Sold By Mother Pt. 01

I turned 18 years old in February and graduated from high school the following May. I was still living at home and due to tight finances was scheduled to attend a free, local, community college. My mother and I were the only two in the house as my father had left us many years ago. There was a substantial mortgage on the house we lived in and the two of us just barely got by on what my mother made.

It was just two weeks after I had graduated high school when my mother called me into her bedroom.

"Tommy...Will you come into my bedroom right now." Called my mother.

I went into her room which was just down the hall from mine and found my mother standing at the end of her dresser wearing only her bra and panties. The drawer in her dresser that held all of her lingerie was pulled open.

"Don't look so surprised...It's not as if you have never opened my lingerie drawer before...is it?" Asked my mother.

"What do you mean?" I answered.

"Oh come off it...I've known for a long time that you have been playing in my lingerie...Don't try to deny it." Said mom.

"Okay...Maybe you're right...What is the problem with that?" I responded.

"Honey...these items are very personal to me. They touch my most intimate parts. What have you been doing in here?" She asked.

"I just look at your pretty panties and slips and I try some of them on when they fit me." I said.

"I thought you had been putting them on. You have a fairly slender body for a boy." She said.

"I just enjoy the way I look when I wear your lingerie." I said meekly.

"Then let's have you take off all your clothes right now and when you are naked you can show me what you do in my lingerie drawer." Ordered my mom.

I slowly took off all my clothes and stood naked in front of my mother who was still just in her bra and panties. With her lingerie drawer pulled open and all of her pretty lingerie visible, I tried to control myself getting an erection.

"Oh my...You have little to no hair on your pubes...And no chest hair at all...And darling; that little thing between your legs is one of the smallest cocks I have ever seen on a male. It's not a surprise you find wearing my panties to be more comfortable for you. Now go on, show me how you pick out which of my panties to wear." Said my mom with a smile.

I felt myself gaining control over my penis as it began to soften. I sorted through her panty stack until I found her full cut rumba panties that had lace around the leg openings and several rows of lace across the butt. I pulled them on and my tiny penis fit perfectly flat into the front.

"Oh...You picked out my most sexy pair! Your father made me wear those when I was forced to suck on his cock."

"He had to force you to suck his cock?" I asked.

"Well...In the beginning he did. He forced me to take off my bra and keep those panties on. Then I had to get on my knees and suck his erection. At first I only allowed him to cum on my breasts, but he kept pushing me and then I let him cum on my face and finally after a few months I began taking his full load in my mouth and swallowing. I found I enjoyed the feel and taste of his semen more than I thought. Those panties look very natural on you and a little bit sexy."

My mother and I were the same height at 5 foot 8 inches. We weighed about the same and our body shape was fairly similar except for her hips and breasts we could fit into the same clothes with ease.

"So that's the only lingerie of mine you have worn?" She asked.

"Oh not at all...Would you like me to fully dress?" I asked.

"I would...Show me what you think a pretty girl looks like." She answered.

I next went for one of her satin and lace bras and pulled it on over my head. The two of us were now standing in her bedroom both wearing bra and panties. I noticed a wet spot beginning to show in the front of her panties but I did not say anything. Next, I selected a full coverage 6 strap garter belt in white nylon with a lace border and I pulled it on over my panties. This was followed by a half-slip lite petticoat with a 5 inch lace hem and a strip of lace up one side. I topped it off with a camisole that was nylon with lots of lace and I tucked it into the top of my slip.

"You really seem to know what you are doing." Said my mother.

Without responding I pulled out a pair of nylon thigh high stockings and I sat down on her dressing chair and rolled the stockings up neatly and then placed them over my toes and slid them up my legs in perfect style. I attached the stockings to all six straps and then stood up again.

"You did that almost better than I do! And I never noticed, you don't have any hair on your legs!" Said my mother.

"I shaved it off twice and it has never grown back. I use a razor mean for women and it seems to have cut the hair very smoothly. My underarms are also hairless using the same procedure." I said as I raised my arms.

