It had been a few years since Brandi divorced me and moved in with her last boyfriend. I was not dating anyone and satisfied my kinky urges through porn and masturbations. I remain turned on by female domination, cuckoldry, and sissification. Fortunately, we live in a time when specific porn can be searched for and found. I continued to frequently wear panties under my male clothes and occasionally wear other lingerie at home. Some of my most satisfying orgasms were while sissy-attired, usually with at least my pubes and armpits shaved. I had a great orgasm after shaving my legs once. My submissiveness was limited to my sexual self, as my business continued to thrive. I’ve posted most of my adventures with Brandi, but last weekend starts a new phase of my life.
Even before I met Brandi, I had a friend who had me locked in friendzone, but she was a great friend, so I just stayed friends and moved on elsewhere (Brandi) for romance. We stayed in touch over the years, living a few hours apart. Nothing ever developed romantically, but we were close otherwise. Jace was serially monogamous, never marrying but having several long-term relationships. She came to see me last weekend. We were discussing my business and she was exploring if this would be a good idea for her to replicate near her home.
We’d finished the meeting and we were sitting on my couch having a beer, watching a football game.
Out of the blue, she made a sexually suggestive joke about one of the commercials.
She’d been using my laptop and I joked, “What? Are you scrolling my browser history?”
“Oh I’d love to see that,” she teased.
“Sorry. Incognito mode. No history.” I closed the topic nonchalantly.
Throughout the game, she would bring it up a few more times, offering in-game bets where she’d get to view my porn favorites if she was right, guessing things like run or pass, get the first down or punt. She was wrong every time, so I just laughed it off. Finally, she was right once, pumped her fist and exclaimed, “now you gotta show me your kinkiest stuff.” Jace had a look in her eye I hadn’t seen before.
I dismissively shook my head and grabbed the empty beer bottles to get another round. As I stepped past her, while reaching for the last empty, I felt her grab the back waistband of my gym shorts. She quickly pulled them to my ankles, and I stumbled. I scattered the bottles on the coffee table, and I landed over her lap. Without hesitating, she started spanking me and didn’t stop.
“I’m going to keep spanking you until you agree to show me your porn favorites.” She wasn’t kidding; she just kept going. Her off hand was holding me down, but I really stopped resisting after the first few spanks. Finally, I said uncle, agreeing to her terms and she let me slide off her lap onto the floor. I winced as my reddened ass hit the hardwood floor. I scrambled to pull up my shorts, simultaneously grateful I wasn’t wearing panties and horrified to notice how hard my cock was. I struggled with my shorts the last few inches due to my hard cock.
“Wait, wait wait,” she said as I stood up, staring at my crotch. “Are you shaved?” She yanked my shorts down again. It might have been better if I was fully shaved, but I had left a very feminine little spot of spot of hair curls above my penis. I’d also gone into the tanning booth at the gym with a skimpy thong panty on, so I had cute, ultra-feminine tan lines. I had been thinking about posting a picture online and was getting it set up to be especially fem.
Her tone became firm. She handed me my laptop and just said, “Now.”
I logged into Literotica and let her read all my Brandi stories and scroll thru my favorite authors and stories. I kept her drinks coming. There were a few times she gasped and touched herself. The tension in the air was palpable.
When she was done, she closed the laptop gently, looked at me in a commanding way and said, “I’ll be spending the weekend.”
She took me by the hand and led me upstairs to my bedroom. We stood in front of the dresser, and she had me show her every pair of panties, lingerie and dresses. She was especially intrigued by the garter belt and sheer stockings, holding them up to the light and nodding in admiration.
She pointed to the master bath and simply asked, “next?”
We walked in and she had me open the cabinets and show her my skintimate shave gel stockpile and Harry’s razor inventory, which is admittedly impressive if you are inclined to a sissy life. She also noted the disposable enemas and bottle of Viagra. ‘She handed me a pill and had me swallow it. “Let’s hope that’s not the last thing you swallow tonight,” she giggled. “Take your clothes off.” She walked back to the bedroom as I stripped. I heard her talking on her phone but could not make out what she was saying. She came back in holding her cell phone and I realized she was snapping pictures of me and I instinctively covered up with my hands, but I’m sure she got several shots before I did. She took a firm hold of my balls and whispered,
“Never cover yourself from me or you’ll regret it.”
