-3-
Before beginning my story about what happened to me the week before Christmas, I should explain what had happened during the past few months. Early in my senior year of high school, I had met a gorgeous girl named Bethany who became my girlfriend. On the day of our four month anniversary, we had sex for the first time.
What I didn't expect, however, was that my girlfriend was actually a transsexual or a "shemale." She had the face, body, and breasts of a woman, but she had male genitals. I was surprised at first, but was soon overcome by my desire for her. After giving her a blowjob, we had anal intercourse ending in the most phenomenal orgasms that either of us had ever had. Our love for one another was stronger than ever. After the sex, we went right to sleep, but the next morning I leaned about Bethany's true past.
I woke up the morning after our first time together. It was dark and I reached out to find Bethany, eager to hold her, but she wasn't in the bed with me. Somewhat alarmed, I switched on the light. It was almost noon. I got out of bed, still naked, and put on a pair of sweatpants before going downstairs. My parents were gone for the weekend, so we had the place to ourselves. Once I stepped out of my room, I heard the sound of bacon sizzling downstairs. The smell hit my nose and I grinned stupidly. Bethany knew how much I loved bacon. I ran downstairs to find her there, dressed in a black negligee which she had brought from home, cooking at the stove. "Good morning sleepy," she said.
"Good morning beautiful," I replied. I stood behind her and wrapped my arms around her waist. I kissed her neck several times. "How long have you been up?"
"About an hour," she replied. "Your snoring woke me up."
"Ha," I said, poking her in the ribs. She giggled.
"Sit down," she said. "Let's eat." She served the bacon on to two plates with eggs and set them down on the table. I sat down as Bethany poured me orange juice before sitting down herself.
"This looks delicious," I said. "Thanks honey." She smiled as we began to eat. Half way through the meal I said, "I have to know Beth. I mean, I accept who you are and I love you for who you are, but I need to know how you became the way you are."
"Like any other transsexual," she said. "I was about eleven years old and I knew that there was something different about me. I was a boy. My name was Brandon, but I felt like a girl on the inside. I used to wait until my mom was out of the house and dress up in her clothing, strut around, pretend to be a real girl. One day, when I was 15, she caught me. I broke down crying and told her that I wasn't supposed to be a boy. She took me to see a man named Dr. Laine, who was a gender therapy specialist. I met with him for about a year and I was diagnosed with gender dysphoria, which is the medical term for transsexualism. I spent a year out of school, taking hormones and living as a girl. My breasts grew. My hips got wider. My hair and skin and voice became softer. Eventually, I became the girl you see before you. I enrolled in our current high school and the rest is history."
"And I couldn't have asked for a better one," I said. I squeezed her hand. "I love you Bethany."
-4-
A week before Christmas, I was sitting alone in Bethany's room. She had called me from the dentist's office where she worked part-time and told me to go to her house and wait for her to get home. She told me that her mother wouldn't be home so I could just walk in. Bethany's father didn't live with them. "My father is gone," she said to me once. I assumed he had run off with another woman.
Life was good, but strange. I didn't consider myself gay, but I just couldn't seem to get enough of Bethany's dick. I loved sucking it and jerking her off. I was virtually addicted to my girlfriend's cum. Still, my life was perfect and I didn't want one thing to change. That's what I was thinking about as I waited in Bethany's room.
I was looking at the pictures on her nightstand. There was one of Bethany and me in New York City, where we took a day trip in November to see a Broadway show. In the picture, I had my arm around her and we're both smiling happily into the camera. I admired another picture which was of Bethany's mother. Mrs. Mayer was a beautiful woman, almost as beautiful as her daughter. She was in her late forties with her daughter's pretty face and spectacular breasts. Mrs. Mayer was a bit heavier and a bit taller than her daughter, but still gorgeous. Mrs. Mayer had liked me instantly when we first met. Sometimes, however, I couldn't help but wonder if Bethany had told her about our sexual experiences. It's not as if Bethany's transsexuality was a secret to her mother, but it still made me feel strange.
