Where it happened: The bedroom
Langauge: English
Sex: Male
Rating: 9
Category: Straight
I had just joined the Big Brothers program and was assigned the boy of a fairly wealthy woman. The first time I saw her I was in awe. She is 5’10” skinny, has beutiful blue eyes and small firm breasts.
Her boy was 9 and I had taken him bowling, golfing, and to several minor league baseball games. One day I showed up to take him to I football game on the usual schedualled day. when his mom (We’ll call her Susan) opened the door I asked for him.
“He’s not hear but I need your help with something upstairs. Can you help me?”, she said
I agreed and went up stairs she directed me toward her bedroom. When we got in there she quickly shut the door and started taking off her clothes almost franticly. I was stunned. Next thing I knew she was tugging at my belt, her tongue probing my mouth hungrily.
“I haven’t had sex since my son”, she whispered in my ear.
Half undressed she pushed me into the bed. By now I had figured out what was going on and was a willing partisipant. She kept saying “Kiss me” then covering my mouth before I could respond. Her body was hot, her hips rotated, “Do it. Oh, please do it”
Nervouse I entered her slowly. She made tiny peeps of pleasure each time. Soon her back arched and her tiny peeps becames loud moans. I knew she had come. Stunned at this beautiful thing I paused. “Don’t stop. Please don’t stop”
Upon hearing this I took control of her body thrusting with all my might. She rapped her legs around me and added to my efforts. We both came within thirty seconds of each other. First me then her. Spent we lay there beside each other.
Upon regaining my strength I rolled over on top of herand began kissing all over her and rubbing her tender breasts with my thumbs. “I’m getting hard again”, I said.
“Do you need any help?”, she asked.
“That would be great.”,I said.
Her slid out from under me and walked over to her dresser. She opened it up and pulled out some blue clothing and a pair of handcuffs. “I’ll be a minute”, she said. She walked into a small bathroom that was atached to the bedroom and closed the door. A few minutes later she opened the door and walked out. The blue clothing was a police uniform. She had her hair tied up and she walked over to me. She roughly grabbed my wrist and put the handcuffs on then she attached the handcuffs to the headboard. “I bought these the first day you took out michael”, she said. Then she began to strip just a few feet from me. After taking off her blouse leaving on her skirts and bra she walked over to me put her hand on my penis and said, “Looks like I’ve found a concealed weapon. Are you going to use it?” Then she took off her skirt and braw. She walked of and layed down between my legs and licked my penis. It began to throb and she pulled of her underwear, sat on top of me and began to hump me. She angled her body so that my penis grinded against the most sensitive part of her vagina. Both of us came quickly again.
Afterwords we never slept together again. Though we did start dating. When the people at the Big Brothers Club found out they reassigned me and eventually we broke up. I haven’t seen her since the breakup but I’ll never forget my first time thanks to her.
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