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Switch Hitting with Sally

I was sitting alone in my hotel suite in my bra and panties, waiting for my next client, watching a porn movie I’d downloaded to my laptop when I was suddenly reminded of my old friend Sally.  Only Sally and I weren’t so old back then.  This was during our last days in high school.  Sally was my best friend in the whole wide world.  She and I had come in late one weekend night from our usual foray to the family-themed park down the street. We’d go every weekend and drive the boys wild. We loved to tease them with our flirting and taunt them with our bodies.

It was all in the spirit of good, clean, teenage fun, although I suspect we were responsible for more than a couple of cases of blue-balls around the park.  We’d get back to her house, all riled up and horny as hell, and we’d kick back in her living room to calm down before I went home.  Sally’s mom, bless her heart, was usually zonked out on weed by eight-thirty at night so even though she slept in a room around the corner from the living room she didn’t much give a shit what we were up to.

On this particular evening I was lying on the couch talking on the phone with my boyfriend, listening to Nine Inch Nails and giggling with Sally when she decided to go for my undivided attention. She crept her way up my body kissing me on my stomach. I didn’t know what to do or say, so I let her continue. This was awesome! I had always wanted to do this.

Oh shit!  I still had my boyfriend on the line and I had to get rid of him before I could get it on with her.  I told him abruptly, “Uhh I have to go!” “Why?” he asked. I didn’t want to interrupt Sally’s insistent distractions to explain it to him although I’m sure he would’ve loved to eavesdrop so I just hung up.

Then Sally dove into my lips. We were going at it on her couch in her living room and her mom was right around the corner in her room asleep. This was going through my mind as we tumbled to the floor hastily trying to undo each other’s pants and get our panties off.  Her mom was notorious for getting up in the middle of the night for a midnight snack.  Pot does that to a person.  Or so I’ve heard.

I got Sally on her back, lifted her shirt and took her bra off.  She had the most beautiful breasts and nipples; size 36C with big, dark brown areolas. I gobbled every bit of them in my mouth. Of course Sally returned the favor. Then her hand slipped between my legs and she fingered my tight wet teenage pussy. I did the same to her.  Sally had a full bush and mine was shaved.  I asked her if we could shower together and her pretty face lit up with a happy grin. We ran naked down the hall and jumped in the shower, playing with our wet bodies, pressing them against one another, taking turns rubbing our pussies on each other’s legs, kissing and grabbing, and of course licking. Sally even let me shave her pussy.  I shaved it bald and then went to town on it with my tongue.

We got out of the shower smelling good enough to eat. We went to her bedroom where she put on a porno. We watched this raunchy video while going down on each other. Her pussy tasted so sweet when she came. I didn’t know what to expect at the beginning of the experience, but I found out I really liked the flavor of that forbidden fruit, and I’m sure Sally did too.

After that Sally and I continued to fuck each other silly whenever we’d spend the night at her house. One time we even included a couple of boyfriends in our frolic. But I have to save that for another story. I hear a rap upon the door and I sense my bra and panties will soon be on the floor.  Ciao!

Geezers Need Love Too

I need to warn you upfront, if you’re the type of reader who’s only looking for a lot of fast and furious sex in these gentle memoirs, you’d best skip right on past this one.  If, on the other hand, you’d like to meet my favorite trio of geriatric gents, please read on.

Bud, Roy and Charlie come to visit once a month, the day their Social Security checks hit the bank.  Thank God they don’t all get paid the same day of the month.  Otherwise I’d never get anything done.  Now I’ve never imagined myself doing pro bono cases, or even caring for shut-ins.  Don’t get me wrong.  This isn’t charity work - even though I offer all three the courtesy of an AARP discount.  But frankly, had you suggested to me at the outset of my dubious career that I’d end up servicing the prurient predilections of a nefarious network of senior citizens, I’d say you were off your rocker.

Perhaps part of my quandary is that my own Dad departed this vale of tears when I was sixteen.  The rumor was he might have ended up in Boise or Reno but those tales were largely unconfirmed.  All I know for sure is he skipped town for greener pastures.  So maybe my caring for Bud, Roy and Charlie stems from some sort of an Electra complex but I don’t think it’s all that cut and dried.  Aside from their physical infirmities (and I do mean as in Not Very Firm!), they are three of my least demanding clients.

Last month on the eleventh, right on schedule, Bud called me up and reserved his regular hour for 4:00 in the afternoon.  All three of my boys like to book a mid-afternoon session so they don’t miss the Early Bird prices at the buffet downtown.  Bud spent his working years as a middle manager for a defense contractor in Orange County.  He has a Master’s degree in Public Administration and has done some work on his doctorate.  He isn’t dumb by any stretch of the imagination.  How do I know so much about his personal history?  Bud has entertained me with his life story at least a dozen times.