"Oh my...I had no idea you were into this so deeply. Do you have a dress of mine that goes with this?" She asked.

"Oh course I do." I replied.

I opened her closet and selected a below the knee floral print dress that zipped up the side. I unzipped it and expertly stepped into it gathering my petticoat and pulling my arms through the top. The side zipper made it easy for me to zip it up and the fit was almost perfect.

"That dress looks better on you than it does on me!" Said my mom with surprise.

The front of my mother's panties were now obviously wet with her excitement and her nipples were very visible under her bra.

"Are you enjoying the show?" I asked.

"I really am...I had no idea you knew what to do to look so pretty." Said mom.

"Well we can't stop there...I saved enough from my allowance to buy myself a shoulder length wig and I need to finish this off by showing you me in full make-up."

"You know how to put on make-up?" Asked mom.

"Mom...All the time I had to myself when you were at work allowed me to teach and learn how to transform myself into a very pretty "girl-next-door" in your dresses, lingerie, and make-up...And I topped it off with the wig I bought."

I went to the bathroom and my mother followed and I proceeded to put a small amount of foundation make-up on my face followed by a hint of blush. I applied eye shadow and eye liner and adeptly attached false eyelashes. I finished things off with a beautiful shade of lipstick that on my naturally full lips completed my female look perfectly when my wig was in place. My mother was surprised how easy I did everything and how natural it was for me to do it.

"I had no idea you were so good at this! You look adorable, and completely female! It is impossible to tell otherwise! You have never been on a date with a girl before have you?" She asked.

"No I have not." I answered.

"Is having a girlfriend something you want? I mean, do you have girls you like?" Asked mom.

"I have girls who are friends, but I have never thought of any of them in a sexual way if that's what you mean. When I am around them we mainly talk about girl things."

"So if I am hearing you correctly, you feel much more natural being a girl...And you are without a doubt a very pretty girl who knows how to dress herself to make herself look beautiful. What about your little penis? Does it ever get hard? Have you ejaculated by pulling on it? I'm assuming you have never tried sex with another person before." Said mom.

"Yes. That's correct. I'm a virgin. But from the look of the front of your panties I'd say seeing me as your daughter has you a little bit turned on." I replied.

"Okay...It has me a little turned on. I think it is because you are so pretty as a girl. I had no idea." Said mom.

"Does this mean you'd like to have sex with girls?" I asked.

"No...Not my thing. But what happens for you going forward has me a little excited."

"What do you mean?"

"Well...Would you like to dress as a girl every day? And would you want to have men find you attractive?" Asked mom.

"It would not be honest of me if I said "no." I have had more than one fantasies where I get a man sexually excited by being with me as a pretty girl."

"And have you ever tried to fulfill that fantasy?"

"The opportunity has never presented itself, but if it did, I'm fairly sure I would not hesitate to experience it." I replied.

"Oh really? Well what if I told you the opportunity could present itself tonight?" Smiled my mother.

"How do you mean?" I asked.

"Well, my boyfriend Jack and I have been planning to have a sleepover here tonight. I am very much in sync with the way Jack has intercourse with me. He has a very manly penis that when it becomes erect is fairly thick and quite long." Smiled my mother.

"Are you saying this to get me excited?" I asked.

"Only if it does excite you." She answered.

"You know I have told you before how I approve of you and Jack being together. I also must admit I have experienced a couple of fantasies about him when I am dressed as a girl. What is it you have in mind?"

"Well I was thinking it might be fun for you and for Jack if I let you learn to suck on a male erection with me guiding you before Jack and I have sex. I could also leave the door to my bedroom open so you could hear us having intercourse and I would be a little extra vocal as he puts his thick cock inside me." Said mom.

"If you are serious about this then I am serious about wanting to experience this. I see this as a big step forward for me enjoying myself as a girl. Do you think Jack will be into it?"

"I'll phone him ahead and let him know what we have in mind, but he seemed more than interested when I talked with him before about my suspicions of you dressing in my lingerie." Answered mom.

"You told him that?"

