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 blows 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 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. Since my wife was going to Florida for a week in October I confirmed that she’d have her room to herself on a Tuesday and 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 phone 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 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 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. Right now though my pussy is aching with desire for your big cock.”
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 too shy to ask.”
She leaned back on the couch, 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 on 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 who made me feel like this.”
“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 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 little girl. 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 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 daddy, 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 was forming on the bed as I slowly pushed my raging eight inch cock in her tight young pussy. This time there was little resistance and I slid 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, 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.
“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 this so fucking much I never want to let go of your cock. MMMMMMMM Fuuuuuuuck!”
It took a few minutes for her to recover and she said, “My God Tony, I can’t believe what just happened to me. I’ve never felt anything like that in my entire life.”
I said, “I’m glad you enjoyed it. 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 as I moved my body higher up so that my cock bent at an angle and rubbed against her g-spot.
“No way will you be able to make me cum again,” she mumbled. With my cock fully inserted I started to pound her little pussy hard and fast. Her eyes opened and she cried, “Oh God Tony. What are you doing to me with that wonderful cock? It feels so fucking good, my little pussy is going to cum again. I can’t believe it. MMMMMMMMM,” and she sprayed another torrent of cum all over her bed. “Fuck that was incredible.”
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 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. Grinding my cock on your ass is one of my favorite things to do. 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 it 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. Your dick is way too big for my little ass. 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 streamed 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 tight 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.
She cried out, “Fuck it hurts so bad, I can’t take this. Please stop.”
I knew she was on the brink of accepting my cock as I continued to pound her little asshole.
“Fuck, OK, I’m getting used to it now and it doesn’t hurt as bad but I hope you cum soon.”
I said, “Patience little girl.”
As I continued to pound her ass and pain turned to pleasure she said, “Oh my, that’s starting to feel good. Oh yes daddy, you always know what’s best for me. Pound my little ass!”
I changed between fast and slow strokes as her pleasure continued to build to another orgasm.
She cried out, “I can’t believe this, I’m going to cum again. I didn’t think it was possible to cum this way, it feels so fucking good! MMMMMMM fuck my ass daddy like I’m a little whore! Fuck I’m cumming right now, MMMMMM!”
As the bed became wetter with her orgasm 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. She said, “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.”
I chucked then asked, “Are you ready for your surprise now little girl?”
“I can hardly wait to see what you brought me” she replied.
“Follow me then.” I went out to the front room, grabbed my bag and took it into her kitchen. Before unloading I said, “I knew exactly what I was going to do to you this morning and after cumming so many times you’d need time to recover. I thought I might take you out to breakfast but I didn’t want to waste that much time so I brought breakfast to you. How does cheesy omelets, bacon and home fries sound to you?”
“Oh my God Tony, I’m absolutely starving. I ran out of money and haven’t had anything to eat since yesterday morning. I don’t get paid from my crappy job until Friday so I have a rough couple days ahead of me. I can’t believe you thought to do this for me.”
I said, “I figured you might be struggling a bit so I have something else I want to give you.” I retrieved my wallet from my shorts and pulled out the ten 100 dollar bills I withdrew from the credit union yesterday. “I want you to take this and there will be no arguing. Also, anytime you find yourself in a bind I expect you to call me and let me know. I have the means to take care of you and there is absolutely no reason for you to go hungry.”
Mary Ann looked at me with tears in her eyes. “I don’t know what to say Tony. I did not expect you to do this for me and I feel guilty taking your money. I hope you don’t feel like you need to pay me for sex.”
“Did you not hear what I said? If I couldn’t do this I wouldn’t but I couldn’t live with myself if all I did was take advantage of your body while you struggled with life. So there will be no debate here little girl. Put this money in a safe place while I make you breakfast.”
Now the waterworks really started and she encircled me in a loving embrace. “I don’t deserve you,” she cried and continued to sob into my chest.
“Now, now Mary Ann you just stop it. I am happy to do whatever I can for you so let’s not ruin our day with guilt and remorse. Put the money away then come into the kitchen and watch me cook.”
She did as she was told and returned as I prepared breakfast. “You are an amazing man. What is it that you do for a living?”
“I’m the Chief IT Analyst at Graham Insurance in the city. Basically I solve problems and they pay me a lot of money to do it. This is my 28th year and that place has been very good to me.”
“Oh my God Tony! I am studying Comp Sci here at The Boro! How ironic is that?”
