Journey of the Whiteboi

Ch. 2: Meeting Virginia!

As I jumped in the shower, I did hope that she wasn’t disappointed by what she found. Through a trick of genetics, I was small at 5' 3" and a buck-twenty with not very much to say about endowment or muscles as I had already mentioned. I shaved the stubble off my face, then brushed my platinum blond hair and teeth. Since it was a warm afternoon, I put on a pair of cutoffs, a T-shirt, and bobby socks. Then, I broke out my Drakkar Noir aftershave and splashed a little on. I glanced at myself in the mirror from side to side and bobbed my hair. I looked good and I was ready to go, so I donned my sneakers walked out the door locking it behind me, and jumped feet-first into the great unknown.

I had no idea what to expect from this situation or this woman I was going to meet. A year ago, I never would have agreed to a meeting with another woman let alone one I’d met not long before in a chatroom online. But that was then and this is now. Now, I was past missing my wife and was lonely because she was away so much with her work. She had been away so much lately that there were times when the two of us were virtually strangers and we had to reacquaint ourselves with one another.

Having another person’s companionship would be good for me I reasoned as I walked along. I knew it wasn’t going to turn into anything, but to be invited out by a beautiful woman to do anything was a thrill. It had been such a long time since I’d gone out for coffee, I was looking forward to the whole experience.

As I expected, it only took me about fifteen minutes and I was standing on the threshold of the First Cup on 4th Cafe, the scent of the freshly roasted and ground beans emanating from within was heavenly. It was a decent neighborhood coffee place, depending on the locals for survival. They had a good variety of coffee and snacks. The clientele seemed to be at least semi-intelligent. I’d been coming here since we moved in some years before for the ambiance and the coffee. I also liked the fact that they were locally owned and not part of some big, multi-national chain, and the proximity to our place kept me coming back.

I purchased two coffees and selected one of my favorite seats in the whole place, an unobtrusive booth at the back of the shop where conversations could not be eavesdropped on easily. As I sat and contemplated my cup, I started to wonder what I was doing here and whether this woman was even going to show up when in the door she strolled. She was unmistakable and even more gorgeous live than she had been in pics and on cam. She wore a white, fur-lined coat with a faux fox collar, a shocking pink halter top with a matching pink miniskirt, and four-inch, clear plastic heels that made her appear taller than she was and there was a leopard print clutch purse in her hand the big sunglasses tucked into her hair rounded out the ensemble, it took some effort not to sit there with my mouth agape.

She cast about looking for me, so I waved when she looked in my direction. She smiled and cruised on over to the booth with all eyes in the shop on her, where she sat and with whom. I stood up as she approached, “You must be Dan?” she smiled, “Great to meet you!” as she extended her hand with a gorgeous smile.

“Yes Ma’am, I am, you must be, Virginia, pleased to meet you as well,” I smiled as I waved my hand over the booth I had commandeered, wordlessly asking her to take a seat.

“I love your snow-white skin!” she giggled as she slid into the booth, “And, you’ve got such a cute face.” She smiled as she interlaced her slender fingers in front of her sat her chin on them and fixed me in her gaze. The color of her large eyes was what I can only describe as liquid black, full of mystery and mischief. Her full and reddened lips beckoned to me with every word she spoke I was in danger of being mesmerized by this woman and was on the verge of blushing over her compliment as we sat down.

“It’s my Scandinavian heritage,” I mumbled, “I took the liberty of ordering you a double-double coffee,” I explained as she gazed at the cup in front of her.

“Thank you, that’s perfect!” she smiled as she unlaced her fingers and folded her hand around the cup to take a sip. She looked up at me and smiled. I damn nearly melted right there as I looked at her, I noted some beautiful gold chains around her neck and some exquisite rings on her fingers, but the left ring finger had been left conspicuously naked with no indication that a band had once sat there, I noted this piece of information and squirreled it away for later. “You’re really sweet, Whiteboi. I like the way you phrase things, I think I can work with you,” she smiled, “Since you’re new to this, you probably have no idea about what you want to do and where you want to go."

“None whatsoever,” I replied to her while gazing at her through my clear blue eyes. “I was thinking of dabbling in it a little, it all looks interesting.”

“What do you find most interesting?”

“The idea of black dominion piqued my interest,” I admitted.

“Hmm,” she intoned with a cocked eyebrow, “That should prove interesting," she giggled, "Now, the way I usually do this is to have a boi, like yourself, come to my house to learn about their newly found place in society. I help them prepare their bodies and minds for their brave, new world.”

'That sounds reasonable,' I thought, “How do you do that?” I asked, now intrigued by what she was saying and wanting to know as much about the subject as I could.