"I asked his opinion of it and he said not to worry about it. He kinda laughed at the thought saying he pictured you would look pretty dressed as a girl; and now I can see he is right!"

With this new turn of events I stayed dressed as a girl and found a pair of flats to finish my outfit. My mother got herself dressed as we waited for her boyfriend Jack to show up. I heard my mother on the phone with Jack and she came back into the room to let me know what he had said.

"So I told Jack how beautiful you looked dressed as a girl and he said he was not surprised. When I suggested to him that we let you suck on his cock he said he was very much looking forward to it and would love to."

"Well then...I guess tonight will be a very special night for me." I smiled.

"It will honey. Now you have to remember not to make him cum. I want him to save that for inside me." Warned my mother.

"I think the experience of a male erect penis in my mouth will be enough for me for one night." I replied.

When Jack finally arrived at the house I was fully dressed and had taken extra care to make sure my hair and make-up were perfect. My mother greeted Jack and the door and introduced him to her daughter. I felt excitement as being introduced as her daughter.

"Oh my goodness! Your daughter is gorgeous! What is her name?" Asked Jack.

"Linda...Her name is Linda," my mother said quickly.

"Well Linda...I am very pleased to meet you...I'm also very flattered you want to be sexually intimate with me." Said Jack.

I raised my voice and said; "Thank you Jack...You are very kind, and I have always thought you were very handsome."

"I think he's handsome too." Said my mother kissing Jack on the lips.

"How do you want to do this?" Asked Jack.

"I thought we'd all go into the bedroom and Linda will unzip her dress and take it off but leave her pretty lingerie on. It would be best if you stripped fully naked. Then I'll direct Linda on how to get you excited." Said my mom.

"Well it won't take much for her to get me excited. She is beautiful and very sexy." Said Jack.

My mother and Jack went into her bedroom and I could hear Jack taking his clothes off. My mother took her dress off and again was wearing only her bra and panties. She called me into the bedroom and the first thing I saw was Jack's half erect, very thick, and somewhat long penis. His naked body was very manly and muscular with a fair amount of body hair. I found the sight of a naked man very sexy.

"Come on in Linda. Jack has told me how anxious he is to share his sexual pleasure with you." Said my mom.

"I'm very anxious to share myself with such a pretty girl, Linda." Said Jack.

"Okay...What would you like me to do?" I asked.

"Unzip your dress baby but leave all your pretty lingerie in place. Then get down on both knees in front of Jack's penis and I'll direct you from there." Said my mom.

I slowly unzipped my dress and slid it off my arms and then slowly pushed it down from my waist to the floor before stepping out of it. Jack's erection popped up to attention as he saw this and he was almost at full hardness before I had even touched him. I slowly got down on my knees as I gently lifted my petticoat and Jack's erect penis was directly in front of my face.

"Very good my daughter. Now reach out and gently put your fingers around Jack's cock and lick the helmet of his big erection." Directed my mother.

I did as she asked and for the first time in my life tasted the head of an erect male penis. I immediately found the taste enjoyable. I felt the tip of his cock being a little wet and I later found out that was pre-cum. Jack gave out a delightful soft moan.

"That's good honey...You're doing great. Now take the entire head of the penis and put it in your mouth with your lips gently touching the underside of the helmet rim. And use your tongue to lick and tap on that big cock head." Said my mother.

Again I followed my mother's instructions as she watched, and Jack began to moan even louder before saying;

"Ohhhh baby! You feel so good. You are a natural cock sucker. You are without a doubt a cock sucking girl."

"You're doing great my darling daughter...Are you enjoying this?" Asked my mother.

"UmmUfmfu" was all I could mumble.

"That perfect baby...Now slide your tongue over the tip of that thick penis and feel the slit in the tip; if you feel it open up and get wider, I need you to stop immediately as it means your man is getting ready to cum." Said my mother.

I kept licking and sucking on Jack's erection and felt him getting harder in my mouth. I felt my nipples getting bigger and rounder under my bra and I had zero sensation in my tiny penis as if was fully limp in my panties under my petticoat.

"I'm close to cumming." Grunted Jack.

