Chapter 7: My First Girlfriend with Strings Attached

It was a couple of days after Jenny’s check-up, and she was feeling much better. The bruises were fading, and her ribs, although still taped, were not causing her as much discomfort as before. I had just come in from working with Ted and Carl and needed a shower. I passed Jenny in the kitchen, said hi, and that I would be down once I cleaned up.

I went up the stairs to the upstairs bathroom and turned on the shower. I peeled off my sweaty clothes and dropped them on the floor. Stepping under the hot water, I let the heat soothe my aching back muscles.

I walked out of the bathroom naked, drying my hair with a towel as I headed to my bedroom for clean clothes. Then I heard, “My, my, don’t you clean up nicely.”

Quickly wrapping the towel around my waist, I looked at Jenny standing at the top of the stairs with her arms folded, smiling at me. Jenny often did light cleaning and picked up after two very sloppy men. I stammered, “What are you doing up here?”

“I was going to throw in a load of wash and just came up to get your dad’s and your dirty clothes. I suppose you left everything on the bathroom floor again.”

I just nodded as she went in and picked up my clothes from the floor, came back out and held out her hand to me, and asked for the only thing covering my privates, “Give me that towel. I will wash that too while I’m at it. I gripped the towel tighter and started backing up toward my room. Jenny had a devious smile on her face as she followed me into my room and shut the door. I kept backing up until the back of my legs hit the edge of the bed, and I was forced to sit down.

“Don’t be such a whoosh, John. Today is the second time I have seen what you have down there, so what’s the big deal?”

Jenny dropped the clothes she had in her hands and reached out to grab the top of the towel, and pulled. I gave up and let go of the corners I was holding together. Jenny flipped the towel aside. I went to stand up so she could pull the towel out from under me, but she put her hand on my shoulder and told me softly not to get up. Reaching down, she took my cock in her hand and told me what she wanted, “I want you to make love to me, John.”

The only protest I could come up with was, “What about your ribs?”

“You heard the doctor, they are healing nicely, and as long as you don’t kick me, it will be fine. Now get in bed.”

I pulled back the covers and got in bed. I watched as Jenny removed her blouse, bra, shoes, slacks, and panties and slipped into bed beside me. I have to admit I was utterly clueless and at a loss of what to do next. Sure, I fantasized about her, but I never expected this beautiful woman to crawl in bed with me. I was still under the impression that I was just helping out a friend in need until she could go back to work. As Jenny snuggled up to me, she told me she was tired of dropping hints and figured the direct approach was the only way she was going to get me in bed. Of course, I asked the dumb question that would have pissed off any other woman and sent them running from the room. “You’re not doing this as payment for me helping you out?”

Jenny put her arm over me, “I can understand how you might think that because of what I do to make a living. But let me assure you that is not the case. As I said, I want you to make love to me, not just have sex with me. I like you, John. I like you a lot more than you know. I know I am older than you, and what I do for a living does not make me a socially acceptable girlfriend. I hope you can see it in your heart to be the friend and lover I want you to be.”

“You said, girlfriend. You would want to be my girlfriend?” I asked hopefully, but Jenny was not through explaining what she had in mind.

“To me, being your girlfriend is a lot bigger commitment than friend and lover. You are already my friend, and I am asking you also to be my lover. Having you as my lover means that I will have sex with you just for the pure joy of being intimate with someone I deeply care for. However, we both will still have the freedom to live our life separately, keep secrets, make major decisions and even sleep with other partners without having to seek the approval of our lover. Being your girlfriend would turn all of that upside down. I need to tell you some things about me that will most likely make you change your mind about having me as a girlfriend.”

I started to argue, “I don’t think...”

“Please don’t interrupt John. I’m going to give it to you down and dirty, and if you want to argue with me or ask questions when I’m done, that will be okay, but not now. Who I am today all started when I discovered sex when I was a junior in high school, and I loved it. I started to have a lot of so-called boyfriends, and I had sex with all of them. By the time I was a senior, I had a reputation for being easy, and I did not care. The more boys that wanted to fuck me, the better I liked it. I even let the Kelly brothers take turns with me one night in the back seat of their car in the middle of my senior year. What one of them said to me changed my life. Pete Kelly was just getting off of me so his brother could have his turn when he said, ‘damn bro, she is so hot we should be paying her.’ After they dropped me off that night, all I could think about was what he said about getting paid to have sex. The next day in school, I cornered them in study hall and asked them if they really thought I could get paid to have sex with guys. The younger brother Tony laughed and said, “Jenny, I could line four guys up to fuck you in the next twenty minutes and get 25 bucks apiece from them. The Kelly brothers became my first pimps. I took care of them when they wanted to fuck, and they drove me around, and I made money in their back seat whenever I wanted to for the rest of my senior year.”

“That summer after I graduated, we branched out. The over twenty-one crowd had much more money than high school kids, and I started getting $100 or more a trick. On weekends I was pulling in $200 to $400 a night. Things would have worked out a lot differently for me if the Kelly boys and not gone off and left me to my own devices. Pete left for college at the end of that summer. Tony pimped for me through his senior year and the next summer until he joined the Air Force. About eight months ago, I decided to leave the small town and hit the big city to try my luck. I ended up in Hartford, and you pretty much know how that worked out.”

“What you need to know, John, is that I loved what I was doing when I was with the Kelly brothers. When I started making real money, they took a cut, but we’re not greedy and made sure the men I had sex with were not monsters or deviants. If I did not feel like working or only wanted to do one guy for the night, they were fine with it. I did not mind and even enjoyed having multiple clients for sex in the same night, and the money was good. If it was a slow night and I was feeling in the mood, I would take one or both of the Kelly brothers to bed to have that wonderful feeling between my legs.”