I did something recently I haven’t done in years, I did a bit of escorting again for money. I had been doing ok, but recently had some large bills come up I simply could not cover, so I called some old clients up and let them know I was available once more if they wanted to see me. Several were thrilled to be able to book an appointment with me once more. It honestly felt like no time had passed, it had been a few years, but it was pretty easy to go back into that mindset. I made what I needed within a couple of weeks of bookings.
The one client in particular was glad to hear from me and I was glad to hear back from him when I’d left him a message. He had always been my favorite client, I would have fucked him for free he was so hot. He was terrific in bed and always made me really cum. I loved sucking his hard shaft and riding his cock up and down, no one ever made me feel like he did that wasn’t a real boyfriend, it was truly a pleasure doing business with him.
He saw me a few times during those couple of weeks and I looked forward to each and every time we met. I may continue to see him and him alone even though I won’t need the money, but I can let him think that I do, so I’ll be getting to fuck him and getting the bonus of getting paid as well. It’s always nice when you really enjoy your clients, most you don’t, most are tolerable, but the rare one is a treat you enjoy as much as they enjoy you. If only they were all like that.
A caller the other day brought up a celebrity that’s never come up in a conversation before, Donna Reed. He wanted me to describe in perfect detail how I’d dress him up as the perfect 1950’s housewife. Now I hadn’t seen that show, but saw just about every episode of Leave It To Beaver, with another perfect 1950’s housewife, June Cleaver, so I assumed the look was pretty much the same, perfect hair, wearing pearls and pumps to vacuum the house, always looking perfect after housekeeping all day and cooking for a family.
He was quite detailed, abut the full skirts and how to get the skirts looking full like that, there must be a crinoline under them, it would be the only way possible to have that full look. Full slips, a girdle, stockings, hairspray in the hair to have it keep its shape, he had it all down pat how he wanted me to dress him up. He was of course to be dolled up like this to be very attractive to the men I was going to bring in to fuck him. He wanted to be the ultimate feminine woman, so feminization was his kink.
I’m not sure that many men are fantasizing in today’s world about a woman groomed like that, but some are no doubt, everyone has their fans I’ve learned, no matter how obscure. He wanted his hair perfectly set, his makeup perfect, and his stockings and lingerie all just right, then the crinoline and full skirt, he’d look so pretty as the men came in to fuck his mouth and take his virgin ass. We all have our role models or celebrities we find very handsome or pretty, many times we want to be made up to look like them, celebrities can add to your sexual fantasy bank for sure.
One regular caller is obsessed with his pocket pussy masturbation toy. He tells me how he can’t get girls, what a loser he is and how he masturbates several times a day with his sex toy, his pocket pussy. He sounds like a loser, just from his voice, I can only imagine what he looks like. I do not find it hard to believe that any woman would reject him, he’s got zero confidence and just sounds so pathetic. I cannot even imagine a hooker accepting him. So a sex toy will have to do!
Some callers do use Fleshlights, pocket pussies, prostate massagers on calls, that’s quite common. One said the pocket pussy feels so good, it’s hard to not cum as soon as you slide your dick into it. Sex toys are really so common now, it’s hard to think only the last few decades have they been as widely available as they are now. People had to make do with homemade contraptions or use things not designed for that purpose, it’s wonderful that there is now the variety for people to enhance their sex lives. Not everyone uses toys of course, but for ones that do, they have everything from the most basic of toys to ones you can use remotely on others, all kinds of options are available.
He uses it daily, usually several times, and he said he’s afraid the cleaning lady saw it, since he hadn’t put it away as fully as he should have, and what must she think of him. I said she thinks you’re a loser that can’t get women, which is true, and that the toy is your girlfriend. He agreed that this is probably what she thinks of him now, lol. I’m sure she’s seen lots of secret things at people’s homes, but he thinks of this every time he speaks to her now. He should just come out and ask her if she saw his pocket pussy and what does she think of him. That conversation I’d love to be a fly on the wall for!
I was a naughty neighbor recently, this young guy moved in next door, and my bedroom looked right across at his, and I walked in the room one night with my light out and I could see him jerking off as he was watching porn. Of course I had to watch, it was fun, I know I shouldn’t have, but he had a really nice dick. Several times a month I’d see him do this and began to think he was doing it like this since he knew he was being watched, or he’d have drawn his shades down and he had not, not even one time.
So I did the same thing a few times right after I got out of the shower, I had my light on and dried myself off and then laid down on the bed and masturbated. I don’t know if he saw me or not, but it was fun thinking he might have been watching me. I turned my light on and his was off, maybe he wasn’t even there, I don’t know, but the idea of being watched as I pleasure myself really turns me on.
I must be a voyeur and an exhibitionist, since I enjoy both equally. Maybe one night we will both be doing it and looking over at each other at the same time. That’s what I think about as I’m rubbing my pussy and glancing over at the window anyway, wondering if he’s watching me stroking his cock in the dark as I do. Maybe he has binoculars or a telescope and is watching it up close, I’ve no idea, but I do enjoy it.
When I was in high school there was this one teacher I really wanted to fuck, I was determined I was going to have him, and I did end up fucking him eventually. He was a single father and he needed babysitters sometimes and he would ask various girls in the class to do it and one time he asked me and when he came back home both of the kids were asleep in bed and I could tell he’d had a few drinks, and I knew this was my chance to get him, he was more vulnerable and liable to give into his desires.
I checked on the kids one last time and when I was on my way out of their room I saw he was already in his room down the hall, so I went in and I closed the door behind me. He was already half undressed on the bed and I started to rub his shoulders and soon we were tumbling in the bed together and he had a rock hard erection, and I knew it was just aching to get into my teenaged pussy. I didn’t make him wait long. I was undressed in a moment and laying on the bed spread open for him, and when he slid that cock inside of me, I gasped with pleasure.
He fucked me better than any boyfriend ever had and I came several times on his cock. He knew just how to please a woman. His cock was long and thick and spread me open nicely, and I loved how he thrust and moved inside of me, it was insanely intense and I bit my lip to keep from crying out. We had fun several times after I’d babysat for him, and I have fond memories of our times together.