“I’d say that’s pretty ironic so here’s what you are going to do. Get your laptop and go to the company site and apply for an internship. List me as a reference and I’ll make sure they hire you. We pay our interns so your money problems will go away. After graduation I’m sure you will be hired into our Apprentice program and you’ll be set for life. We have way more work than people and the company has asked for everyone’s help with recruiting top talent.”
“I can’t believe what is happening to me right now” she said. “I hope you are being honest with me.”
“What have I done so far that would make you doubt me? Now go get the fucking laptop and apply online before I get pissed.” She got a frightened look on her face and I smiled and said, “Jesus Mary Ann, can’t you tell when a guy is kidding?”
She went to her room, got her laptop and submitted her application while I made her breakfast. “Tomorrow when I’m back in the office I’ll go right down to HR and have them pull your application. You should have an interview this week and I’ll make sure to coach you up so you’ll ace it.
“I think I’m falling in love with you Tony” she said.
“That’s nice of you to say sweet thing. Let’s enjoy the moment and let things play out, I promise I will never disappoint you.”
Breakfast was ready and I piled her plate high. She ate ravenously and finished everything before I was half way through. “That was fucking amazing” she said as she piled the remaining food on her plate and finished that as well.
I said, “For such a tiny thing you can sure pack it away little girl.”
“I couldn’t help it. It tasted so good and I was so hungry, thank you again.” When I finished she told me to relax while she cleaned up. “I can’t stand a mess in my kitchen and there’s no way I’m letting you wash dishes stud.”
“A woman after my own heart” I said.
I relaxed in my chair and admired the view as she washed the dishes. Her belly was perfectly flat but she wasn’t too thin so her body was perfectly soft. I admired her legs as they met the swell of her ass and her firm young tits. Her beautiful face and bright blue eyes were stunning, especially for a brunette. My cock was getting hard so I started to jack off while I continued to gaze at her perfect young body.
She didn’t notice until the clean up was finished then she turned around and said, “Holy shit Tony, you’re hard again already! I don’t think I can fuck you again just yet as both of my holes are sore.”
“Well, you have another one that I haven’t used yet today so why don’t you start sucking my dick?”
Without saying a word she grabbed a cushion from the living room, placed it in front of me, knelt down and sucked the head of my cock into her mouth. As she sucked my cock I marveled at my luck in finding this beautiful sweet girl. I was happy to help her in any way I could and when she gets hired by my company I will have ready access to her body to take care of my constantly hard cock.
“Fuck yeah Mary Ann, that feels so nice. I love the way you suck my cock. Remember to suck my balls and squeeze them too. I love that.”
“I love the taste of your cock and will suck it anytime you want me to but I wish I knew how to get the whole thing in my mouth. I can’t wait to swallow what I know is going to be another big load of cum,” she said while she jacked me off.
“Fuck that feels so fucking good and if you want to learn how to take my whole cock in your mouth I can teach you.”
She said, “Please tell me how daddy, I want to learn how to please you.”
“You always please me but if you want to suck my entire cock just relax your throat. You might only be able to keep it in for a little while at first but eventually you’ll learn how to control it.”
“I’ll try daddy,” and the first time she took my whole cock she immediately started gagging.
“Good job little girl but you need to relax your throat more. Don’t worry, it will stay hard and I’ll be patient with you.”
She said, “OK, I’m ready to try it again.” This time she slowly took the whole length of my cock into her mouth, down her throat and held it there before sliding her lips back up the length.
As she jacked me off she said, “I did it daddy, I hope you’re proud of me.”
“Yes you did little girl and it felt wonderful.”
As she gained more confidence she swallowed my raging shaft and altered the pace from long and slow to hard and fast. “That’s my good little girl, you’re doing great and it feels really good on my big cock.”
I sat back and enjoyed the view as she swallowed my cock and it felt totally amazing but I needed her sweet ass again. I grabbed the bottle of olive oil I brought to cook breakfast and asked her to get up and turn around. “You are an amazing little cock sucker but I need to feel your sweet ass on my cock again doll baby.”
She said, “You know you can do whatever you want to me Tony but I don’t think my ass can take your cock again right now. I’m not sure when I’ll be walking normally again after the pounding you gave me with your big dick.”
“I realize that and don’t intend to do that again just yet. I think you’re going to like this.”
I got up and put a cup of oil in the microwave and warmed it for a minute then sat back down and drizzled a generous amount on her back and ass. I positioned my cock between her ass cheeks and said, “OK Mary Ann, hump my raging cock with your sweet young ass.”
