Ruby’s New Life Part 5

When Grandpa and I arrived home after my shift at the tavern, Grandpa removed my anal plug and I showered to wash off the oil before bed. The slick soap on my new nipples and clit were tough to handle. I managed to hold off making myself come, Grandpa reading on the toilet helped. I didn’t want to know what punishments were like.

When he hooked me to the machine in bed, he put it on a low setting. “Nothing too fast to start with. I don’t want to send you over the edge.” He turned the TV on to a porn channel and I fell asleep watching a group of men soak a woman with their semen.

In the morning, Grandpa stopped the machine and released my restraints, “You need to hydrate, Ruby. You’re so much wetter than you were before all of our conditioning and alterations.”

“Yes, Sir.” He handed me a glass of water that tasted like lemon and I gulped it down.

“Breakfast is ready, brush your teeth and meet me downstairs.”

“Yes, Sir.” I used the bathroom and brushed my teeth, then went downstairs and lowered myself on what looked like a new dildo on my chair for breakfast. It pushed further into me than my other one did and I had to relax to take the length of it.

“New seat for you!” Grandpa smiled, “It’s a cast model of Kyle’s penis. He wants you broke in properly.”

‘Broke in’ … like I was a shoe? I didn’t say anything, just enjoyed being filled and imagining Kyle’s handsome face while I ate.

“Kyle will be coming by just before lunch to take you shopping in the city. He seems anxious to spend more time with you after last night. He doesn’t have much time before school starts.”

“School is six months? So I’ll be done in the spring?”

“Yes. It’s a boarding school, so you’ll only be home on holidays.”

“I’m getting kind of excited for it.” I had to admit, finding out what this was all about was making me curious.

“Kyle will be here before you know it, we better get your exercise and pool time in. Go get your running gear.” He told me he would do the dishes and I went upstairs.

I noticed it was the white ‘sports bra’ and mesh shorts. I was thankful it wasn’t the dildo shorts this time, I didn’t think I would be able to handle that right now. Though fantasizing about that seam rubbing my new, swollen and exposed clit made me want it a little. Maybe it would be worth the punishment to come just once?

When I was dressed, we left for the track. Riding in the car on the dildo didn’t help things. I was hornier now than I’d ever been when I was having sex regularly.

Running was more difficult now as well. Once I was drenched with water, my nipples felt like they were pushing out with desperation and I was getting wet. With every step, the slight vibration felt like it jostled my clit. Not enough to please me, of course. My mind was constantly aware of my arousal. It did help take my mind off my running and I made three miles before I even realized it.

On the car ride home, I kept hoping for huge bumps or potholes so I could bounce on the dildo. I noticed a stack of papers in a file on the dash and asked Grandpa about them.

“Those are my own prospects. It’s getting to be time for me to select a new partner.”

“A new wife!?”

“Yes. My mourning period has gone on far longer than most and I’m being pressured. Also, Ginger’s husband has been loaning her to me for my needs and … I think he’d like her back with him full time.”

“So who are these women?”

“Eh, widows, women from the outside curious about the lifestyle…they’re usually pretty risky; they change their mind about the lifestyle more frequently and leave. There are some younger girls too … but that just doesn’t seem right to me.”

“When do you have to choose?”

“I’ll make my choice today while you’re on your date with Kyle.”

I desperately wanted to thumb through those pages, but I stared out the window and minded my own business.

I soaked up some sun by the pool and came in to shower and get ready for Kyle to pick me up. Grandpa monitored me in the shower, gave me a quick anal douche and put in a plug for me so I could finish my hair and makeup.

When I was ready, I went into my room to find the clothes Grandpa had laid out for me. There was a black flowing skirt longer than most that I owned, but that only came to mid-thigh and a red, silk spaghetti strap tank.

“No bra. The red color will hide the color of your nipples, but the fabric will let them show themselves enough to please Kyle.”

When I put the clothes on and looked in the mirror, I wouldn’t have looked twice at me unless I was focusing on my nipples. The thin fabric grazed them and made them stand at attention. The sensation was incredibly sexy.

I put on black mules with a heel and no sooner had I slipped them on, the doorbell rang.

When I went downstairs, I found Kyle and Grandpa talking.

“Ah, Ruby. You remember your fiancé from last night, yes?”

“Yes, Sir.” I could feel myself blush a bit as I looked at Kyle and he made full eye contact with me.

“Ready for some shopping, Ruby?” His voice was like smooth caramel.

“Yes, Sir.” I smiled and we left to get in his car.

He was driving a sporty Cadillac sedan and when he opened my door for me, I saw a dildo much like the new one on my chair in the kitchen. I slowly lowered myself onto it and moaned as it filled me.

When Kyle was on the road finally, he started small talk. He wanted to know where I grew up, what my family was like, even school and how I had done in my classes.

“I’m pretty progressive. When we’re married, if you’d like to go to school and further your education, I won’t object. I love intelligent women.”

“Thank You, Sir.” He wasn’t such a caveman after all!

“I just wanted to spend today getting to know one another and let you know what my expectations are in a wife. Obviously you know a lot from my profile. My family has money, but we don’t flaunt it or act like spoiled assholes. I had to work my way through college even though my tuition was covered by my parents. I’ll be starting with a firm in the city in the fall, about the same time you go to boarding school.” He smiled and sped up to merge with traffic on the freeway.