no way I was going to interrupt this.
“Oh Tony your cock feels so good and the way you caress and massage my body is so fucking amazing. Never in my wildest dreams did I think I’d meet someone as perfect as you.”
“How do you think I feel Mary Ann? You’re almost 40 years younger than me. I never thought I’d have a chance with a girl like you.”
“Really Tony? You don’t realize how fucking handsome you are and that bulge in your pants is always noticeable even when you’re not hard. I know women and you could have anyone you want anytime.”
“No way Mary Ann. Women don’t think of me like that. I’m sure I’m just another old bald guy to them.”
“I disagree and someday you and I will put that to the test and maybe a little wager as well.”
“A wager huh? We’ll try that experiment someday but right now I need my cock in your pussy. Where’s your bedroom?”
She pointed to the back of the apartment and I picked her up and carried her to her room. “This is so fucking sexy I can’t stand it. I’m sure I am going to cum the second you stick your cock in me.”
“Don’t worry doll baby. I know how to bring you along slowly.”
I laid her down on her bed and kissed the length of her body, spending a long time on her little tits, before I positioned my massive cock outside of her pussy. I pushed only the head in and she was just as tight as the first day we met but I was going to tease her with the head of my cock this time.
I pulled out, rubbed the head of my cock on her clit and she cried, “Oh fuck thats going to make me cum right now Tony!” I didn’t want that so I backed off and slid the head of my dick in her pussy, slowly pulled out, back in and out again. “You’re driving me crazy Tony, please stick it in me.” Her legs were shaking and her ass was bouncing off the bed as she tried to get my cock but I kept just the head in her.
Next I pulled all the way out and started to jack off. “I don’t think you’ve earned the right to have my cock in your pussy Mary Ann. I think I’ll just sit here and jack off until I make myself cum.”
She started to beg, “Oh please Tony, please. I need your cock and I’ll do anything to get it.”
“Oh really, anything?”
“Yes, anything you want. I have to have your cock or I’m going to go crazy.”
“OK then lick my asshole” I commanded. She immediately got behind me and stuck her tongue all the way up my ass. “Oh yes now reach around and jack me off and squeeze my balls with your other hand.” She did as she was told and it was heaven on earth. Having her tongue go in and out of my ass while she stroked my cock and squeezed my balls was unbelievable. I enjoyed this for several minutes then said, “OK Mary Ann, you’ve earned the right to have my cock. Lay down on the bed.”
Without saying a word she lay down and spread her legs. A puddle of pussy juice immediately started to form on the bed. I then began to slowly push my raging eight inch cock in her tight young pussy. This time there was little resistance and I slide all the way in and held my cock there. I pushed even harder and she cried out, “Oh my God that feels so fucking good. My little pussy never felt so full. I’m gonna fucking cum all over your cock.”
Before she could I slowly eased my cock out and held it just outside her pussy. “Oh no Tony I can’t take more teasing. Please fuck my pussy. Push it all the way in again.” Tears started running down her face as the need overcame her. I took mercy on her and slowly pushed my cock all the way back in. Before I could pull out again she sunk her fingernails into my ass and wrapped her legs around me and started grinding her clit on the base of my rock hard cock. The feeling was incredible but I slapped her hands away and pulled out again.
“You will thank me for this when I finally make you cum Mary Ann.”
Tears were pouring down her face as she cried, “Oh please daddy, please put it back in. I have to have your cock.” I paused a bit longer then slowly pushed in and back out. I continued with long slow strokes stopping occasionally to grind the base of my cock on her clit. “Oh fuck I think I’m going to pass out from pleasure.” I continued with long slow strokes and finally buried my cock once more up to the base. Once again she dug her nails in my ass and ground her clit so hard against my cock it hurt. She cried, “Oh fuck I’m finally going to cum. Oh Jesus Christ I need your cock to make me cum. Fuck, fuck, fuck daddy I’m cumming! Oh God now! MMMMMMMM!” As she came, a flood of pussy juice flowed from her cunt making a huge puddle on the bed. “Fuck I can’t stop cumming! Oh I’m going to die from the pleasure. I love you so fucking much I never want to let go of your cock. MMMMMMMM Fuuuuuuuck!”