“Oh, there are various ways, depending on what is required,” smiled Virginia. “There is a fairly common theme, however. That’s just to open your mind and accept what’s going on both within and without your body. You’re part way there as it is. You mentioned that you had already experimented with your wife’s clothes, do you want to continue in that vein?”

I reddened slightly at the recollection of the comment, “Yes,” I replied quietly.

“How did women’s clothes make you feel?”

I thought for a moment before answering. "I don't know anything about it, I tried a few things on.“ The materials are more comfortable than men’s clothes,” I confessed, “I did like the feel of silk on my skin.”

She looked at me for a moment. “I didn’t ask you how they felt on you, I asked how they made you feel?”

I must have had a ‘deer in the headlights’ look on my face because her gaze softened when she saw my confusion, “Did they make you feel weak and feminine?” she asked gently, “Soft and cuddly?”

I thought about it for a moment, how I’d looked in the mirror. “All of the above, they made me feel sexy and desirable,” I confessed, "I didn’t think I looked too bad in drag, I thought I looked kind of cute."

With a big smile, “I can teach you more about it and explore it with you,” she said, “I’ll teach you hair, makeup, or whatever is needed to help you on your way.”

Oh! Well, that doesn’t seem so bad,” I remarked, not understanding what I was letting myself in for, “Can I have some time to think about it?”

Oh, yeah Whiteboi,” she smiled, “Take all the time you need, call the number on this card and I’ll come and pick you up when you are ready, in the meantime if you dress up again take some pictures and send them to me so I can see you and where you're at with your style.” handing me a grey business card embossed with a silver phone number.

“Okay,” I smiled while rising out of the booth as she did, “It’s been great to have coffee with you,” I said looking into her eyes.

“This has been fun,” she agreed, “I’m looking forward to seeing you online or hearing from you soon.”

“See you soon,” I bade as I headed in the direction of home to consider options and my next moves.

The next night, I was inexorably drawn to the chatroom. When I arrived, Virginia was in the main room discussing the pros and cons of various chastity cages with a few other women in the room. I sent her a private message saying, “Come with me and I’ll make all your dreams come true!” with a tongue-sticking-out emoji beside it.

I saw her type in the main room, “Well, you’ll have to excuse me, I have a date to go on!” She finished, then appeared in the private chat, the laughing emoji was first, and then, “Oh Whiteboi, you know how to crack me up!” The pop-up asking me if I wanted to voice, and cam communicate with her appeared on my screen and I clicked the ‘ok’ button immediately opening a channel between us, "Evening, how’s my favorite little Whiteboi this evening?” She greeted me in her melted chocolate voice that made the hair on my neck stand on end.

I blushed slightly at her complimentary entrance, I was beginning to like Virginia! “I’m in pretty good shape for the shape I’m in,” I joked, and she chuckled.

Well, I guess it’s better than having no shape!” she laughed, “On a more serious note, you are really cute, Whiteboi!”

I blushed profusely but was able to stammer out a quiet, “Thank you, you are stunning, your pictures don’t do you justice!”

"Ever sweet, Whiteboi,” she gushed. We continued talking into the wee hours of the morning. I found it very easy to talk to Virginia, maybe too easy. She was charming, funny, smart, and sexy as all hell with a very soft and accommodating attitude, and she charmed the pants off me, literally.

“Well, the time has come once again, for me to lie down and get some sack time, Virginia. As always, I don’t want to leave, but I’m falling asleep sitting here.” I explained as I yawned.

“It’s ok, Sugar, we’ve got all the time in the world,” she said, “Have a good sleep, and I’m looking forward to seeing you tomorrow!”

Now, ordinarily, I would have been questioning what such a beautiful woman would want with me, a short, underweight, little, insignificant white boi like me? I was blinded by what I thought was my good fortune so much so that I hadn’t taken a moment to look before I leapt and that was going to lead to trouble. As soon as the connection snapped off and I was gone from the chatroom, I turned on Pornhub to get my daily dose of interracial porn. I found one where a black man with a massive cock impaled some poor, screaming white chick from behind. Her blue eyes under her blond hair were facing the camera and were the size of dinner plates. He then grabbed her around the neck and looked like he was forcing more of his immense manhood into her overfull cunt. She screamed and wailed as she got pounded harder than she ever had in her life. He finally nutted in her snatch and then flung her aside like yesterday’s fish. I blew my load as the scene ended, cleaned up, and went to bed. It began to occur to me that no other porn had ever gotten me off like interracial and that I wasn’t turned on by any other sort of porn anymore now that I had discovered interracial. I looked down at my flaccid, pink clitty as I thumbed through other porn images, without effect. This night, I dreamed I was walking in a forest of big black cocks when suddenly, they were all chasing me, half bent on getting me to give them head and the other half determined to fuck me, I awoke with a start. “Wow, weird dreams I’ve been having lately,” I thought as I rubbed the sleep out of my eyes, got up, and prepared to start the day.

