I wish this had happened to me. This is my first try. Let me know your thoughts. [email protected]

Hitchhiker
Story of older woman (55 y.o.) getting a ride from a 17 y.o. boy

My name is Tom. I am 17 and just got my license. My dad took his time taking me to the license branch so that is why I was a little late getting to drive legally. Most of my friends have been driving for almost a year already. Anyway this is the story about my first time.
Let me start by describing myself. I am 6’ tall, dark brown hair, hazel eyes and about 150lbs. Tall and skinny. I am not very good looking at all. Whenever I am out with my friends I am the one who the girls never look at. I have a good personality and I am always smiling, but he opposite sex is just not attracted to me. I have friends that are girls, but no girl friends. Anyway you can imagine how much I masturbate? A lot!!

So my story starts one Saturday about two weeks after I got my license and my Dad felt comfortable enough for me to drive by myself. I got up early and washed my car. It is a 1981 Cutlass Supreme. I love that car. I have worked very hard for it and I take very good care of it. Anyway after I finished washing my car I got a call from my friend Mike. Mike has been my best friend since the second grade. We do everything together. Swimming in his pool, hanging out in his basement and sleeping out in his tent on weekends. He is a great guy. I get a little jealous sometimes as he is very popular with the ladies. I remember one time I walked in on him and he had a girl lying with him on his bed. Her shirt and bra were off and he was playing with her creamy white titties. They were beautiful and I could not take my eyes off of them. They were the first set of real titties I had ever seen. Playboy was nice, but nothing like seeing a real pair of boobs. Anyway I stared a little too long and the girl started to scream. Mike told me to get the hell out of there! So back to my story. Mike called and said his car broke down and he needed me to pick him up. I got in my car and headed to him.

On the phone he told me he was on the west side of town. Not sure what he was doing there. We were from the east side and pretty much stuck to our own side. I hit the interstate and before long I was cruising the west sides back roads. I saw a few junk yards, some “mom & pop” convenient stores and a lot of pawn shops. I was supposed o meet Mike on the corner of 18th and Wabash. I sort of got lost, but eventually pulled up to the curve. Just as I was pulling in my phone rang. It was Mike. “Hey Dude its Mike. I hope I caught you before you got too far?” I responded that I had just pulled up to the corner where I was supposed to meet him. “Oh sorry Dude” said Mike. “My sister’s boyfriend was in the area and has already picked me up”! “Damn” I said. Mike apologized and said he would make it up to me later.
I checked my mirror, waited for a car to go by and then started to put my car into gear. “Hey Hon” I heard a raspy female voice say. Where did that come from I thought to myself? I looked over at my passenger side window and saw an older woman looking at me. She had short black hair, black eyes, a small nose, red lipstick, a shiny pink shirt and a black jacket on. From what I could tell is that she was tall and skinny like me. “Hello Mam” is all I could say. “Mam?” she responded “How old do you think I am Hon?” Before I could answer she extended her hand and introduced herself. “My name is Ronnie and you are?” I told her my name and just sat there. “Listen Baby doll my legs are tired and I need to get to my room, could you give me a lift?” I thought for a second and then asked “How far away is your room?” She told me it was only a few blocks away in a local motel. I said sure. She opened the door and as she got in I could see the lower portion of her body that was hidden by my car door previously. Just I suspected she was thin. She had a very small waist and long skinny legs. I tried not to stare and be rude. She got in and sat down. She was wearing a black skirt that matched her jacket and panty-hose that had lines in them. She also had very long black high heels.

As soon as she was settled she reached into her purse and pulled out a cigarette and lighter. I really did not want her smoking in the car, but I did not say anything. “Pull out and go straight Hon” she said as she lit her cigarette. I did as she said. As I pulled from the curb and started to pick up speed she turned to me and said “you don’t mind that I smoke do you?” I told her I did not mind at all. As we were driving she was giving me directions and making small talk. She asked how old I was and if I had a girlfriend. I told her I was seventeen and was not seeing anyone currently. She then commented “oh so you normally have a girlfriend just not right now right”? I admitted to her that I did not have a girlfriend now nor have I ever had one. She just smiled to herself and lit another cigarette. After a few minutes she told me to make a right and then to pull into a parking lot of an old dilapidated building. I did as I was told.

