I met Sandra the first time on a whim when I spotted her massage add in paper. The massage therapists in town with quite wild and erotic and I didn't have nothing to lose sexually straightforward forward questions. I called her up and asked her if she could fuck my ass with a strap on? Not saying no she immediately questioned me whether I was from law-enforcement? After listening to my story about being divorced from my ex-wife who used to screw my ass she started getting ready to say yes. Finally sensing that I was legit she invited me over reminding me to bring my own harness and dildo giggling that she had plenty of lube. I was quite excited about meeting this lady who was willing to pleasure my ass with a good screwing that I was deprived of from my ex.
She lived about 10 miles away so I took off in my car to her downtown flat. Knocking on the door I was met by this cute middle age 5'8" tall, 105 pound naked lady, with dreads, 34B breasts, with no shame on her face, inviting me into the house. Liking what she saw she immediately told me to get naked. I had brought her my own harness and dildo as demanded so while I stripped she strapped on the dildo. Sandra had told me over the phone she was definitely experienced with a strap on and had actually fucked several lesbian girlfriends before with one. She had an antique rocking chair and told me to face the back kneeling on the seat enabling her to stand and fuck my ass. This was a perfect way to trap me to the back of the chair so I wouldn't try any funny business while she fucked my ass.
After snapping on a rubber glove greasing the dildo and my anus Sandra looking like a real Dyke was excited about fucking my ass. I brought a smaller 6 inch dildo because I didn't know how skilled she was but truthfully before I knew it she found my anus and started screwing me like a pro. In less than five minutes behind her closed locked door I was getting it in the ass. Having been fucked by several other ladies I knew Sandra was definitely experienced and giving it to me good. Something different was going on, she wasn't fucking me for my pleasure but fucking me for her own pleasure. She didn't allow me to touch my cock and told me to concentrate on the dildo going in and out of my ass. I didn't even get an erection because the feelings of the head of the dildo sliding back-and-forth against my prostate was so thrilling. At the same time Sandra was carefully pushing the base of the dildo against her clitoris to turn herself on. My prostate was definitely getting a work out but Sandra really wanted the pleasure all to herself. The pace became frantic and her breathing was out of control as Sandra orgasmed finally stopping pulling the dildo out of my dilated ass.
Both of us were a little ashamed but definitely wanted to do it again. Ordering me to get dressed my time was up, Sandra made me promise to call her when I got home. Once I got home I couldn't wait to call Sandra. She answered the phone immediately and we talked for a long time about what we just did. When she found out that I was single and looking for a mistress she told me she could definitely fit me in and make me her house boy. A few days later Sandra took me on as her apprentice slave testing me doing chores, driving her places, cooking meals, paying bills, and being her escort at the nude beach.
Ruling her household with the lash I found out that Sandra was a fearsome mistress when it came to discipline. Being her slave there was never a massage, butt fucking, or whipping without payment. Not wanting to get taken advantage of Sandra felt it was quite appropriate for an after work slave to pay for both pleasure and discipline. We definitely enjoyed each other's company as Sandra taught me my place under her so we both got along fine. We enjoyed each other's company and could make each other laugh which we both needed. Everyone at the nude beach knew that I was Sandra's slave and never inquired about my tell tale marks from a recent whipping. All of the women at the beach were female dominants and were actually proud of Sandra for making sure I was obedient by using the lash.
At the beach Sandra loved to show off her power in front of her girlfriends embarrassing me by explicitly talking to them about her exploits, either fucking my ass or giving me a whipping. One afternoon Sandra and I took a dip in the ocean and after getting quite sexually playful I ended up fucking her in waist deep water. Everyone on the beach knew what we were doing and began wondering what Sandra's response would be. I was standing as Sandra was riding my cock with her legs wrapped around my waist as we French kissed. Her vaginal muscles were squeezing and kneading my cock so I didn't even have to move until I finally came deep inside her. Sandra sensing when I came, broke the kiss and whispered in my ear that I would have a price to pay fucking in front of her friends.
Slipping off my cock she stood before me and started cursing slapping my face hard promising me a whipping. Sandra was forced to show her dominant girlfriends that she was still in charge. Everyone curiously watched Sandra wondering what she was going to do next. Grabbing me by the balls quite embarrassingly, she led me down the beach to a private rock where there was a stand of fresh growing cane blowing in the breeze. Ordering me to cut a fresh 4 ft. cane and make it ready for a whipping, I quickly obeyed.
Standing by my side Sandra pushed two fingers into her just fucked pussy retrieving enough semen coating both of them. Ordering me to open my mouth she stuffed her fingers with all the come into my mouth forcing me to lick it off. At the same time she thanked me for the great fuck but was going to have to whip me to save face with her girlfriends. Taking the cane from my hand Sandra actually apologized but told me to take it like a good slave to honor her wishes. Forcing me to stand and lean against the rock with my hands up she stood behind me and started whipping me from my shoulders all the way down to my calves lightly at first rhythmically snapping the cane against my bare wet flesh to gain my false confidence. Slowly she increased the intensity until I was crying out after every blow and my body was writhing with each strike. Finally, when Sandra was satisfied with my body streaked with welts she handed me back the cane grabbed me by my semi-erect cock and escorted be back to our blanket.
I was still in tears, my bare whipped flesh stinging as we drew near to our beach blanket embarrassing me with everyone watching. They all knew exactly what Sandra was up to but never said a word gawking at my well whipped body. With a big smirk on her face Sandra made me lay on my belly on the blanket straddled my body then began massaging a healing ointment into my welts. Wearing welts showing them off was a must being Sandra's slave. Lewdly she began rubbing her own body with the ointment placed herself over my body using it as a way to massage my welts with her entire body. Usually it would be an erotic stimulation but her body rubbing against the welts made them sting all over again. Simulating anal intercourse she began rubbing her pubic bone against my tailbone getting herself quite turned on. Some of her girlfriends began openly masturbating knowing what Sandra was going to do to me once we got home. "Frottage" was frowned upon on the beach but today nobody complained. Sandra was so turned on stimulating her clitoris against my tailbone she actually cried out openly coming in front of everyone.
Things got even more out of control after that when she started squirting juices all over me and then stood up and started pissing giving me a golden shower. We quickly gathered up all of our things as Sandra nastily pushed her middle finger up my butt escorting both of us back to the car. I carried the souvenir cane with a promise from Sandra she would use it until it broke. Kiddingly Sandra told me that her girlfriends were never going to forget the show today. My body was still hurting from the intense caning but Sandra was so exciting she promised to use this method of discipline more often.
I drove us home and we took a quick shower as Sandra played with my asshole finding it clear enough to fuck. Not wanting to hurt me she strapped on her best tightest harness and a seven inch dildo where the base would fit snuggly against her clitoris so she could enjoy fucking me. Taking me to bed flopping me flat on my belly Sandra quickly impaled me on the dildo using my ass to stimulate her clit to several orgasms. Depriving me of any prostate stimulation she kept the dildo completely buried inside my ass grinding away giving herself all the pleasure. I also had a huge erection pressed into my belly with no way to stimulate myself other than squirming against the sheets. I was prohibited by Sandra to have an orgasm so I could only get close. Finally she pulled the dildo out of my ass giggly telling me that this was exactly what her girlfriends fantasized about her doing to me at home at the beach. Sandra sent me home to deal with her clients telling me she would call me later.