tagTranssexuals & CrossdressersI Learned My Lesson Well Ch. 02

I Learned My Lesson Well Ch. 02


As I told you in part 1, Angel really taught me a lesson regarding cumming without her permission. I was so grateful that I hadn't lost her to a superior black stud, I was even afraid to masturbate to porn on the internet.

We have two computers, hers and mine, next to each other in our office. She told me she had forwarded an email to me from one of her girlfriends, but I hadn't received it, so I decided to check the email on her computer to find it. What I saw made my heart stop. There, on her list of emails received was an email from her black master Ron. I cautiously opened it.

There was an email from her to him with his reply below it. It read;

Dear Master-

"I can't stop thinking about you and the wonderful weekend we spent on the coast. My cunt is still stretched out from your beautiful cock. I have never had children but I know giving birth must be close to the sensations I feel when you fuck me. I would so much like to taste your cum, and feel you inside me again, however, I made my fiancé a promise and unless he cums without my permission, I must remain true to my word."

Your Black Cock Slut

My Sweet Little Slut-

"I too have been thinking about you and our weekend together. Actually, I have been viewing it on my big screen. You see, I videoed it without your knowledge. I have been showing it to some of my buddies and they really want to meet you. Think about it. All the cock you could ask for, in your mouth, your ass, your cunt, cumming all over you, hands touching you, squeezing you, men lined up waiting to tease and please you. It's just a matter of time until your little wanker spurts accidently, and then you are mine again. Try not letting him cum for a couple to weeks."

You're Master Ron

"Oh my god!" I thought, "She loved it! She still wants it! He can give her what I cannot. A big hard cock, actually, many big hard cocks. I know it's not fair to deprive her of this, but what if I lose her? No I cannot give her my blessing, even though she needs and deserves it. It is too risky. I cannot lose the love of my life. Maybe I should buy a big black dildo. No, she doesn't like plastic in her. Such a purist."

I kept picturing them together, her, him and his buddies. I kept thinking of the things they would do to her, how much she would like it. My cock grew hard. I rubbed it with the magic wand and visualized her being gangbanged. And then to my utter horror, I came.

"Oh no!" I thought "Not again! How could I let this happen? I'm a fool, an idiot! I don't deserve her."

Angel could tell when she got home that something was wrong. She guessed the problem immediately. "You came again, didn't you?" She asked accusingly.

"Yes," I sadly admitted. "I saw your email from Ron; I started visualizing you two together. I imagined you being gangbanged by him and his friends. It just happened, I couldn't stop it." I meekly replied.

"Fine." She said. "Just the excuse I needed to see him again. Thank you, I want you to call him and tell him you came without my permission, and then beg him to fuck me and ask him to invite his friends. Tell him you will, drive me there and give them any assistance they need, like, sucking them hard while they waiting, cleaning my cunt after they come, getting us drinks, refreshments or anything else they request, got it?"

"Yes dear." I meekly replied. I felt totally humiliated. Not only was my true love going to get gangbanged by her black lover and friends, but I would have to arrange it and even help out.

"Now," she said, "I'm really horny and can hardly wait to get good fucking from my black studs. Set it up for this weekend." She handed me his number.

I went to the phone; totally defeated I called her black lover. No answer. I started to leave a voicemail. "Hello, Ron, this is Angel's fiancée; I lost control today and came without her permission. Angel wants me to set up a gangbang for her with you and your friends this weekend and to volunteer my services as you seem fit..." I heard his deep masculine voice interrupt my message, "Well, hello there little sissy, just couldn't keep it under control huh? Good. I knew it would be just a matter of time, I sure missed your lady, or should I say your mistress. She's way too much woman for you wimp, but I guess you already know that, don't you? Well, tell my black cock slut to be at the address I email her at 8pm, Saturday night. You too. I want her shaved, heavy slut makeup, and tell her to just wear a trench coat, nothing else. As far as you're concerned, I want your cock caged, body shaven, panties, bra, garter belt, stockings, heels, wig and full makeup. My boys love to have their cocks sucked by a sissy wimp white boy maid!" he laughed and hung up the phone.