I pulled into a parking space and put the car in park. I did not turn off the engine because my plan was to complete my good deed and get the hell out of there!! “Thank you so much for the lift Hon.” Ronnie said. She grabbed her purse, opened the door and lifted herself out of the seat. I stared forward because I did not want to be tempted by looking at her back-side. Suddenly I heard a yelp and looked over at where Ronnie had just been seated. I was startled as I realized she had fallen and was lying on the pavement outside of my car. I jumped out of the car and went to the passenger side to help her up. “Oh shit!” is all she said. I kneeled down beside her and tried to help her up. She turned her head toward me and screamed to leave her alone. I stood back up and just stared. Finally she looked at me again and apologized. “Hon I am sorry, can you help an old lady up?” As I was helping her up I told her that she was not an old lady. I told her that I thought that she looked great and I thought she was very pretty. I think my comment caught her off guard because as I lifted her to her feet she turned head toward me and smiled. “Thank you Hon that was very nice.” “55 by the way” she said. “What” I asked. She said she was 55 y.o. I told her that I thought she was gorgeous no matter her age. She really was too. Now that she was standing straight up and I had an opportunity to really get a clear view of her. I thought she was extremely sexy. Long legs, small butt, pretty face. The one thing I did notice was that her boobs were barely noticeable. After seeing Mike playing with that girl’s tits I really made sure to notice these types of things.

I got Ronnie up on her feet and balanced her on my shoulders. She wrapped an arm around my neck and made sure she had her purse. She kicked her heels off and asked if I could stoop down and pick them up. I obliged. Once I had her heels and she was balanced she asked me if I could help her to her room. I told her I could, but I had to turn off the engine. She said not to bother because her room was close and we would only be a couple of minutes. I hesitated, but decided it would be OK. We started to her room very slowly. As we approached her room she reached into her purse and took out her key. She handed it to me and asked if I could unlock her door. As I took the key and placed it in the lock I heard a sound from the parking lot. OH FUCK someone jumped in my car and was driving it away!!! In a flash I made sure Ronnie was supported by her room door and I immediately bolted for the parking lot. Nothing. My car was gone. What was I going to do? My phone was in the car. I was on a strange side of town and I was standing in the parking lot of some cheap motel.

Once the reality of the situation kicked in I walked back to Ronnie’s room. Half expecting her to be gone. Was it a set up??? Anyway she was still leaning against her door frame. “I am so sorry Hon” is all she said. I grumbled to myself and approached her. I didn’t say anything . I just stood next to her waiting for her to put her arm around my neck so I could help her inside. Without say a word she gained her balance on one foot and held on to my shoulder. I thought it was odd that she only used my shoulder for balance, but after what had just happened to my car I just wanted to get her inside and then decide what I was going to do.

I walked her into the room and carefully led her to the bed. She let go of me and gingerly sat on the edge of the bed. Once she was seated I looked around. She had the bed of course, a small table, a couch and a small kitchen. “Thanks for your help Hon” she said. I looked at her and said nothing. “Listen Tommy…can I call you Tommy?” I hated that name. I am 17 and my name is Tom I thought to myself. I shrugged and she continued. “Tommy can you help me over to the couch? I need to sit down, but I need to get this foot elevated.” I said sure and kneeled down. This time she wrapped her arm around my neck and waited for me to lift her. We slowly made our way to the couch and I let her sit. I took a pillow from the bed and placed it on the coffee table so she could elevate her foot. It looked a little swollen, but nothing too drastic. Would you like a beer Sweetie?” she asked. I hesitated. I had only had a sip of my Dads beer once. It didn’t taste very good, but I didn’t want to seem like some silly kid. “Sure I said a cold beer would be great”. She started to get up and the she remembered her foot. “I’m sorry Sugar, but can you grab you a beer from the refrigerator”? Oh and while your over there can you grab me one too?” I stood and walked to the little refrigerator. I opened the door and grabbed two beers. One thing I noticed about the room is that it was really clean. The motel itself was an old dump, but Ronnie’s room was organized and very well taken care of. “Bring me that beer Hon. I am thirsty” she said. With that I handed her the beer and just stood there. She popped I open, took a large drink and then looked at me for what seemed like forever. “Don’t just stand there” she said. She patted the seat next to her and said “sit here next to me Tommy”. I sat down.

I popped opened my beer and took a sip. I noticed her staring at me so I took another drink. This time a good sized gulp. I almost spit it back out, but I didn’t want to appear like a child. “Umm that is good” I said. “So you like beer do you?” she asked. I shook my head yes as I took another big drink. Before I knew it I had emptied the can. “Go get yourself another one” she said. I stood, feeling a little weird and walked to the fridge. I grabbed a beer. This time I did not wait for an invitation. I returned to the couch and sat right next to Ronnie.

