When I was younger I was always really into my friends mom; she was your perfect milf, she was probably in her mid 40s, very short petite woman with C sized breast with a slight sag. One night when I was sleeping over we started going through a bunch of old photos at there house. After about three quarters through my pile of photos I was looking through I came across a exciting surprise. It was a photo of my friends mom on top of a ski mountain topless with her small dark nipples visible through her see through bra! I was so turned on I immediately hid it in my waist band of my shorts so I could study it later on. Later that night I slept out in the living room and looking at her photo I stroked my throbbing cock over and over until I finally fell asleep. Early the next morning I woke to my friends mom quietly cleaning the living room. I laid there pretending I was asleep whenever she would look in my direction. I was so hard and turned on while watching her/ fantasizing about her and all the things I wish I could do with her. I had to do something. While she was turned away I pulled my young hard cock out the side of my shorts, rolled over on my back letting the covers fall to the side so my exposed cock was standing straight up in plain view for her and I waited pretending to be sound asleep. It took her about a minute to finally notice. My hope was that she would come over and start rubbing my cock or wrap her sweet lips around the tip such as you see in the porn videos. It wasnt quite what I hoped for, probably because at the time she was still married and your typical family mom. But later I would find out she definitely had some naughty thoughts and fantasies of her own. When she finally turned around and saw my young cock fully exposed, I heard her quietly gasp and say to her self "oh my god" she then sat down across from me for about 10 mins. I'm not sure what she was doing since I had to act asleep. Eventually she came over with another blanket. . Standing over me and being so close to my cock I nearly lost it and came as she put the blanket over me. Thinking back now, I wish I would have lost it and made a mess right in front of her!
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Friends Mom. True Confession
Fast forward 4 years. My buddy and I were both back in our home town for break. At this point my friends mom had gotten divorced and was now managing a bar in a small tourist town near by. We decided to go up to the bar, we were 20 but she told us we would be fine there and we can crash at her condo. We drank quite a bit that night and eventually we closed down the bar that night with her. Once we got to her condo my friend immediately went to the bedroom and was out of it. That left me and his mom up alone visiting and watching tv. As I was scrolling through the channels I turned on taxi cab confessions. That led to some joking and I felt like she was flirting with me. At that point I decided to just go for it. I told her that I wanted to make a confession. She said alright and asked me what my was.. I said, Katie, I've always had a thing for you and thought you were very attractive. She blushed said thank you and then told me she has always thought I was very handsome too. Since I had a lot of liquid courage in me i then came right out with it. I asked, Katie about four years ago I stayed at your house and in the morning do you remember anything about me? Well I did that on purpose. She was very surprised and asked, you really thought about me that way all the way back then. I replied with a nod and smile and told her I still do and it's on my mind right now. Katie then put her hand inside my thigh and told me she loved what she saw the first time and would love to see even more. I leaned over and then started kissing my friends mom, I couldn't believe that it was happening. While kissing her I lifted her shirt off for her and then her bra. There were those beautiful dark nipples right in front of me this time! I then stood up right in front of her and stripped Down to nothing. When I took my boxers off my cock just sprung out like a spring I was so hard. Katie then told me how much she had thought of my big cock throughout the years and wishing she would have made a move like I wanted her to four years ago. I sat back down next to her and she asked me to start masturbating for her, that she wants to see how I did it everytime I thought of her before. She pulled out some lotion out of her purse and covered her hand, she then wrapped her tiny little hands around my cock and with a few pumps up and down she had my cock all lubed up. She then told me to take over and show her. I began stroking my cock for her, having her right there watching me and talking dirty to me was incredibly hot. After about 15 mins of masturbating she then laid down on her back and told me to straddle her, that she wants my cock in between her breasts! Once again I couldn't believe this was happening to me. Specially with my friend past out drunk in the back room. Before I got on top of her I unbuttoned her jeans and slid them to her knees. I then got on top of her; while she pushed her breasts together I slid my cock in between slowly up to her lips, when her tongue touched the tip I just about lost it. I then reached back and slid my hand down the front of her black panties and started rubbing the top of her warm pussy while I slid in and out of her breasts. After awhile I was aching to be inside her. I pulled my cock out from between her breasts and leaned further forward and sunk my cock deep in her mouth and held it there till she got me super wet. I then pulled out and moved down her body. I pulled her black panties off the rest of the way, lifted her legs and slid my cock deep inside her wet pussy. Thrusting in and out of her I could feel myself getting close to climaxing, before I even had time to ask her where she wanted me to cum, her pussy squeezed tight while restraining herself from moaning to load and I released my warm cum deep in my friends mom.
After, we just laid there for a bit still inside her talking about how great that was and also about how we need to keep our experience between us. Eventually Katie went to her room while I feel asleep on the couch. The next morning I was a little uneasy hoping that my friend hadn't heard anything. We rode back that day and he hadn't suspected a thing.