When she was finally finished I said to her, “Do you remember what I told you the day we met?”
“What? Right now I can’t even remember my name.”
“I told you I would make you cum multiple times in a row and that’s just what I’m going to do now.”
“You can’t possibly make me cum again so soon after that mind blowing orgasm.”
“Just watch me,” I said. I moved my body higher up so that my cock bent at an angle and hit her g-spot.
“No way I can cum again,” she mumbled. With my cock fully inserted I started to pound her little pussy as hard and fast as possible. Her eyes opened and she cried, “Oh God Tony. What are you doing to me with that wonderful cock? It feels so fucking good I’m going to fucking cum again. I can’t believe it. MMMMMMMMM!” She sprayed another torrent of cum all over her bed.
“Oh fuck that was incredible. I don’t think I’ll ever cum again.” I paused for half a minute and pushed back in. “No way Tony, there’s no way I can cum anymore.” I pounded her pussy again and she immediately had another orgasm. “Oh Jesus, I’m cumming again! MMMMMM!” I waited another 30 seconds then pounded her again. “Oh God daddy, please stop. I’m going to pass out! MMMMMMMM Cumming! Cum, cum, cum, fuck!” Once again I waited and pounded her again. “No please don’t! I can’t stand it. Oh fuuuuuuuck! MMMMM”
I whispered in her ear, “You’re not done yet sweet thing” and pounded her again. She came again with more tears running from her eyes and said, “This isn’t possible. MMMMMMM!”
“Yes it is baby” and I pounded her again to another orgasm. She could only whimper at this point. This orgasm was smaller so I knew she was almost done but pounded her once more to another orgasm.
I pulled out of her pussy and stroked my raging cock. “You came eight times Mary Ann. Now do you doubt what I can do?”
“My God Tony. Oh my fucking God no.”
I knew she was totally spent so it was my turn to use her young body any way I wanted so I rolled her over and slid my cock between her ass cheeks as I massaged her back. She said, “I am in total heaven right now and I never want this to end.”
“Your ass feels so good on my cock little girl. MMMMM.”
“I’m so glad you like my ass daddy. All I want to do is please you.”
I continued to grind my cock on her ass and then I positioned my cock on her tight little asshole. “Get ready my little doll. This is going to hurt a lot,” and I started to push my cock in her ass.
“Oh no Tony. I can’t do this. My ass is too little. That really hurts me. Please don’t.”
“I thought you wanted to please me little girl and this is what I want.” I pulled out and then eased my cock a little further into her tight ass.
She cried out, “It feels like you’re tearing me apart. Oh it hurts so bad. Please stop, Please!” Tears continued to stream down her face as I pulled out again and this time I was able to push all eight inches of my hard fat cock all the way into her ass.
“I can’t take this. Please take it out. You’re really hurting me.” I pulled out and slowly inserted my cock once again then started to pound her ass like I pounded her pussy.
“Oh God that hurts so bad. I’m gonna pass out.”
I knew she was on the brink of accepting my cock as I continued to pound her little asshole.
“Oh fuck I can’t believe it Tony but I’m going to cum again. How is this possible? MMMMMMM fuck my ass daddy like I’m a little whore!”
The puddle of pussy juice expanded as I felt my own orgasm begin to build. “Fuck Mary Ann I am going to fill your asshole with a huge load of cum right now.” I took long slow strokes in and out of her asshole and then with just the head of my cock in her to maximize the pleasure of her tight muscle. “Oh fuck here it comes Mary Ann!” I then buried my cock as far as I could in her ass as I started to cum. “Oh fuck, you feel so good. MMMMMM take my cum in your ass doll. Oh yes, yes yeeeessss!” My cock spasmed as I unloaded two weeks worth of sperm into her asshole.
I collapsed on top of her with my cock still in her ass. She tried to roll over but I held her down until my cock finally softened.
“I have no words to describe what you just did to me.”
“It’s called pleasure my love.”
She asked, “How do you know how to do all that?”
“I’ve been around the block a few times Mary Ann and I have a few more tricks up my sleeve.” I looked at the clock on her nightstand and it was still only 1030AM. “What time are your room mates due back?”
She said, “Not until four.”
“Five and a half more hours of pleasure to go then.”
To that she said, “God help me.”