His Indecent Proposal: 7

Book:Crazy Pleasure (Erotica) Published:2025-2-5

I think as long as you love someone there is enough to talk about. But for Bobby and I, the longer we were apart the less we seemed to have to say to each other. I called Bobby the day after Tom and I had done the deed in my living room, and I felt weird about it, but I didn’t feel… bad. I didn’t feel guilty. Tom had seemed pretty business-like about the whole thing and when I saw him at the gym he pretended like he didn’t know me, or gave me the briefest of waves and went back to whatever he was doing.
I talked to Bobby and we went over his days, what he was studying, the jobs he was already interviewing for. I talked about my lame secretarial job and how I was trying to find a place.
“A place?” he said. “Weren’t you saving up for graduate school?”
I was but I wasn’t sure if I wanted to do that now – if I even could do that now. So it made more sense for me to do one thing at a time. I didn’t know if it was the right thing to do but I was going nuts trying to justify living at home with my parents when every day I was less sure I was an adult. So Bobby and I had a few things to argue about but we didn’t really have much in common. The next week was his midterms so we stopped talking altogether.
It was also nearing the day when I’d have to decide if I could follow through with Tom’s agreement. He said put myself on display and bring him a token.
You know, for about a week I was sure I wasn’t ever going to do that again. I’d let him pay me for sex, and that was weird, and kind of exciting in its way. Would I? Then the next week rolled around, and I didn’t want to call Bobby, and Allison had been going to the gym less since Sara got back in town. Mostly they wanted to smoke or hit the bars and, as much fun as that was, I was still trying to save money, which was hard to do when you were going out every night.
As the day approached I had to decide if five hundred dollars was worth an hour of sex. Was it worth it to Tom? That was something I was curious about. He certainly seemed to enjoy himself last time.
I thought about that as I got dressed. I slipped my socks on and squeezed into my panties. Then I stopped. I looked at myself in my nightstand mirror, with just my panties on and my fingers against my hips. Then I wormed my way out of the panties and went to my dresser. I pulled out my tightest pair of shorts: a purple spandex thing with silver piping. I’d stopped wearing them and was actually going to give them away soon. Since I’d been doing squats and bends, leg lifts, and running more often, my butt had gotten rounder, firmer, and the shorts molded to my body in a way that was great at parties but drew the wrong kind of attention at the gym. What the hell, I thought.
I slid them up my legs and turned around as I pulled them over my ass. If I were wearing panties I would have had very distinct lines. But I didn’t have the panties so there was just my ass and the material that hugged my inner thighs and… I faced the mirror. No, they weren’t quite riding up my middle. But if I started jogging or doing sit ups these things would go… high.
I fished around in my underwear drawer until I found it, a sports bra from when I was in high school. I don’t remember why I kept it; I’m usually pretty good about throwing that stuff away, but my bust had grown since my junior year. Not much, but just enough to make the material tight against my chest and push my boobs out. I finished the outfit with a white tank top. The black sports bra was very visible under the thin material and I looked like I’d just thrown together something and run out the door to the gym. As I spun in the mirror I saw that my cleavage was a little out of control. That’s alright, I thought to myself, my ass balanced it out.
Gathering up my gym bag and walking down the stairs I guessed I was about to bring Tom home again. I opened the table drawer and pulled out the hairbrush. I stuck it in my bag and left the house.
* * *
When I got to the gym I didn’t see Tom there, so I warmed up, did my stretches, then got on the mats and started working out on the exercise ball. I did a short, quick set of 100 crunches and then did some easy yoga stretches. Still no Tom. The gym instructors were passing by and saying hi. We both pretended they weren’t scoping out my ass and I went into my squats.
I saw Tom at the free weights. He was working his triceps, so I worked my triceps. I checked the mirrors at the far side of the gym instead of the one right in front of us. He was using the mirrors on the other side of the gym to check me out. When I set my weights back into the rack and got another pair I glanced to see if he had an erection. Either his pants were looser than they looked or he wasn’t affected. A few younger guys (I guessed they were tall for their age because they had that goofy emo thing going on) did not share his stoicism. They were gathered in a huddle on the gym floor and talking over the bench press instead of actually using it, and I could see them rearrange themselves surreptitiously. I smiled and left Tom, going to the thigh machine and sitting down to spread my legs and work out.