After having a shower and brushing my teeth, I went downstairs and made myself some pancakes for breakfast, then got my day started. My wife was coming home tomorrow afternoon and I wanted the place spotless for when she walked in. I worked diligently all day cleaning the house, re-sheeting the bed, vacuuming, and mopping the floors, and then laundry. 'It’s in pretty good shape if I do say so myself,' I thought as I looked around. I was pretty proud of my efforts and rewarded myself with a homemade coffee.

At about eight in the evening, I jumped on my computer to see Virginia, who was quickly becoming one of my favorite people. She wasn’t there right when I got there, so I settled down to wait. I didn’t have to wait long. Her screen name appeared soon after and I sent the invitation to a voice conversation, which was immediately accepted.

“Hi, Whiteboi!” came her beautiful voice through the speakers, “How are you doing this evening?”

“Hi Virginia, great to see you, as always!”

She giggled, “Always the sweet little Whiteboi!”

"My wife comes home tomorrow afternoon, and I want to spend some time with her, so I may not be around for a day or two, okay?”

“That’s great, Hon, you two have a great time.”

As had become our custom, we talked well into the night again. She was beautiful all over, mind, body, soul, and heart. By this time, after the other secrets I’d shared with her, I trusted her and would have done anything she asked. “You bet I do,” I smiled, "Maybe the next time my wife goes away to work?”

“That sounds fantastic! Have a good sleep, Whiteboi, chat with you soon!”

The next porn I found to my liking was one of two big, black alphas dominating a little white sissy’s sweet ass. Like I said, I’m not gay, but that scene made me hot. The whiteboi had a cute, well-made-up, feminine face and was wearing a very short blue skirt with white, lacy fringe. His legs were covered in white knit, thigh-high stockings, and a pair of white, Mary Jane shoes covered his feet. His bouncing little clitty was encased in a metal cage. A pink halter top that was gone soon after the scene started stretched across his chest. There were two huge and very well-hung black studs dressed up in police uniforms to fill out the cast. As it opened, the sissy was walking down the street. “Stop Sissy!” a masculine, black voice called out, two large black individuals in police uniforms approached him as he turned around.

“Is there a problem, officers?”

“Just a routine check, Ma’am,” said one of the officers, ID, please. The sissy reached into his purse and brought out a card one of the officers took the card and worked with his iPad for a moment.

The other cop looked at her, “We’ll do a clothing check here too, lift your skirt!” he ordered, “I need to check your cage!” The sissy hopped to and lifted his skirt, exposing his milky white thighs and securely caged clit. The officer took the cage in his hand and manipulated the sissy’s genitals for a moment. “Good and tight,” he said, checking the item off the list.

“You were convicted of not doing your service to the BNWO... cock sleeved, and sentenced to community service!” The other officer’s face was frightening as they both put a massive hand on the back of his neck, shoving him forward. “Let's go somewhere private so he can perform some more ‘community service!” one cop chuckled to the other as they led their prize away.

They led him down an alley before forcing him to his knees, “I got something you can service, whore!” roared the cop as he stood in front of his prize and unzipped his pants dragging out his massive member. He snaked his massive paw behind the sissy’s head, ferociously gripped his hair, and pulled his face toward his manhood. “Open up, Bitch!” he said as he fed the massive head of his big, black cock into his mouth.

“Oh, that looks good!” smiled his partner as he unzipped his trousers and prepared for his turn. He positioned himself behind him, seized his hips, and lifted him to his feet then flipped up his skirt. He glanced down and saw the sissy’s white legs and pink asshole then grunted approval. Tightening his grip, he plunged into his pink, little boi pussy while his partner was halfway down his throat. The two black alphas fucked the little snow sissy between them mercilessly. As they plunged in and out of him, the joy she was experiencing was quite plain to see, he appeared to be enjoying himself with all the moaning, groaning, and other sounds he was making. Then suddenly, the man who was fucking her face stiffened then jerked his massive wang out of the sissy’s throat, and began to spurt great gouts of cum from the tip of his magnificent black cock all over the kneeling sissy’s face. The sissy closed his eyes, opened his mouth, and stuck out his tongue, trying to catch as much as he could.

I watched almost mesmerized by the action on the screen until I fountained all over cumming with five or six strong bursts, wasting my seed all over my legs. I then cleaned up from the evening’s fun and frolic, brushed my teeth, and crawled into bed. I fell asleep almost immediately and again, the strange dreams were upon me. I was a sissy this time and I was taking my first BBC up my ass. He had a giant cock which seemed to fit in wherever he put it. There was cum all over my ass and face, but I smiled through it. I awoke in the morning with the scene still vivid and fresh in my memory. 'I’m becoming more and more gay all the time,' I thought with amazement as I found a damp spot on the sheets.