“Mom, what am I going to do about Jason?”
My daughter sat facing me seated at my kitchen island with a troubled yet familiar look upon her face. It was the same look I’d seen when she was doing poorly in a class or when one of her friends slighted her. The circumstances were quite different this time, however.
She was thirty years old and had just found out that her new boyfriend was a racist, homophobic scumbag. Oh, he seemed nice enough. He’s handsome, has his own home, a nice car and truck. I’ve seen him around town for years on big billboards touting his family’s real estate business.
When Robyn told me that Jason had asked her out, I was probably as happy as she was but that quickly changed when she brought him over to my house before their big first date. And it was a good thing that he showed his true colors at that point. I knew my Robyn and I knew she wouldn’t hold out very long. Just like me, if she was attracted to a guy, she was going to fuck him probably sooner rather than later.
“Oh, Hell, sweetness, this isn’t even an issue,” I told my teary-eyed daughter, “you dump his sorry ass now.”
“You’re right Mom, as usual.” Robyn sighed.
The incident had been an ugly one. They came over for a short visit on their way to an awards function that his company was having. They came in through the sliding glass passing through the dining area and into the kitchen where I was setting out cookies and pouring coffees for us.
“Mom, this is Jason. Jason, my mom Janine.”
I smiled at the man and held my hand out to him and received nothing more than an icy stare followed by averted eyes.
'Ok,' I thought, trying to give him the benefit of the doubt, 'maybe he sucks at social cues.”
I knew at my core that this was not the case. I was used to that look having lived in the same small southern city my entire life. He had just given me the, “Holy shit it’s a Tranny," look that I’d received so many times over the years. I was married for six years in my twenties, a union that produced my beautiful Robyn whom I love more than my own life.
My ex was in real estate as well and she did very well for herself. I thought to myself that maybe this was my in. I hoped that I could win this guy over.
“My ex Sarah Patterson is in real estate too. I’m sure Robyn told you,” I said, still getting the daggers from him, “do you know her?”
“Yeah, she’s with Patterson-Hanks on the south end. They do a lot of low-end apartment management and cheap houses. They deal with the Mexicans more than anyone else in town,” he said with a look of disdain.
“Well,” I said, my smile gone, “everyone needs housing, right?”
He placed his palms flat on the island countertop and gave me one of the most hate-filled looks I’d ever encountered and said,
“Oh, sure, honey, let’s just fill our town up with anyone or anything. A lot of us here are sick to death of all the immigrants and the perverts.”
Robyn stood there with her mouth wide open, searching for the words, any words to tell this creep off. All that she could muster was gasping sounds. I, on the other hand, had only one thing to say.
“GET, the FUCK out of my HOUSE!!!!”
He strode out past Robyn and I as we stood there in shock. I had to sit because my knees were trembling so hard, I thought they might buckle. Robyn ran into the living room and peeked through the drapes to mask sure the jerk was gone. She came back into the kitchen, eyes wide, her hand still over her gaping mouth in disbelief.
“Oh my God, mom, I’m so sorry. I had no idea that he was like that,” Robyn said as she hugged me tightly.
“It’s ok, hon. We never know until we know.” I said, the smile returning to my face.
After coffee and some of my world-famous tea cakes that Robyn always loved so much, we chatted through a couple of romcoms. As much as I hated the circumstances that brought her here tonight, I was so happy for our time together. Mom/Robyn time had been in short supply lately and I had missed it so. After the films and refreshments, I drove her back to her place. Before she got out, she turned to me and said, “You know, I’m so fortunate.”
“How’s that, honey?”
“I have friends who don’t get along with their parents at all, and here I am with two of the best moms in the world… and both of you have my back through anything,.” Robyn said, her eyes tearing yet again. As I drove home, I thought about my ex. In many ways she made me the gurl I am today.
To be honest, my marriage to her was wonderful at first. I thought I had put my crossdressing proclivities behind me when I married Sarah but soon the urges came back to the surface. She was (and still is) an extraordinarily lovely woman and being in such close contact with her clothing and shoes and lingerie and makeup was too much for me to bear.
At first, when she caught me, I was scared shitless, then I was overjoyed to discover that she was way into it. She loved to feminize me. She reveled in shopping for me and buying sexy teddies and baby dolls, hose, and panties for my own collection.
We would dress every night and have the sweetest most passionate sex imaginable. She loved to kiss and cuddle and to have me go down on her for hours. She also loved the rougher stuff as well. Oh god, did she love it! I spent many nights face down, spread eagle, tied to the four corners of the bed while she beat my ass raw with her riding crop or hairbrush and then savagely fucking my ass with her big goddamn strap on.
