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Mom's Friend Dolly is a Great Teacher!

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3 likes 1956 views Category: Masturbation Male-Female Tags: oral, fuck, blow job, shower


I love to read the Solo board and stroke my cock. The stories are so exciting. I want to share an experience I had two years ago when I was 18 and a senior in high school.
My dad was going on an out of town trip because of his work and mom decided to go with him. Although I was 18 they did not want me to stay home by myself. I had thoughts of having a great party but they must have known. Since they were going to be gone 3-4 days they decided I could stay with mom's best friend Dolly. I wasn't too happy with the decision but I didn't have much choice and I couldn't go with them because I had basketball practice. Mom told me I must go by what Dolly's rules were and I agreed.
Dolly has know my mom since grade school and they have always been close friends. She seemed like an aunt to me even though she wasn't. Dolly had been divorced for the past two years and she had spent even more time with my mom. The first day my parents were gone I went to Dolly's after practice and she showed me where to put my clothes and where I would be sleeping. She just lived across town so going by my house for more clothes would be no problem.
Dolly had prepared dinner and we talked as we ate together. I had not really noticed before what beautiful blue eyes Dolly had and how she had a nice body. Dolly was wearing a pair of shorts and a t-shirt and she smelt wonderful. She patted me on the shoulder as she walked by telling me she hoped she could take good care of me that week. Little did I know Dolly would take GREAT care of me.
As I was taking a shower that night I felt the door open and Dolly told me she was laying out a towel for me to dry off with. I was surprised when she began to ask me questions about school and girls instead of leaving the bathroom. I didn't think too much about it and as I stepped out of the shower she handed me the towel and began to help me dry my shoulders. Her touch and her presence caused me to get a hard on and I had my back to her. When I looked in the mirror however I could tell Dolly was getting a look at my hard cock in the mirror. As I finished drying off Dolly sat down and continued talking to me as I put the towel around my waist and brushed my teeth. Even though having her in the room turned me on I didn't think a lot about it. My cock however did not forget and I had a raging hard on. As Dolly walked behind me to close the shower curtains my towel fell off and Dolly immediately picked it up and hung it on a towel rack leaving me naked and erect. Dolly reached around my waist and began to massage my balls and told me she didn't know how such a young boy could have such a big cock. She then started stroking my shaft up and down and kissing me on my neck. Dolly asked me if I wanted to 'blow off some steam' and I told her yes. Dolly's hands were so soft and seeing her red fingernails and her small sexy hands wrapped around my hard throbbing cock was exciting. Dolly turned me around and began to jack me off right in front of her face as she kneeled in front of me. I hoped she might suck on my cock but her hand job was also getting me off. As she felt me get harder Dolly took off her t-shirt and began to rub my hard cock on her lovely tits. Her skin was so soft and her tits were so sexy I knew I was going to come. She stroked me harder and told me to come on her tits. I felt my orgasm build and I shot my hot creamy load all over her tits and on her neck. She continued to stroke me and then licked the head of my last drop of come. Just as quickly as she started Dolly got up and walked away taking some kleenex to wipe my come off her tits. I was still standing there amazed and I decided to go to my room and get dressed. As I went back downstairs Dolly was watching TV and I sat in the living room with her. Dolly just talked and talked and never acted like anything happened between us. I was surprised she would be so calm after just jacking me off a few minutes earlier.