I sat next to her. Beer in between my thighs and both hands on my beer. I stared straight ahead. Suddenly Ronnie spoke up. “Hon can you help me get out of this jacket?” “Sure” I replied. I placed my beer on the coffee table and turned to help her. She pulled her arms from the sleeves and handed me the jacket. “Just toss it on the arm of the couch Hon” she suggested. I did as she asked. She turned toward me and said “Thank you Tom and I am so sorry” I said “for what?” She went on to tell me how much she appreciated me helping her and how bad she felt about my car. My CAR!!! I almost forgot. I asked her if I could use her phone. She said sure and grabbed a phone from her purse. I took it and started to dial Mike’s number. “Crap” I thought to myself. With cell phones you didn’t have to remember phone numbers. After some deep thought I recalled his number and dialed. Voicemail damnit! I left a message and told him to call the number that I was calling from. I told him I would explain everything when he called me back.

“Your friend not available?” Ronnie asked. “Nope just had to leave a message.” I replied. I reached for my beer from the coffee table and just as I was taking another drink Ronnie accidentally bumped my arm and the entire contents of the beer fell into my lap. Holy shit I was having a sucky day. I stood up and tried to keep the beer from soaking my crotch. Too late. “Crap” I said out loud. “Oh Hon I am so sorry. I have been such a clutz today” Ronnie said. She told me to go to the bathroom and take off my pants and hang them from the shower rod to dry. Honestly I had two thoughts. I had not noticed the door she was pointing to earlier AND what was I going to cover myself up with? Like she read my mind Ronnie told after I took my jeans and under wear off that I could use one of the clean towels located under the sink to wrap myself with. I had not thought about leaving my underwear in the bathroom, but after she mentioned I agreed it was a good idea. They were as soaked as my jeans and they would not dry very well if I kept them on.
I walked to the closed door she pointed to, opened it and walked in. Like the rest of her room the bathroom was very clean. The plumbing fixtures were old, but the sink was spotless, the towels were bright white and bath tub looked brand new. I closed and locked the door. A little silly I suppose? She was on the couch with her swollen ankle resting on a pillow. What was she going to do right? Anyway I unzipped my jeans and pulled them down along with my boxers. I slipped them off and hung them from the shower curtain rod. My dick was cold. The beer literally soaked me to the skin. I looked under the sink and grabbed a towel. I took a quick piss and wrapped the towel around me. I opened the door and went through the door.

As I left the bathroom I could feel Ronnie’s gaze. Nothing creepy. Just her lifting her head and looking at me as I approached the couch. For an instance I thought about sitting in one of the chairs at her small dining table, but as if reading my mind she patted the couch and told me to sit next to her. I walked over and making sure my crotch was covered I started to sit down. “Oh wait” she said. Could you get us a couple more beers?” Without saying a word I turned and went to the fridge. After spilling the beer on myself I had lost the little buzz that I had, but went ahead and grabbed two more brews. I went back to the couch and sat down. I handed her a beer and opened mine. I am not sure why, but I tilted my head back and drank the entire can. I placed the empty can on the coffee table and got cold chills all over. I had goose bumps, but my insides felt warm. I put my hands over my crotch. Nothing was showing, but I had never been in only a towel with anyone. Especially not a grown woman. Suddenly Ronnie placed her hand on my knee. I froze. I did not know what to do. She started to rub my knee cap and slowly started to move her hand higher. She had two fingers under the towel and stopped moving her hand. “Tom” she said. “It’s getting hot in here.” At that she removed her hand from my thigh and started to unbutton her shirt. She quickly had all of the buttons undone and opened up her blouse. As I mentioned earlier she was a thin lady with a nice butt and long legs, but her boobs were very small. At this moment I could not care less. I had a towel wrapped around my naked torso and a grown woman with her shirt now completely off. Her bra was black and I could see the little bit of cleavage that she had. Before I knew it she reached behind her back and unclasped her bra. The bra fell away and she was sitting there on the couch in her dark skirt and nothing else. Her tits were absolutely gorgeous. Little globes of white flesh with huge areola and nipple the size of pencil erasers. She must have been cold because they were pointing straight out. “Hey Hon” Ronnie whispered. “Could you do me a favor and take a sip of my beer”? “Sure” I stuttered. She grabbed her can of beer from the little table next to the couch and handed it to me. “Tom I have one more request” she said quietly. “After you take a sip of beer would you suck on my nipple?” Holy Shit I thought to myself. Without saying another word I took a huge swig of beer, placed the can on the coffee table and very timidly leaned over and took her nipple into my mouth. “Oh that feels so cold and warm Tommy”. She hissed. “Twirl your tongue around it and then suck it baby” she instructed. I did as I was told. This was my first time with a girl, lady that is and I was nervous, but oh so very happy. I was really into it and I enjoyed Ronnie’s little noises she was making.

