We are both in our early 50's and live out West. I've had a crush on her but I'm sure my wife wouldn't approve. She is attached as well so other than dream of this I've never acted in a way that would be bad for business. She smelled great and I let my hands find her waist through her thin dress. Her hands had my cock free and she nibbled at my neck driving me crazy."I've thought about this for some time," she whispered, "You're just what I want, right here and now."With that she pulled me around by my dick to face her and our mouths met with deep kisses and our tongues searched each others. Her hands stroked me in a controlled deep fashion, just enough to keep my hard. My hands roamed and discovered nothing but a sun dress kept her from me.She pushed me to sit on a hay bale nearby and straddled me."Ouch, I thought hay was supposed to be soft!" she said as her tender calves met the alfalfa stems, scratching them slightly.She stopped for only a second to hike her dress up and impale. My cock throbbed with excitement. I heard Mistress Sarah say, "I'm going to enjoy fucking your tight little sissy pussy." Then I felt her strap-on push into my arse. Wearing the plug all day, kept my arse stretched so that her initial entry was not too startling. However, as she pushed in deeper it stretched my insides and I tensed and moaned. My moan was muffled by the dildo still in my mouth. "Relax, bitch," instructed Mistress. "Take it like a good sissy." Mistress Sarah rested for a moment with her strap-on about 1/3 the way into her sissy's boy pussy, allowing me a moment to get used to the fullness. Then she pulled back and then pushed in again going deeper than the last time. I continued to moan in discomfort. Mistress Sarah coached me with a firm commanding tone, "Focus, Evie....relax and take my cock in. Come on slut; show me what you’ve got." Mistress did not ease up. I had no choice but to open up to her and accept her. Her rhythm picked up just as I was getting used.
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