My Tuches (anal) virginity. From Foy to Oy, to Ahhhh.

   

    I would sneak into his office from time to time because I always made sure to forget something on his desk. A piece of paper, my favorite pen that had my name inscribed in Hebrew which I got from my mom as a Chanukah gift. I’d always find a way to enter his territory to use that particular coffee machine. I left like it produced better quality coffee than the one in the main employees office. Since my sex drive is always through the roof, and my lips are always engorged, yes, both sets; I can’t help but dress a bit borderline untznius (immodest) to attract his attention. For example, I would wear trendier shoes, fitted tops where you don’t have to work too hard to guess my cup size, and dab on lipgloss to flaunt my pouty lips. I also wore a tad more makeup and looked my boss in the eye with lust. He totally knows. I drive him crazy, but he reciprocates. We both feel an immense sexual attraction toward each other. My heart loves this game. My mind too. Lots of dopamine and other feel good hormones flourish through my body every day at the office. Sometimes I bring along an extra set of Panties double bagged, hidden in a secret pocket in my bag. I get so lubricated just from thinking about all the naughty stuff I want to do with him. All The stuff I have done in the past. I love the idea that everyone else thinks that I’m a very holy, chusheva (well respected)** woman in the community because i’m the wife of this big tzadik, my husband. Except for my boss, the electrician, my dentist, and everyone  that used their tools to play with my mind, body and soul. They know….

Kink? I always thought there was one definition of that word; curly, twisted. Kinky peyos or side locks. My boss is the one to blame for enlightening me and opening up my mind to a whole world of twists, sticky peyos, cummy shpitzel (headscarf) assplay, spanking, light BDSM and more fetishes.

    My boss, my very sexy boss. I can still see the little dry scab  on his forearm from my nails. Glad it’s healing quickly and drying out, unlike me.

I never get dried out.  I dug into his skin deeper than his cock penetrates my throat. Love the confidence and sex appeal that oozes through his tall, straight posture. I smiled, looked down at my desk and got a tingle directly onto my clit every time he walked past me and his flying tzitzis (fringes)would hit my lower back. That reminded me of the fun “meeting” we had in his office one afternoon. He is clearly a butt-man. The real word is TUCHES. Such a nasty, dirty, perverted word. See, in the english language, ass has too many slang words like: booty, backside, behind, buns, butt, cheeks, to name a few. In yiddish, the word “tuches” awakens a dirtiness in the brain like no other. 

    I got very close to my boss since our first tight, long hug. We spoke a lot since then. He too opened up to me about his personal life, how he’s struggling at home, and his wife won't respect him. He was and still is a deprived man too, sexually. 

It was probably the time I ovulated, a few days after I dipped in the mikvah, I was heavily aroused and couldn’t contain myself. I felt like the biggest slut. I got naked in front of the mirror in my bedroom and admired my smooth, sexy young body. My flawless skin, enormous but perky breasts, looked very inviting. I almost wanted to kiss my own reflection. I shave everywhere except for my head (although I pretend I do. shhh). As I was getting ready to grab some snacks to put into my work bag, I noticed a pink post-it note sticking out from a side pocket. It read in Yiddish, no need to wear panties to work today with a little smirk face drawn at the end. A rush of blood took over my head and made it feel heavy. This is way too risky! What if someone sees that note? I was angry, but exhilarated. I was already dressed to go into work. I froze, ran into the bathroom and kicked off my shoes, pulled down my thick, beige, palm tights and panties and threw it into the hamper. Pulled up the tights, slipped back on my shoes and ran out the door. Every step I made without any underwear felt so sinful. It felt so wrong. Everyone who looked at me, felt like they knew about it. My mind was racing faster than my heartbeat. I couldn’t stop thinking about what he is going to do to me today. I knew it was a busy day packed with meetings, lunches with clients, and phone conferences. I guess his dick kept a different calendar. Office work had my mind engaged for the first two hours of the day. Under the desk, I was jerking my foot in and out of my shoe from nervousness and extreme eagerness. The crotch on my tights started to feel damp. It was the rough fabric that was starting to irritate and slightly stimulate my private bits. He’s here! I stared at my computer screen frozen. I knew that if i turn around to face him I wouldn’t be able to resist my smile, and the other co-workers would notice something fishy. I had to grind my teeth and bite my lip. The sexual tension was so thick and heavy. He called into my extension, and I picked up. “I want your tuches oifen tish now” (ass on the table). My face probably turned purple. My heart was about to jump out of my chest. He never really talked about ass in general. I locked my computer. Backed out my office chair and got up. I knocked on his door twice and slowly opened the door and shut it behind me. “Lock it” He shouted. I did. I thought he was a bit rude and weird but I didn’t think too much of it. 