The problems were there, just under the surface, but we were young and horny, and they didn’t manifest for a time. The main turmoil really was that I wanted to be fem 24/7. She, on the other hand, wanted a traditional man-woman relationship in public. And much to my disappointment, at the time, my cock wasn’t large enough to totally satisfy her.
This isn’t a problem for me now and hasn’t been for some time. I love my petite she-cock… and so do the guys. It was, however, a major concern in my youth, and I compensated with long sessions of oral and dildo fucking. She loved that but I could sense that she really wanted a cock that made her squeal.
So, we got into threesomes with a friend of mine from work, a handsome as fuck black guy named Thomas who had (and still does) the most amazing cock. And we both fell for him. He has the greatest stamina of any lover I’ve ever had, and he would fuck Sarah so deep and so hard and for so long. It was a magnificent thing to behold seeing this ebony Adonis fuck my lovely bride.
I’d lie beside her pinching and kissing her pert nipples and soul kissing her hot mouth as she whimpered and screamed into mine. After he came inside her he would present his cock to me. I would suck and lick it clean before he retreated to the other side of the bed to watch the show. I would kiss my beautiful wife for a minute, just to share the resplendent juices I had just gleaned from his throbbing shaft and then I would go down on her.
I absolutely loved the taste of her pussy mixed with his salty cum. I can taste it to this day. I would lose myself in Sarah’s pussy, licking and tonguing like a good girl as she moaned. It took a while to bring her to orgasm after having been fucked by Thomas, but I was so into it I didn’t mind one bit. And watching Thomas’s cock start to twitch and grow again was always so beautiful.
I would reach over and stroke him slowly, squeezing and pumping his huge member as I lovingly kissed and sucked Sarah’s steaming cunt. When they started kissing my passion grew exponentially… how I loved them both.
When he was rock hard, he would move behind me and lube my puckering fuck hole and start rubbing the head of his massive throbbing cock on it. My moans and whimpers would match Sara’s as he impaled my tight pink asshole with his manhood. Soon he would hit his stride, fucking me hard like he did my loving wife, although it seemed to me that sometimes he fucked me harder.
The thrusts pushed my mouth and tongue into her streaming snatch and she and Thomas would usually cum at about the same time. Back then I rarely came from anal so I would lie on my back, cum leaking from my cream-pied boy pussy as Thomas and Sarah sucked me. The love we made and the orgasms we all had there in our bed were some of the best of my life… of our lives.
There were so many memories on this cool autumn night. I am an innately positive person and I’d successfully pushed the negative feelings I had earlier to the back of my mind. I made one quick stop at a friend’s house and bought some really great weed from him and continued on. My little weed detour caused me to head home the back way by a small park that takes up the whole block behind my house. Driving by the park on that street you can see my house through the trees if you know where to look and I usually glance, even at night.
I saw his car there in the parking area under one of the streetlamps. I knew it was his because there aren’t too many blue Jags in our town.
'Ok,' I thought, 'that fucker is either trying to see if Robyn is still there or he is skulking about waiting to do something to me.'
Either thought was disturbing, but I wasn’t frightened. I’ve been stalked before and I don’t go anywhere without mace and a pistol in my purse. That’s right. I’m the biggest bleeding heart in town but I am quite aware of the number of women, especially trans women who suffer violence at the hands of men. And mine is an open/concealed-carry state. I am permitted and packing always.
I rounded the block and pulled into my drive. I checked my weapon, cut the lights, and sat there for a minute. If he was going to make a play here, I wanted my eyes to be acclimated and my pink gel tipped finger on the trigger. I saw no movement, so I got out and strode confidently to my door… quick positive motions… eyes alert, head moving about, listening intently.
Once inside I took a quick pee, washed my hands really well with scented soap, checked my hair and makeup, stuck my Glock down the backside waistband of my Boyfriend jeans, and turned and looked in the glass. It wasn’t even visible through my tunic sweater top. Satisfied, I went back into the kitchen to make tea. As I set the kettle on the boil, I saw his form move by my window in my periphery.
'Ok Janine, this is it,' I thought.
I didn’t know what this guy was up to but the only thing in all this that I was certain of was that this asshole would never hurt my baby again.
Tap, tap, tap. His knock wasn’t loud or angry but insistent none the same.
“Who is it/” I called in the most unconcerned sing-song tone I could muster.