Bud likes me to undress him slowly.  Then I make googly-eyes at his limp dick and say, “Ooh, I’ve never seen one that big before, I bet you made the girls real happy back in the day!”  I push him down on the bed and do my level best to get a rise out of him but it seldom works.  He is, however, happy with my effort to arouse him.  Once we’ve determined he isn’t gonna pop (again!) we lie there together on the bed and he tells me detailed stories of his reckless youth and respectable middle age, how his wife of thirty years passed away from the cancer the same week Bud retired.  He isn’t bitter or pessimistic about any of these events.  But, Oh My God, does he love to rattle on.

One of the delicate problems I face with Bud, Roy and Charlie is that they use up the whole fucking hour.  When it comes to my young Studs, they get off, get up and get out.  With these three I have to keep an eye on the clock because if I don’t interrupt them in mid-reminiscence, dress them back up and get them out the door, they’d easily run on for hours and probably miss the Early Bird special in the bargain.  Still, by God, I love my over-the-hill boys to death.

I’m gonna climb up on my soapbox and rant a little.  Some folks believe sex work is a crime against society; that the money I earn from my labors should be used to feed the hungry mouths of the children legitimately sired by my clients.  Yet, who among you suffers when I make life a bit more pleasant for Bud, Roy and Charlie?  And is it a sin for them to indulge in an hour of harmless play just because sex is involved?  It doesn’t hurt a single soul.  Besides, it makes me feel really special!

Role Play and Pole Position

I suppose you might call me a frustrated thespian, because I love to role play. That’s Thespian, not Lesbian, although I freely admit there have been times I’ve indulged my Sapphic nature as well. In fact I believe the concept of Role Play fits the androgynous model like a hand in a glove but today’s topic of discussion is role play with a member of the opposite gender so try to focus.

Scheduled role play sessions are extra fun for me. After all, in most of my regular sessions I pretend to be the client’s girlfriend anyhow. Most times a client wants me to play the part of a young coed while he plays the part of an older Sugar Daddy. This interaction doesn’t necessarily require a costume. Oh sure, sometimes the guy wants me to put my hair up in pigtails and wear a white, cotton blouse and a plaid skirt, maybe a pink ribbon in my hair and bobby socks, but he really doesn’t have to dress up at all. The stock costume for a pretend Sugar Daddy is the same as street clothes for a normal guy. The main difference is, when a dude pretends to be my Sugar Daddy, he doesn’t have to pony up the rent every month.

Tony’s request was different. He called and asked if it would be okay for me to play the role of a mistress who had been caught cheating on him. He gave me a laundry list of clothes to wear. He also asked me to have some pictures in my purse showing me and another guy banging away on a ratty bed in a sleazy hotel room with the shades down. What the fuck! I can say it wasn’t much of a stretch for me to get into the role and God knows I had plenty of raunchy pictures but I couldn’t for the life of me figure out what Tony’s game was. He was a favorite client of mine and he’d always been pretty meat and potatoes when it came to doing the bad nasty. In fact I can’t recall any position with Tony besides missionary, even though I’d hinted broadly that other options were on the table.

I dressed up in the light blue, cashmere sweater and tight jeans (no panties!) Tony asked me to wear and sat on the edge of the bed to await my deceived lover. As an aside Tony is an attorney in a prestigious law firm downtown and it wouldn’t do his reputation much good to have his secrets spread around. Listen, his secrets are safe with me. My lips are sealed.

Right on time, Tony knocked on the door and stormed into the room, demanding to see inside my purse. I reluctantly took out the pictures and showed them to Tony. He was livid. He grabbed me by the ass, unbuckled my belt and tugged off my tight jeans. Then he ripped off my sweater and bra. I cowered naked at the edge of the bed while Tony threw off his own clothes. I was amazed to see how stiff his cock was! He turned me over the bed and began to spank my ass. The torn clothes were part of our deal but the ass-spanking was starting to hurt. Still, there was a subtle thrill that went with the pain and I was starting to get into the submissive role pretty good.

Tony ran his fingers between my ass checks and over my tight little butt hole. My exposed pussy was clinching hard and I could feel my wetness growing. He stroked it with his finger, circling, rubbing it, and spanking me hard with his other hand. I turned my face up to Tony and suddenly his cock was in my mouth. He rammed a finger up my ass and I heard the angels sing. Holy fuck! I was coming and gagging and he was coming and roaring and then we both collapsed in a heap of laughter and tears.

Tony still drops by from time to time but we’ve never tried to repeat that particular scenario. Sometimes a play works best when you don’t know how it’s gonna end. Ciao!