The first time I tried anal sex was with my wife, but even with lots of lubricant I couldn't get more than two inches of finger or just the knob of my penis into her asshole before she cried out and made me stop. She made it clear that if I continued with this sort of experiment I wouldn't be putting my cock into ANY of her holes!
Some months later I had a work project that needed me to stay overnight in the City once a week. The job paid a fixed daily amount for expenses so I chose a cheap, but clean hotel in a bad part of town and that meant I had money for other things.
Two teenage girls seemed to hang around a lot outside the hotel and asked passersby, "Do you have any spare change?" I'd give them a few coins and chat with them. At other times they would ask, "Can you spare a dollar for bus fare?" though I never saw them at the bus stop!
One day I bought them a meal of burger and fries that they ate hungrily. "If you were old enough you could come up to my room and earn some real money." I offered. Amy, the older girl, said they were old enough for anything I wanted to do, but I had my doubts about Betty. However, when I told her that, Betty produced a grubby Wisconsin driver's license showing she was eighteen years and three months old.
Reassured, I took both girls up to my room in the hotel. It was the sort of place where all types of people were coming in and out, so nobody took any notice of us.
"You can do anything you like, but no anal sex." Amy said. She was slim and dark and stripped quickly after I gave her a few dollars. Betty was hesitant, but took off blouse and bra then dropped her shorts and panties. She was pale-skinned with almost no pubic hair, while Amy had a thick brown bush.
As we'd agreed, for the first time I fingered their bodies and sucked nipples while they took turns licking my balls and sucking my cock. As I got close to cumming, I knelt above Betty and Amy stroked my penis until sperm shot onto Betty's breasts. That was very nice!
When I saw the girls the next week Amy was ready for me. "You need to get your cock into us," she said, and I did. I lay on my back while Amy first sucked me, and then squatted to take my penis into her vagina. I pulled on her nipples, and reached over to explore Betty's crotch until I came.
In those days I could recover quite quickly, and by the time we'd eaten some food I was ready to push into Betty. I'm sure she'd been fucked quite a lot, but there was an innocence and tenderness about the way she tried to encourage my thrusts. Amy fingered my ass and balls and I exploded into Betty's tight vagina.
Amy kept asking for more money and offering more ideas. One time she lay in the bath tub and I peed over her lower body. This golden shower was not something I felt the need to do often, but I did find the experience very erotic.
I rinsed her and cleaned her crotch with soapy hands and a slippery finger felt for the back hole. "I'd pay more money to get up your anus," I told her, but she said she couldn't. "Then why not get Betty to open up for me?" I asked.
Amy's eyes opened wide at the thought of selling Betty's virgin ass-hole. "I know she's never done it, but I don't know who she's saving it for, if not you." She went into the bedroom and I heard Betty gasp and then she started crying quietly.