“It’s Jason… is Robyn here?”
I went to the door, unlocked it, and slid it open a crack with my left hand, all the while resting my right on the Glock behind my back.
“Now Jason, you were told to leave. And I think you know full well Robyn isn’t here. What is it you really want?”
“W-Well,” he said haltingly, “I wanted to apologize for what I said earlier.”
I slid the door open, showing no fear or hesitation and you could tell that move surprised him because he stepped back a step.
“Well come in,” I said motioning toward the kitchen.
He walked silently in front of me and I studied his form from behind. He was at least six-foot-two and did not appear to have an ounce of fat on his body. He was mid-thirties with perfect slightly graying blond hair and from the back, I could see that he did not have the thinning spot on the back of his skull that so many guys had.
'Either he has good genes or a great transplant clinic,' I reasoned.
We reached the kitchen island and he turned around,
“Well, like I said I just want to apologize for what I said earlier.”
“About the immigrants?”
“Well… I was raised a certain way. My parents are very biased. I wanted to apologize to you.”
I wasn’t impressed. I don’t like bigots point-blank. And he made no bones about his intolerance. I was certain that the only reason he was apologizing to me was that he was trying to get to Robyn. I decided to feel him out while I figured out what to do. He and his family were some of the wealthiest most influential people around.
Their real estate business, as expansive and lucrative as it was just a cog in the machine that was their empire. They owned manufacturing facilities, a large telecommunication center, a building supply, several restaurants, gas stations, and more land than you could shake a stick at.
I was pensive. “Apologize for what, then, Jason? For the pervert remark?”
“Well, yeah,” he said, crossing his arms and raising his head slightly so as to be looking down his nose at me. You could tell he rarely apologized and that when he did, he expected it to be accepted without question.
“Well, to be honest, Jason, I don’t care what your estimation of me is nor am I seeking validation from you… I do however have many close personal friends who are of minority or immigrant status and your statement bothered me.” I said. “These people deserve fair housing practices, the same as anyone.”
You could tell that he wasn’t used to being challenged. He shifted his weight uncomfortably, uncrossed and then recrossed his arms while he tried to formulate a response. It took him a few seconds…
“Hey, listen,” he said holding his hands up, “things have always been done like that here. It’s the way I was raised.”
“Well, Mr. Jason,” It was my turn to cross my arms now. “I was raised in a bigoted home as well and I took more than a little shit from my family for refusing to go along. When I was old enough to leave, I cut the bigots out of my life and kept the ones who evolved.”
“I'm not here to argue race or any of that,” he pleaded, “I’m just here to apologize to you.”
My eyes narrowed as I edged even closer to this pompous ass,
“Let me promise you one thing Jason, you can apologize to me until you turn blue, but I will never, ever, give my blessing to you dating Robyn.”
He stepped back a step and stuck his hands into his pockets and dropped his gaze. The motion was as that of an embarrassed teenager. Keeping his eyes down he said,
“I’m not here for that either, although I don’t want Robyn to have hard feelings against me. I’m apologizing to you because I think you’re really pretty and I’d like to know you better.”
And there it was. I have to admit that even I didn’t see that one coming. It was not at all unusual, here in the deep south. I’ve been hit on a thousand times here by “straight” guys. My girlfriends jokingly call me “The Heartbreaker”. Guys who would talk all kinds of shit about me at their jobs or around their friends would, in private, worship the ground I walked on.
And here was another. I could easily have him, but he was an abhorrent human being.
'But what if he wasn’t?' I asked myself. 'What if he could be persuaded to evolve?'
I had a plan working in my head and I weighed the pros and cons as we stood there in my kitchen. Here was this young man, wealthy and hot. He was also a bigoted, homophobe with an innate sense of entitlement. What could I do? Left to his own devices he would remain a narcissistic asshole. I was going to exact a bit of punishment on him for damnable ways and maybe change him in the process.
I edged toward him, looked him straight in the eye, and purred, “So, you really think I’m pretty?” I asked while executing my sexiest hair flip.
“Yes, I do, Janine,” he said.
I could see his cock shift in his slacks.
“It looks like someone is glad to see me,” I said as I reached out and brushed my pink stiletto tipped nails on his growing member.
He sucked his breath in sharply and embraced me. We locked eyes for a moment and then he pulled my close. Our lips met and his tongue probed my hot mouth lustily. I could feel the stiffness of his throbbing cock as it rubbed against my belly. I have to admit that I was feeling the tension as well. It had been a month or so for me since I’d had a lover.