Not quite knowing what to expect I went to bed that night. When I woke up the next morning Dolly was getting ready for work as I was getting ready for school. While I was sitting in class I found myself day-dreaming of Dolly's great handjob and I wondered if I should be more aggressive with her. When I got to her house that afternoon after practice Dolly again had supper ready and talked and talked to me at the dinner table while looking straight into my eyes. After we finished eating Dolly asked me to help her with the dishes and as I was helping her she continued to rub against me often brushing her ass against my jeans. If she was trying to get me hard it worked! As we finished the dishes Dolly began to rub my cock through my jeans and she asked me if my hard on was for her. I laughed and said of course and she slowly unzipped my jeans and began to gently bite on my now hard cock through my underwear. Dolly also continued to rub my growing cock through my underwear and told me she had forgotten how big and sexy it could be. When she pulled my underwear down off my waist my cock sprung up in front of her face and she immediately began to lick the shaft working her way up to the shaft. Dolly was tickling the sensitive underside with her tongue and my cock just bobbed up and down in front of her as she laughed. Dolly then put both hands around my shaft and bent it down so she could put her lips around it. I had never had a blowjob before and Dolly seemed to be an expert. Dolly worked my cock in and out of her mouth and by now my erect cock was covered with a sexy coating of her spit. Dolly began to make loud slurping noises as she sucked me even harder and I was trying like hell not to come too fast. Dolly took my cock out of her mouth and began to stoke it up and down. 'I think it's bigger today than it was yesterday' she stated while jacking me off. Just as she did the night before her sexy hands were getting me off and I told her I was going to come. Dolly told me she wouldn't swallow but I could shoot my load on her face. I was so damn excited I thought I might shoot my load on the walls and the ceiling! Dolly ran her tongue under the head of my cock as she was stroking me and I began to come all over her face. My first two strands landed on her forehead and her hair and then I came a bunch more on her sexy cheeks and in her mouth. Looking down at Dolly and seeing her sexy red lips wrapped around my cock and my hot creamy come all over her face was a sight to behold. She was not in any hurry and she rubbed my cock on her lips as I looked at her come soaked face. Dolly got up again and cleaned herself up and again never said anything the rest of the night. She wasn't mad or upset with me she just acted like nothing happened.
The next day in school I found my cock getting hard as I thought about her handjob and her wonderful sloppy blowjob. What also puzzled me was how she just stopped when I came and then acted like nothing different had happened.
As we were eating dinner the next night Dolly and I talked as we had done each night. I had hoped she would want to get me off again this night but she never made any moves. As we were talking she excused herself from the TV room and went to take a shower. I had thoughts of helping her 'dry off' like she helped me but I was concerned I would be to aggressive. After I took my shower Dolly did not come in as I had hoped and I returned to the TV room. Dolly had on a sexy blue teddy covered by a white robe. As she was flipping through TV stations I asked Dolly if she enjoyed herself with me the last two nights. Dolly began to cry and sob and I was afraid I had said something wrong. As I went over to her and sat on the couch with her she put her head on my shoulder sobbing. As I stroked her hair and hugged her she told me she felt guilty for 'taking advantage' of me and this situation. As I continued to stroke her hair I told her she had NOT taken advantage of me and on the contrary she had helped me see how a woman could please a man. She continued to cry and told me the last 5 years she was married to her ex-husband he had not had sex with her and instead had a series of affairs. Dolly cried and told me she thought she was not 'sexy enough'. I told her she was a very sexy woman and my hard on should have showed her that. She laughed and told me I talked to her like her ex-husband never did and I seemed to value her opinion. I reached over and gave Dolly a very slow french kiss and worked my way down to her sexy neck and shoulders. I had never had the chance to please a girl/woman this way and my heart was beating out of my chest. As I opened her robe and began to slowly squeeze her tits Dolly moaned and groaned. I then got on my knees on the floor in front of Dolly while sucking on her great tits and teasing her nipples with my tongue. I worked my way down and began to run my tongue in and out of her belly button. I wanted to suck on Dolly's pussy next but I had never done this before and wondered how I would know what to do. As I began to slowly kiss her inner thighs I stuck two fingers in her pussy and Dolly was wet and ready. As I made my way over to her pussy I was surprised to see that she had a shaved pussy with just a triangle of pubic hair at the top of her clit. Her pussy lips seemed bigger and more swollen than I expected but whereas my buddies always told me that pussy had a nasty smell, Dolly's pussy tasted and smelt sweet. Dolly grabbed the back of my head and began to raise her hips into my face while telling me what to do. She moaned and told me to suck the lips separately and as I did and stretched them out gently she was coming all over my face. When I started to tongue her clit as fast as I could she again grabbed the back of me head and told me not to stop. I swear Dolly must have come over 10 times that night and my first lesson in eating pussy was a very educational one.
The next evening when I got back to Dolly's from school and basketball practice my mind was racing about my 'sexual education from my teacher'. Dolly and I talked at the dinner table and she began to cry again. When I asked her what was wrong. She kept crying but told me she always thought her pussy was 'dirty' because her ex-husband never gave her any oral sex. She told me she was crying because she was happy to have these few days with me because I had built up her self confidence so much. She told me she hoped I wasn't 'damaged' by her sexual aggressiveness and I joked with her if this was what 'damage' felt like she could hurt me anytime! Dolly laughed and told me I had talked to her more and made her feel special more in these few days than her ex-husband or anyone else she had dated. I told her I was glad to spend time with her and I thought she was a great 'teacher'. Dolly laughed and told me I was a great guy.