I continued licking and sucking. Alternating between her nice small tits. Suddenly I realized something. My cock had become hard and the towel had fallen to the floor. I was so entranced sucking her nipples that my initial embarrassment was not as bad as it would have been. Al l these first time experiences were overwhelming. No one other the guys in the gym shower had seen my dick. NO one had seen it hard. I looked up to see if Ronnie was paying any attention. Oh shit she was staring straight at it. “Why don’t you stop sucking my tits or a second and lay back and relax” she said. I took her advice. Almost as soon as I lay back to relax she took my dick in her hand. Slowly she stroked it. Just like I do when I am horny. The next thing I knew she kissed the head. I was harder than at any other time in my life thus far. After kissing it a couple of more times she opened her mouth and slid it in. OH God it felt like nothing I had ever felt before. She stroked it with her right hand and she sucked it. With her other hand she grabbed my ball sack and gently massaged them. I knew I was not going to last much longer. I said “Ronnie?” “Yes Tommy what is it she said as my dick was in her mouth.” “You better stop that” I said. “Why Hon” she asked. Than went back to blowing. “I’m going to cum Ronnie” She didn’t say a word. As a matter of fact she started sucking me harder. I was raising my hips and sticking my cock deeper into her mouth. She was pumping the base of my dick with her hand as she was aggressively sucking my knob. Suddenly I felt that familiar rush when you know you are going to cum. I don’t know what made me do it, but I turned my head and glanced over at Ronnie. I could not believe my eyes. Her skirt was lifted above her thighs and her hand buried deep into her cunt. Here was a grown woman masturbating herself as her mouth was on my cock. That was it. I could not take anymore. I watched her stick three fingers into pussy as I shot my thick white cum into her mouth. I swear I blacked out for a second. I was pumping my dick into her mouth and she was drinking rope after rope of sperm.

After I finished cumming and my breathing started to settle down I was able to lean back and relax. I had my arm resting on Ronnie’s back as she continued to finger herself and licking my dick. Making sure she cleaned up every bit of jizz. As she finished she simply stood up and let her skirt fall to the floor. There standing in front of me was a beautiful naked older woman. The hair on her pussy turned me on so much. She only stood there for a moment before stepping in front of me and slowly grabbed my cock. “I love how fast you young’ un’s can get hard so quickly after coming” she stated matter of factly. Once she had me hard she bent over and licked my dick a couple of times. The she did something that I will remember for the rest of my life. She turned around, shook her little ass and then sat down on my prick. Oh shit I was in heaven. Having my dick sucked felt like the best feeling in the world, but have a nice, hairy wet pussy on your cock is indescribable. I didn’t know what to do, but I knew I was fucking a woman and I wasn’t going to miss this opportunity. I spread my legs a little so she could go as deep as possible. She was mumbling to herself so I just placed my hands on her hips and let her ride me. She was not only going up and down, but she was rolling her hips as well. The sensation was out of this world. Her pussy was so wet I could feel her juices running down my balls. Just as I was getting into the motion she stood and said something I will never forget. She said “Tom I am going to get on the couch and put my butt in the air…will you be a Sweetheart and put that nice, young 17 year old cock in my asshole?” Just like that she had put her hands and knees on the couch and sure enough had that nice 55year old skinny ass sticking up. Thank goodness her pussy left so much juice on my cock because when I first placed the head of my dick against her poop hole I was met with resistance. But “good ole”Ronnie reached behind her and spread those ass cheeks open for me. I was rock hard and slowly entered her asshole. She told me to take it slow at first, but once I was completely inside she told me to fuck her hard. I didn’t need to be old twice. I grabbed her hips and started ramming my cock in and out of that sweet sphincter. She told me to reach around and grab her tits. The she told me to finger her cunt. She could not decide and she was uncontrollable. My balls were boiling and I was getting ready to cum. Just as I was about to announce the arrival of my eruption Ronnie interrupted my thought by screaming “I’m cumming Tommy Boy…I am so cumming? Fuck that tiny asshole Tommy Boy” I couldn’t take it any longer. I humped her two or three more times before letting go of the most cum I have ever felt in my life. I just kept spurting rope after rope of hot sticky sperm into her tight rose bud. I couldn’t take it any longer. I pulled out and collapsed on the couch. I closed my eyes and just sat there. Suddenly I heard Ronnie say something. “Open your eyes Hon” On command I slowly opened my eyes. I saw the most amazing thing I had seen in my short 17 years on this planet. Ronnie had remained bent over and she had a hand on each ass cheek. She was spreading her ass wide open and her butt hole was leaking my cum. It was streaming down to her pussy and then dripping onto the floor. I was in total awe. I had never seen anything so incredibly nasty, but oh so hot.

As I got dressed I heard a knock on the door. Ronnie asked me if I would answer it. I walked to the door and opened. There stood my friend Mike with a shit eating grin on his face. I looked past him and there was my beloved Cutlass Supreme. Mike said “HI” to Ronnie and gave her a big thumbs up!!! Let’s get out of here “Thomas”.

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