Angel made me sleep on the couch for the next two nights. She wanted to get plenty of rest for the weekend and didn't need a wimpy little sissy wanker interrupting her beauty rest.

Sleep for me was impossible. I couldn't get the upcoming weekend out of my mind. Friday morning, Angel came in and sat down next to me on the couch.

She started speaking to me is soft, loving tones. "Listen darling, I want you to know that I love you more than anyone in this world. You have so many qualities I admire in a man. You also have this dark side that we need to address, the side of you that is submissive, the cuckold, sissy wimp that longs to be humiliated. I have no problem with these fantasies; I just want to be part of them. I don't want you jacking off and cumming to the porn on the internet so there's nothing left for me," She continued, "I think we need to explore these fantasies of yours. Maybe the reality of you seeing me actually being a slave to these black men, while your dressed in drag being humiliated by sucking them hard and eating their cum out of my pussy, will get this out of your system. I plan on making this weekend as humiliating as possible for you, if you still long for this abuse after this weekend, maybe we can arrange something more permanent. I promise you this. No man can ever take me away from you."

I felt the tears running down my cheeks as she spoke. Maybe she was right. Try it for real and see if it is something I really want.

"OK sissy, put on your cage, panties and jeans and T-shirt, we have a busy day. First stop, the beauty parlor."

I felt so embarrassed going into the parlor with her. I had been there before to pick her up and they knew me as her macho boyfriend. No we were both were scheduled for full body waxing, hair, makeup, pedicures, manicures and ear piercing.

Angel told them to "make it as embarrassing as possible for me."

The Beautician, Mary, laughed and said. "Don't worry; this is going to be fun. The girls and I love to put little sissy wimps in their place. The customers will get a kick out of it to." She then took me by the hand and led me to an open stall that was visible to everyone in the salon. There were four other staff present and five women getting various services done for the weekend. Everyone seemed to know why I was there. "OK sissy," Mary said, "strip!" I took off my jeans and t-shirt and stood there in my panties and cock gage blushing from head to toe, enlisting laughs and giggles from the women in the salon.

"Oh how adorable!" "Isn't she cute!" "Not much in the cock department, I can see why she is feminizing him!" were a few of the comments I heard from the female staff and customers.

First the body wax. Very painful! It seemed go on forever. When I was totally denuded of all body hair, except for my eyebrows and hair on my head, I felt so naked, vulnerable and exposed.

"She looks much better that way." "Yes, sissies shouldn't have hair, someone might mistake them for a real man." two of the ladies said, causing laughter throughout the salon.

Next, my hair. My eyebrows were plucked into a high feminine arch and then my hair was died a strawberry blond and cut in a very girlish styled with tight curls and bangs. Then, full makeup was applied, giving me a rather sluttish look. This is going too far! It felt strange not having a beard and mustache after 20 years. I was so humiliated; I could feel the tears starting to run down my face.

"Oh don't cry sweetie, you will spoil your makeup and we will have to make it more permanent." said Mary.

I quickly pulled myself together. Next, my nails. Fake nails were glued on and a hot pink polish was applied to both my fingernails and toenails. Finally my ears were pierced and large hooped earrings were placed in each ear. I looked ridiculous. Some men can pass as women. I can't.

I looked like a sissy faggot drag queen. Angel looked stunning from her make over. I had never seen her look so sexy. She smiled when I was paraded around the salon while I thanked each of the women and tip them for making me look so feminine.

Next stop, clothes. Angel took me to a woman's clothing store that also catered to transsexuals and transvestites.

She explain that she was "going to cuckold me this weekend and she wanted me to look pretty in a sexy maid's outfit while I server her and her lovers."

The other women in the store seemed very amused and congratulated her for having me so well trained. Again I was told to strip, this time completely except for my cock cage. This drew snickers from the other ladies in the store and my cage was fondled and my butt was pinched as went from table to table picking out my attire for the weekend.

Angel didn't need any clothing because she was instructed to wear only a trench coat. I would be wearing black panties, bra, garter belt, stockings with a frilly white apron and maid's hat.

"This is going to be a weekend we will never forget!" Angel said, as she put a collar around my neck and let me to the car.

To Be Continued...

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