As I went to bed that night I went to Dolly's room to tell her good night. Dolly looked so sweet and so sexy that night that as I kissed her good night I asked her if I could share her bed since I was going home the next day. She told me she was glad I asked because she was thinking the same thing. Dolly had on her sexy silk blue teddy and as I laid down next to her she asked if she could rub my shoulders. I told her yes and she began give me a great back rub. After a few minutes she leaned over and began to kiss me on the neck and nibble on my ears. She asked if I wanted my 'teacher' to give me 'one more lesson' and I told her I thought she would never ask. Dolly laughed and rolled me onto my back and got on top of me. She then reached down and took off my underwear and I felt my cock spring to action. Dolly began to slowly rub my cock against her pussy while she was sitting on top of me. It was so sexy to have her warm naked body rubbing against mine that I began to move my hips toward her. When Dolly picked up her hips and slipped my hard cock into her wet pussy for the first time I could not believe how wet and warm her pussy was. It was the first pussy I had ever slid my cock in and it was unforgettable. As Dolly started to ride up and down on my cock I could not believe how her pussy lips grabbed a hold of my throbbing cock and squeeze me. Dolly began to moan and I reached up and gently kneaded her great tits and pinch her nipples. Seeing Dolly ride up and down on my cock was the sexiest thing I had ever seen. Seeing my cock slip in and out of her shaved pussy was getting me off way to soon. I told Dolly she was making me come to fast and she quit riding me up and down and just leaned forward and held me tight while my cock stayed deep inside her pussy. She whispered in my ear that she could hold me forever as long as I promised to keep my hard cock in her wet pussy. I asked Dolly if I could get on top and she told me yes. As I turned her over I kept my cock inside of her. As Dolly spread her legs and gave me complete access to her sweet pussy my cock went deeper and deeper in her pussy. I felt like I was splitting her in half but she wrapped her legs around my lower back and thrusted back against me. Dolly told me to fuck her harder and faster and I pulled my body up in a push up position which only left me touching her pussy with my hard cock in and out. This was so sexy that I continued to thrust harder and harder as I felt her come. I told Dolly I couldn't last much longer and she told me to come deep in her pussy. As I then spread her legs and held her ankles with my hands I had the greatest angle I ever had as I plunged my hard cock in and out of her sweet pussy. I began to spurt my load deep inside of Dolly and I could feel her come with me. Even though I was drenched in sweat Dolly pulled me down on top of me and we laid together before getting under the sheets. Dolly wiggled over in front of me until my body was right behind her and I wrapped my arms around her. The next morning as we woke up Dolly reached back and began to stroke my cock which got hard immediately. She whispered to me that she wanted me to 'take her from behind'. As Dolly got up on all fours her sexy ass was right in front of me and I slowly rubbed my cock against her pussy lips. As I slid my cock in her slowly I couldn't believe how different this felt than last night when I fucked her so well. I grabbed Dolly's hips and thrust her back toward me as I rammed my cock in her pussy from behind and she squealed with delight. Dolly admitted to me this was her 'favorite position' and she loved how deep she could feel my cock going. Dolly told me I was a great lover and that she loved being my 'teacher' this week. I told Dolly I could not have learned from a better woman and her sexy body caused me to get so many erections. She laughed and told me she loved to 'feel sexy' and that I was the one who helped her feel this way. As I began to gently spank Dolly on the ass as I was fucking her slowly from behind I felt her come again and again. I had to agree with Dolly that this was one of my favorite positions too as I felt totally in control and I loved to see her sexy ass right in front of me and her sexy tits bouncing up and down with each stroke. I told Dolly I was going to come and she told me to come deep in her pussy. As I shot my load deep inside her it felt just as strong and just as good as the load I gave her the night before.
When my parents got home they told me they hoped I wasn't too bored spending time with Dolly and I told them we found we had a lot in common. Dolly told my mom that I was a real gentleman and that she really 'enjoyed my company' as she winked at me. Even though I never had another chance to get back together with Dolly the lessons she taught me have gone along way in my ability to please a woman today. What a teacher she was!!



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