“Yes, uh yes ma’am” I stuttered in reply.
She ran her fingers through the hair on my chest, then down my legs and back up to my ass. “Gather what you need and get in the shower and remove all that body hair; you can leave this.” She tugged on my pubic curl patch.
“Which are your favorite panties?” she asked from the doorway.
“I guess the pink ones.”
She laughed. “Half of them are pink, sissy.” My hard cock jumped as she called me sissy. She noted as much and smiled.
I stepped in the shower while she stepped out of the bathroom. It took a while, but I emerged from the shower nearly hairless, with just that Marilyn Chambers style pubic puff. I dried off and applied the lotion I found on the vanity, left there by Jace. It had a flowery scent and it felt smooth on my hairless legs and chest. There was a chair in the middle of my bedroom and Jace gestured that I should sit in it. She straddled me and delicately put some makeup on my eyes and cheeks.
I didn’t realize anyone else was in the house until Jace’s long time best friend Elin weighed in. “I always knew you were a sissy. I told Jace years ago we should have our way with you.”
“She did,” Jace told me. “She noticed your submissive side years ago. I never believed it until today. We might have to punish you to make up for all the years of fun we missed out on.”
They dressed me in my white sheer stockings, garter, pink lace panties and white baby doll nightgown. I would be serving them the rest of the night. They ordered food for delivery and tried to get me to open the door but I squealed, ran and hid in the kitchen when the doorbell rang. The women followed me into the kitchen with the delivery driver, so my strategy failed and I was face to bright red face with a handsome delivery driver who eyed me up and down, with a weird grin on his face.
Jace stood next to me and had one hand on my shaved ass cheek and asked, as if to the whole room, “so I noticed a lot of bisexual themes in your stories. Have you ever actually been with a man?”
I was speechless. Elin chimed in. “You know. Sometimes your deepest fear is really your secret wish.”
Jace led me over to him and put my hand on his crotch. I felt him grow. He leaned in and kissed me, putting his hand over mine and helping me rub him through his pants. One of the women lowered his pants. He seemed to be wearing silk briefs — panties possibly — but not nearly as feminine as mine. My hand slipped inside his silky bikini and ran my hands over a smooth set of balls, returning to his shaft, but without the silk now, which had fallen to his ankles.
I felt hands on my shoulders pushing me gently down and I reflected on Elin’s words about deep fears being secret desires and I thirsted for his cock. I kissed the head and licked up and down the shaft like a popsicle. I licked his balls, holding his cock upward. I came back up and engulfed his entire shaft, taking him deep in my mouth, nestling my lips at the base of his cock, noting his much more masculine style grooming. I was proud of my ability to take all of him, and the women commented on how much of a natural I was. I gently caressed his cock with my mouth and tongue slowly, savoring the moment. He was moaning in pleasure.
“What a good cocksucker you are.” Jace commented. “A natural.” At the word cocksucker, my own cock twitched in my panties.
Jace pointed it out to Elin. “Did you see his tiny cock twitch when I called him a name? I wonder if we can make him cum just from our words.”
The cock in my mouth was pumping with more urgency and I fondled his balls as he pressed with assertive force into my willing mouth. He tensed and erupted in spurts that filled my mouth. I swallowed what I could and dribbled much of it onto my frilly clothes. I kept him in my mouth as he softened, gently cleaning his beautiful cock.
“Did you see how excited his tiny cock got?” Jace asked Elin.
“He is such a good sissy cocksucker.” She replied.
“His cheeks are still pink from his spanking earlier. I can’t wait to peg his shaved ass.”
As they spoke about me in degrading terms my cock kept twitching in my lace panties and I erupted, filling them with cum. The women squealed in delight as they saw this.
It was still only Friday night.