She proceeded to grind her ass slowly up and down the length of my shaft and it felt totally incredible. I watched my cock slide up and down her ass then added more oil to her back and started to give her a back rub.
“Oh Tony that feels amazing. Your hands are so strong I can feel all the stress leaving my body.” I massaged her neck and her shoulders with great pressure which caused her to moan and hump my cock with greater urgency. I made my way down her back then poured oil over her perky tits and attended to her little nipples which were hard as rocks. I also made my way down to her little clit as well. “Fuck that feels so fucking good on my tits and my little pussy. I didn’t think there was any way I’d cum again but you are making me so fucking hot!”
As I continued to massage her entire body she started to grind my cock from her ass to her clit. When I made contact with her clit she started grinding my cock hard and she cried out, “Fuck you fucking stud you’re going to make me cum again right now. Oh my fucking God I’m fucking cumming! MMMMMMMMM Yeeeeesssss!”
With that she unleashed a huge torrent of pussy juice all over my cock, stomach and chest. I then reached around and tweaked her clit really fast with my hand which caused her to spray more pussy juice all over me. “My God I can’t believe I’m doing this. I’ve never squirted like this before in my life.” I continued tweaking her clit and she continued to cum and spray me with her juices until she finally collapsed on the kitchen floor.
“I’m sorry Tony but you are driving me absolutely crazy. Let me take care of that cock now.” She recovered and started to greedily suck my cock down her throat. Then she reached over to the table and grabbed the spatula I used for breakfast and shoved the handle deep into my ass while squeezing my balls.
“Oh fuck Mary Ann that is fucking amazing. Oh it feels so good. Fuck my ass harder and squeeze my balls. I’m going to shoot a huge load of my cum down your throat.” She continued to suck and fuck me as my orgasm started to build. Then she slowed her pace, keeping me on the edge for what felt like an eternity.
“Goddammit I’m going to fucking cum right now!” I grabbed her by the sides of her head, stood up and fucked her face hard and fast as I began to shoot my load down her throat. Wave after wave of cum spewed from my cock into her mouth and what she couldn’t swallow fast enough leaked from the sides of her mouth, down her neck and onto her tits. I rubbed it in as she continued to suck my cock until finally my orgasm was complete. She swallowed all the cum I gave her then straddled me, leaned my head back and kissed me passionately with her tongue nearly down my throat.
“That was some fucking orgasm Tony. I didn’t think you were ever going to stop cumming. You are incredible and I feel like the luckiest girl in the world. I can’t wait to go again.”
It was just past noon and I said, “I think you should show me your bathroom. I have an idea that will soothe your body and get you ready for more fucking.”
She said, “I can’t wait to find out what’s next,” as she led me to the bathroom.
As we walked through I took a good look at Mary Ann’s living space for the first time. It was pretty old but surprisingly well maintained for a college apartment. There were three bedrooms so she must have two room mates and I made a mental note of that for later. There was the small kitchen and living room with decent furniture so the girls must have brought their own stuff. It was located next to Wallboro Lake with a nice sized window overlooking the lake. There was only one bathroom and that had to be a lot of fun with three girls. The shower was rigged up inside a large old bathtub so there was plenty of room for two.
I said, “I really like your place Mary Ann. You take good care of it.”
“Thanks Tony. Between the three of us we are all pretty OCD when it comes to being clean.”
“That’s great and this old tub is perfect for two. I see you have bubble bath. Draw us a nice hot bath and don’t skimp on the bubbles.”
I sat back on a clothes hamper and admired the view of her ass as she bent over to draw our bath. Once the temperature was to her liking she walked over and kissed me. She looked into my eyes and said, “I really hope life is good to you. You’re so kind I could see how some people might try to take advantage.”
“That’s nice of you to say but I’m fine now that I have you,” and we kissed again.
The bath was ready so we got in with our heads initially at opposite ends and as we sunk down our bodies were positioned perfectly. Mary Ann cooed, “Oh this feels so nice on my aching pussy and ass.” I grabbed her foot and slowly started to massage it. “Oh my goodness, that’s heavenly Tony.” I massaged the other foot and down the length of her tight legs. The hot water did feel really nice as did her ass as it was positioned on top of my cock. I continued to caress her feet and legs and noticed her breathing had slowed. She had actually fallen asleep. I leaned back and soon was napping as well.