My First Older Woman. (First Time) (Anal cum) (Gap
I was a pretty good k** growing up. Didnt get into a lot of trouble at school, went to church every sunday and was even trusted to baby sit some of the k**s from church. One of the ladies I baby sat for was Annie, she had married the pastors son. They had three k**s and both had to work, so I baby sat for them frequently. Annie was a beautiful woman part asian and part hispanic at about 5'9", dark black hair, ivory skin, DD chest and a very curvy figure. I was in my teens when I was babysitting for her and would notice her looks every time I came over. It was hard not to. But she was related to the pastor and I watched her k**s so I tried to ignore the lust I had for her. It was pretty hard to do though as she was involved with the youth group so even when I wasnt baby sitting I spent a lot of time around her. Seeing her in a bikini, or doing thing like tying a cherry stem into a knot with her tongue....most of the boys in youth group were turned on by her.
Well as the years past a lot of things changed. I moved out of town to go to college and she wound up divorced from her husband. Anytime I would go back home I would call to see what she was up to and she was usually out clubbing or something. I was only 19 and couldnt get into most of the clubs she was going to. Well one wednesday afternoon I got a call from her asking if I would be willing to come to town to watch her k**s while she hosted a party at a hotel for her boss and his company. She was his secretary so she was charged with setting up the entire party. Her exhusband was being a bit of a jerk and wouldnt take the k**s for the weekend so she just decided she had to get a room at the same hotel and have someone watch the k**s. I agreed to do it, if anything at least I would get to see her!
Well that Friday I drove back home and the party would be Saturday evening. I spent time with my f****y in my old neighborhood friday night and saturday during the day. But Saturday afternoon with a bag packed I headed to Annie's house. She explained the situation and that I would be able to be paid Sunday morning after her boss paid her. So we packed up the three k**s and off we went to the hotel. She had to set up for the party in the ballroom. I spent time with the k**s in the pool, as well as an arcade that they had on the first floor of the hotel. We all went to dinner at McDonalds so the k**s could play before we were stuck in a hotel room for the rest of the night.
The evening rolled around and Annie had to prepare for the party. She came out of the bathroom looking sexy as hell. A form fitting black dress that plunged to show an amazing cleavage line and her curves. The dress stopped about mid thigh showing her amazingly firm legs. She kissed the k**s, gave me a hug while saying thank you and went on her way.
Not even an hour had gone by when there was a knock at the door. It was Annie and a coworker who had snuck up to tell me that Annie's oldest daugher Hillary was going a few rooms over to play with her coworkers daughter, and that her exhusband had called and was wanting his other two k**s. So the oldest daughter went up the hall to another room where her friend was and I was going to wait for the father. When he got there I handed off the k**s and just hung around the room I had ridden with Annie so I really didnt have anything else to do, and hadnt brought anything that I could really wear to a party.
I was standing out on the balcony that over looked the pool when I saw two young people come out poolside late at night. They looked like they were either at the party hosted by Annie or another one in the building. The scurried along looking all over the place until all at once they both stipped naked and jumped in the pool. The girl was amazingly sexy with red hair and a great body. I cant give too good of stats because of the position I was at, but I can say her body was amazing. Watching her swim back and forth my cock began to stiffen immediately. After a while the couple swan towards each other and embraced in a kiss. The kiss began to heat up and after a few minutes she was riding his cock at the side of the pool. I watched intently as I reached into my shorts and started stroking my rod. This was better than watching porn because it was real and it was right there.
As I wa stroking slowly and getting near my peak I heard a rather d***k voice next to me "what are you watching down there?" Annie said, luckily enough not noticing my hand in my pants.
I was startled and jumped..."Oh nothing much....just getting some air." I kept my back to her so she didnt see how tight my shorts were from the hard on.
She looked over my shoulder and saw the couple screwing in the pool "Oh wow...well that is quite a show isnt it! Bet that is better than television!" she giggled.
"Yeah I guess so," I said sheepishly.
Annie continued looking over my shoulder and snuck a peak downward "Well it looks like you are REALLY enjoying the show arent you Scott?" I was getting a mischevious grin from her now..
I was embarassed and didnt know what to say....so I said nothing. She grabbed my shoulders and turned me around, reached down and felt my cock through my shorts.
She leaned in next to my ear and moaned, making my dic twitch with excitement. "Why dont we go inside?" She said as she grabbed my hand and lead me inside.
As soon as the sliding glass door shut she was kissing my neck and sliding my shorts down until they fell to the floor with my member springing out toward her. "There has always been something about the way you watched me that turned me on Scott."
"You have been turning me on since highschool Annie." I said in return as my hands cupped her breasts from outside her dress. She slowly slid to her knees and began to lick my rock hard piece and all I could do was stare. She slowly took the tip in her mouth and began to cover every inch of me until my entire piece disapeared into her mouth. Slowly stroking my cock with her warm mouth while her free hand played with my sack I could already feel my young self getting close to cumming so I pulled my cock away from her and stood her up. I began kissing her deeply as I reached behind her and unzipped the little black dress and slid it to the floor. There she stood in a matching red and black lace bra and panty set with those huge tits just aching to be set free. It was the best sight I had ever seen, and can still picture it like it was yesterday.
I walked up to her, reached around and undid the bra letting it fall next to her. Her nipples were standing at attention as her beautiful breasts still sat up really nicely for her age. I began licking, biting and sucking her nipples while we inched closer to the bed. We got to the bed and she slowly sat down as I slid her panties off to reveal a nice looking pussy with a small trimmed patch of black hair above it. I began to salivate at the thought of tasting that sexy pussy that I had tried my hardest not to fantasize about for so long. I dove in like a swimmer in the olympics. Licking her pussy, which was already wet and sweet, while I used my thumb to play with her clit. She was moaning and writhing with pleasure and saying words I dont know that I had ever hear her say, which only drove me wilder. I moved onto the bed and got her to straddle my face so she could grind her pussy on my face as much as she wanted. We wound up in a 69 position rather quickly where we were both just frantically sucking and licking each other. I felt her pussy contract as juices flowed over my chin as she groaned in pleasure.
After she climaxed on my face she slid my cock deep into her in the reverse cowgirl position....I had held out for a long time without cumming and didnt know how long I would last. She hopped up and down agressively as her warm wet twat hugged my rod. I was thrusting up at her as she rode and could feel the build up in begin. As if she knew what was about to happen she said "Cum inside me Scott, do it."
Not True Story I am not author of this story.
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