Tom saw that.
I finished my work out on the treadmill with a short fifteen minute run. I set the incline way up and tried to sprint the last four minutes. By the time I was finished my heart was beating and I was covered in sweat and Tom was working on the rowing machine near the door. I zipped open my bag as I headed for the door and I tossed the hairbrush on his bag. If he saw it happen he didn’t betray a single glance. I just went outside and rounded the corner of the building.
Tom showed up about five minutes later and handed me his helmet. Inside was an envelope. I opened it and looked inside: five crisp bills. I stuck the envelope in my bag and shook my hair out, pulling his helmet over me and stepping behind him after he swung up on the bike.
He knocked the kickstand out and revved the engine. I squeezed myself against him and he put his hand on my thigh. We lit out of the parking lot like we were already late for an appointment.
* * *
When we got to my place Tom told me what he wanted me to do. He didn’t want to see me get dressed, so I told him he could wait downstairs. He asked if he could have a glass of water, of all things…
I went upstairs and I showered (Tom said that was alright after I told him I didn’t want to get my clothes sweaty). I shook a little as I cleaned under my armpits and my legs, going so far as to scrub between my legs until my wet pubes snarled against my clitoris. I got out, toweled, and walked to my room, glancing down the stairs and the bannister at Tom, who sipped idly at his drink and watched me pass.
When I got into my room, I rubbed down my hair (it was pointless, I thought, since I would probably be showering soon again anyway). Then I got a silky blouse, one that showed plenty of cleavage. And since I didn’t see a reason to wear a bra, I was all but falling out of the thing. Then I pulled one of my shortest skirts off the hanger and stepped into it. I hiked it up over my hips until it was snug and then looked at myself. I looked ridiculous; hadn’t put on makeup, had just come from the shower, and if my father (or Bobby) had seen me walk out of the house with my tits hanging out like this they’d tackle me to the pavement. I brushed my hair back as much as I could and then I sat down and put on a thin layer of foundation, then did my eyelashes and finished with a bright red lipstick (that’s what he asked for).
When Tom saw me coming down the stairs it looked like he was about to whistle, then thought better of it. I padded down to him in my bare feet and he swept his hand over mine on the bannister.
“You’re beautiful,” he said.
“Mm.” My heart was thudding in my chest. I didn’t know what he wanted this time but I wasn’t prepared for it, not mentally.
He drew his fingers through my hair and slid them down my neck. His eyes drank in everything, from my face, to my shoulders, to my breasts, down to my stomach showing between the skirt and the blouse, and my legs.
“We started off fast last time,” he said. “This time…” he drifted off. He was fixated on my lips.
Without another word he took my hand and led me around to the couch. He pulled off his jacket and folded it, slinging it over the arm rest. Then he pulled off his gym shirt. I watched his pectorals flex and his stomach twist as he bent down to get his sneakers off. Then his socks (my pussy suddenly felt tickled by my pubic hair, as if the skin had suddenly come alive), then… oh.
Tom was already very hard. His long dick stuck out from his pubic hair like an angry red pike. He sat down on the couch, condom wrapper already in hand. I watched him get comfortable, then he tore the wrapper and rolled it down his dick. Before I knew it he had tightly wrapped it up in the white, lubricated latex. He crossed his legs and sat like a buddha on the couch.
“Is it alright if I’m naked on the furniture?”
I ignored him. “What do you want me to do?”
He patted his thigh and reached out his arms. I came forward tentatively, not taking his hands. I hiked up my skirt gingerly and shuffled over him on the couch. I grabbed his penis and angled it toward me when he took my wrist and gently made me let go.
“What?”
He squeezed my buttocks and brought me to a siting position on his thick thighs. My legs were splayed over him and my feet pointed up on the cushions. My head was above his and he was more or less eye level with my boobs. He smiled up at me.
“Are you comfortable?”
“Yeah, I guess.”
He reached up and touched my neck again, slid his fingers down my throat, down my clavicle, down into the impressive dip of my cleavage.
“Take them out,” he said.
All I had to do was shrug and my tits rolled forward. I hooked my fingers into the loose collar and they fell the rest of the way. He reached for them and grasped them gently.
“Put your hands over mine.”
I did. His hands were cool.