    He asked If I ever heard of BDSM. I said I have read about it and would have loved to have the opportunity to try it. He said in a bossy, demanding voice, “I’m the Dom, and you are my sub, now get on your knees”. He didn’t ask, he told. I found it so hot and manly. I felt like I was in my place where I needed to be. I wanted to worship him. It felt very natural to be on all fours directly facing him. I didn’t budge. My hands and knees were in direct contact with the cold floor. My ass was up in the air. My head was tilted up to see what he’s about to do next. I was still all clothed. I heard the shuffling of his buckle bet. He removed it and folded it. He whipped it in the air to create a loud whip crack. I shuttered. He warned me not to move. He was also very reassuring that I’m safe in his hands, to trust him, and he won’t hurt me in any way. I did feel safe. He removed his oversized chassidishe pants and his long, white underwear. All of a sudden, naturally, my tongue fell out. I had this hunger and crave for his pulsating cock. I wanted his warm, veiny cock in my mouth so bad. I felt like a dog, acted like a dog and was in position of one. He walked toward me and I immediately latched onto his cock like a hungry bitch. I was salivating. I stuck my tongue out the longest I could and with the tip of my tongue I started licking the base of his shaft. I licked it very slowly but eagerly. From base to tip. He let out a groan and his head flew back. His yarmulka fell on the floor but Noone seemed to be bothered. I loved watching his dick grow even longer with every licking stroke. I painted his entire cock with my tongue. I loved worshipping it. I took his ball sack and licked around it. I played with the tip of his dick, where he had his bris cut off and teased that sensitive spot. It was so veiny, thick and ready to explode. I had my lips tightly around his eiver (cock) and started sucking. It made my pussy soaked. He pulled away from me. He didn't want it to end so quickly. He walked behind me and asked me to stay put with a stern voice. He lifted my skirt up and stared at my ass. “Good girl, you listened,” he murmured. I closed my eyes and my face was flushed. I must admit, I have a cute, tight ass. He was dying to spread it. I know he was. He shlepped off my tights and spread my ass cheeks wide open. “What  a beautiful pucker you got there” he said. I was so embarrassed. Ass was always so wrong and taboo. It is the dirtiest place on the human body. I guess that is what makes it so enticing. I would much rather go to the OBGYN 35 times a year and have scary tools up my vagina than have my boss stare into my asshole, my most intimate spot. A place where my husband never even looked at or touched, let alone spread and stare?! His face got closer and closer to it. I wanted to die inside. Before I had a chance to feel emotions, I felt a sleek wetness almost like a slug crawling around. I could feel my boss’ beard and his warm breath directly on my asshole. He was eating my ass out like it’s his last day on earth. I felt so anxious and embarrassed. I hoped it was clean and not too sweaty for him. I wasn’t prepared for this. My mind was wondering. He then started massaging the hole. He dipped his pinky into lube and drew circle motions on the pucker. He massaged it. It felt amazingly pleasurable. I wanted him to stick his pinky inside. I begged him. He finally moved his pinky in. I pursed my lips and squinted my eyes from the delicious pain and pleasure. I wanted more. I wanted something bigger and harder. He sat up on his knees and handed me his yarmelka and said, “if you need to scream, cover your mouth with this black, velvet yarmulke so no one could hear you”. I listened like his obedient little slave. He smeared lots of lube on my asshole and placed the tip of his cock onto it. And started to push it very gently and carefully. 

    All this made me exceptionally horny. My pussy was very jealous of its next door neighbor, the ass. But she still wanted a good pounding. She was hungry, very, very hungry. As my boss was breaking through the dirty walls of my Assidish yiddisha tuchus, he also fingered my sensitive, pink clit to tame it. He pushed harder and forced his humongous cock into my ass. I grabbed the yarmulka, sealed my mouth with it and let out a deep, whimper. It hurt like hell. But a pain that quickly turned so pleasurable. I wanted my pussy filled at the same time. He came seconds later, and sprayed my back with warm, milky cum.