I was twenty seven and had been in a rehabilitation program for two years. It was an experimental program, and we had people in the field visit us to see what we were doing and how we did it. We had Judges, parole and probation officers, and even people from other programs. I was the public relations person for the foundation.
One day, my boss introduced me to a probation officer from the southern part of the state; we were up north. She was short and thin, with shoulder length brown hair and hazel eyes. She looked to be about forty five years old. She wasn't a beauty, but she wasn't unattractive either. She was going to spend two weeks studying the program. She also would be joining in to observe our group therapy sessions. I was to "baby sit" her while she was visiting.
She was fun to talk with, and we got along right away. After a couple of days spending time together, she became a little more friendly and would sit close to me and when she sat, she'd cross and uncross her legs or run her hands slowly along her thighs. It seemed she was constantly drawing my attention to her legs. They were her best asset.
One afternoon we needed to go to another one of our buildings across town. She offered to drive. I sat in the passenger seat, and she climbed into the driver's seat. As she sat behind the wheel, her skirt rode up on her legs. I could see the darker top of her nylon stockings. My eyes were fixed on her lovely thighs. She had a stick shift and after shifting gears, she'd rest her hand on her right thigh.
She had never said anything or made any overt moves, but she was starting to get me hot under the collar. My cock grew hard in my pants. She let her legs spread apart as she drove so that there was a wide gap between them. I was wishing I had the nerve to reach my hand over and touch her thigh. I thought better of the idea, and I did not act on my impulses.
That night we attended one of the encounter sessions. In these groups, we were allowed to say anything. There were two rules, no walking out while in the "hot" seat and no violence or threats of violence. As we moved around the room, residents talked about their stuff, whatever it was. Then there was a couple in the group who had a love relationship going on, and they talked, yelled, screamed and cried about their personal issues.
Then it was the probation officer's turn to be in the hot seat. After we all talked for awhile with her, she said, "Is it true I can say anything and it stays in the group?"
We assured her that was the case.
She turned to face me. Looking in my eyes she said, "I like you. I mean that I really like you."
"Ha, ha," one member of the group laughed. "Sounds like your probation officer wants to fuck you!"
I was used to the game, but this remark made me blush.
"Is that true officer?" another person asked. "Do you want to fuck one of our bad boys?"
"Well, if you want to be crude, yes I do. But I don't know what the rules are concerning that," she answered.
Another member joined in, "We don't have rules about fucking! It's not a wrestling match. There's no fuckin' score keeper."
"Do you fuck the men you have on your case load?" a woman asked.
"No, of course not." she said.
"You're old enough to be his mother for crying out load. What are you, some kind of pervert?" yet another asked her.
I was too embarrassed to join in and was hoping they'd stay off of me. After some more probing, and joking, the group explained to her that after someone has been in the program over eighteen months, sexual and relationship issues are up to the two involved.
"So, yeah lady, if he wants to fuck you, he can. He just needs to come back and give us details," another guy says. Then he threw up his hands towards me, "JUST KIDDING! Just screwing around."
Another said, "No, that's what they're going to do, screw around."
After the game, we would gather in the dining room for coffee and cigarettes. We were standing at the bar. This building used to be a hotel with restaurant and lounge. We used it for residency and as a club house. As we stood close to one another, I asked if she'd like to take me with her that night.
When we were situated in her car, I reached over and placed my hand on her thigh. I placed my left hand behind her head, and I leaned in to kiss her. She kissed frantically, as though she'd been starved. Then I felt her hand between my legs and rubbing across the hard bulge in my pants. I was eager for her.
As soon as we closed her motel room door, she was in my arms and we were deeply kissing. I ran my hands across her ass as we embraced. Her hand unzipped my pants and then her fingers crept inside and found my stiff manhood.
She pulled it out of my pants and began jacking me slowly. Then she did something I'd never felt before. She took the tips of her fingernails and lightly ran them along the length of my staff. Back and forth she did this. It felt fantastic and made me harder. I began unbuttoning her blouse so I could get to her small breasts.
When we took a break for air, she whispered in my ear, "I've wanted you from the minute I met you. I knew I was in trouble."
"Yes," I whispered back. "You are in trouble you naughty officer you."
We both undressed and climbed onto the bed. I went down between her legs and began kissing her wonderful thighs. I kissed the soft white flesh around her womanhood. Then I began licking her between the legs. She had a healthy dark bush there. Her hairs became drippy wet with my saliva as I licked on her.
I felt her body tense as my tongue divided her pussy lips so my tongue could slip inside of her. As I slowly licked her, her body relaxed, her legs opened wider and I began feasting on her goody box. I licked inside her and my tongue explored everywhere. Finding her clit, I began flicking it with my tongue tip and then sucking it up into my mouth and running my tongue over it as I sucked on it as well.
I became more excited as I heard her moaning as I pleasured her. Her fists were clutching the bed sheet as she raised her ass off the bed, pushing her crotch up into my face. I was determined to suck her to orgasm before I'd enter inside of her. I licked her, sucked her, kissed between her legs and fondled her breasts as I did.
I heard her gasping and felt her quake as I was bringing her to climax. I let her fill my mouth with her cum. I swallowed the nectar and then rose up from her nether region and climbed over her naked body so I was able to rub the tip of my burning cock along the slit between her legs. Giving more pressure, I forced my rod between her love lips and slid my cock inside of her for the first time.
She felt like heaven. So wet and warm and so willing to have me inside of her. I was rotating my hips as I would thrust myself inside her. She threw her legs up into the air as I rode her. Oh my God was I enjoying her. Here we were, separated by age and everyone knowing what we were now doing. This turned me on even more to know they knew I was fucking this older officer of the courts. I was still on probation from my county while I fucked another county's officer. And I loved that she had literally asked for it.
I found her mouth with mine and we began kissing heavily as we fucked one another. Our tongues entering each other's mouths and dancing with one another. I began ramming her harder as I became more and more excited.
I could feel my excitement well up in my loins as I gave her my cock, again and again. Then I groaned loudly as I could hold back no longer, and I exploded and shot my cum inside of her. Fucking her until I was dry.
We were together two more times before she had to leave. To this day I wish I could see her again.
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