"Honey...Stop sucking now and take your mouth off his cock." Said my mother in a loud and direct voice.

I immediately did as she asked, but secretly wanted to continue. Jack's cock was sticking out straight and was rock hard and throbbing as I pulled back. Jack immediately grabbed my mother's hand and pulled her toward him as he pulled her panties down. My mother quickly said to me;

"Go to your room honey. I want Jack to finish inside me. You can listen to us fuck from your bedroom."

I quickly did as she asked and was laying on my back on my bed in my full lingerie outfit when I heard my mother in her bedroom saying;

"Oh my God Jack...I never felt you so hard and so big! Fuck me baby...Fuck me deep!"

I heard the two of them grunting together and Jack gasped;

"I'm cumming baby!..I'm really cumming!"

My mother began to gasp and I thought she too was having an orgasm as Jack breathed heavily and was no doubt shooting his spunk deep inside my mother. This went on for at least a couple of minutes as the two of them climaxed together. When things quieted down I heard my mother roll off of the top of Jack and the two of them were in bed together catching their breath with my mother still wearing her bra. It was a few minutes later I heard Jack saying to my mother;

"You know babe, I have a multi-millionaire friend who would pay you a lot of money for a girl like Linda."

"What do you mean? Sell my daughter to another man?" Asked my mom.

"I mean, he would pay you a large amount of money to have your daughter all to himself. He has told me many times how he is very attracted to girls like Linda."

"How much do you think he would pay?" Asked my mother.

"It could be several hundred thousand dollars. He's very rich and I'm sure would be very willing." Said Jack.

"That kind of money would solve all of my problems. And he would protect and take care of Linda?" Said my mom as she started thinking.

"He would worship Linda, and you would be sitting on a huge pile of cash. Do you want me to ask him?" Asked Jack.

"I'll need to confirm things with Linda, but I know she wants to live full time as a girl. Other than sucking on your cock tonight she is a complete virgin sexually." Smiled my mom.

"You could probably charge more for that." Interrupted Jack.

"I'm liking this idea...And I'm pretty sure I could get Linda to like it too...Okay, reach out to your friend in the morning and tell him you have found someone for him. I'll talk to Linda and tell her what we have planned." Said my mother.

My mother and Jack spent the night in her bed and I changed into a long nylon and lace nightgown with my panties on underneath and stayed in my room. In the morning I heard the sounds of my mother sucking on Jack's cock and his moaning as he ejaculated what I assume was a full load into her mouth. My mother made contented sounds as she swallowed Jack's semen and sperm.

When my mother and Jack were in the shower together I went into her bedroom and found a long nylon and lace robe that I put on over my nightgown and panties. I was at the breakfast table when my mother came into the kitchen and began to discuss her idea with me.

"Linda honey...Jack has told me of an idea that I think you will like and it will solve all of our financial difficulties."

"It sounds too good to be true...What do we have to do?" I asked.

"Well...it would involve a financial arraignment between me, you , and another man who would want you to live the rest of your life with him as a girl, and maybe even as his wife." Said my mother.

"Oh wow! I wasn't expecting you to say that at all!" Was my surprised response.

At that moment Jack came into the kitchen and my mother said to him;

"Baby, tell Linda about your friend."

"Oh, well, he's very rich and he has been talking to me about finding a "special" girl for several years. He is very handsome and in his mid-thirties and has a fascination with the feminization process. I know he would be interested in meeting Linda if I let him know about her."

"How about the four of us going out to dinner together on a date to see if Linda and your friend could hit it off? Is that something you would be willing to do Linda honey?" Asked my mom.

"It does sound exciting if you say he is handsome. You'd let him know how young I am and how much of a sexual virgin I am wouldn't you?" I replied.

"Of course honey. Jack...Why don't you set up a date for the four of us? I'll help Linda look as pretty and feminine as I know she can be and we'll hope there is a future for her with your friend." Said my mom.

"Okay. I'll do it and we'll see where things go from there." Replied Jack.

Part Two of this story tells about the beginnings of a new life.