I was beginning to get bored. Bethany was obviously late. Suddenly, I got a strange idea. I walked over to the dresser and opened the top drawer where Bethany kept her underwear. There were all kinds in all colors - pink, purple, white, sky blue, and maroon. Some were lace, some were satin or silk, and some were plain cotton. She also had a few teddies and thongs.
I pulled down the shade and checked to see if there was a car in the driveway. Bethany's room was positioned well so I could see headlights if anyone came home.
My heart was pounding in my chest, but I was very aroused by all of Bethany's delicate undergarments. I could understand why she had such a collection. She had lived as a boy for 16 years and she was finally taking the opportunity to be a sexy girl in sexy lingerie. Who could blame her? I quickly stripped off my clothes. My cock was rock hard and stood at full attention. I took out a pair of pink panties from Victoria's Secret and sniffed them. They smelled as sweet as Bethany, but with traces of her delicious cum. I stepped in them and wriggled until the panties were covering my crotch. They were tight, but the fabric felt wonderful against my skin. I searched for the matching bra and put it on as well. I felt so sexy as I slid the straps over my shoulders.
I posed in front of the mirror, imagining my hot girlfriend in this underwear. I admired how my ass looked in the sexy panties. I caressed myself and cooed softly, pretending I was a shemale like Bethany. Suddenly, the door opened. I wanted to hide, but I was standing out in the open! I could only imagine how Bethany would react to this. I was petrified.
But it wasn't Bethany at all. Mrs. Meyer opened the door and walked in, not expecting anyone to be in there. "Eric!" she cried. "Eric, what are you doing?" All I could do was look down in shame. I felt like I was going to cry from embarrassment.
"I'm sorry," I said. "I just saw Beth's underwear and I wanted to try it on for some reason. Please don't tell her. I promise I'll never do it again."
"I won't tell her," said Mrs. Meyer, her tone softening. "I understand that boys need to wear girly clothes sometimes. Believe me, I've been through all this before. Bethany told me that you had sex, so you know her little secret." I nodded slightly. "I was so shocked when I caught my own son dressed as a girl. I don't think anything can beat that."
"I hate to be rude," I said. "But I need to put on my normal clothes again . . ." For the first time since she caught me, I took a look at Mrs. Meyer.
She looked beautiful as always in a black skirt with black stockings and a white blouse. She was wearing her honey-blonde hair up. It was ridiculous for me to be checking her out, considering I was practically naked, wearing only her daughter's panties and bra.
She ignored me. "I can tell what my daughter sees in you," she said, closing the door behind her. "You're very cute. I think it's very sweet of you to love Bethany for who she really is, not just as a sexual object. Most guys wouldn't have done what you did. I know she loves you very much."
Mrs. Meyer pulled the clip out of her hair and it came tumbling down. "Of course, I know one thing she doesn't."
"What's that?" I asked.
"I know how good you look in lingerie." She smiled seductively as she walked over. Mrs. Meyer put her hands on my waist and kissed me. I felt wrong for doing it, but I couldn't resist. Seeing Beth's hot mother and feeling Beth's hot underwear against my cock, there was nothing I could do except kiss Mrs. Meyer back.
As we kissed, she unbuttoned her blouse, exposing her black satin bra underneath. Her breasts were spectacular. I begin to kiss them through the bra. She pushed my face deep into her breasts where I was nearly smothered by the warm flesh. Mrs. Meyer removed her her blouse, giving me free access to her boobs. I almost forgot that I was still wearing girls underwear. "You've been naughty," she said. "You've been dressing up in my Bethany's pretty underclothes. That's not what boys are supposed to do. I'm going to have to spank you. Bend over."
I had never been into discipline, but I couldn't resist the big tittied vixen. I bent over, putting my hands on Bethany's bed. I felt the palm of Mrs. Meyer's hand slap loudly against my silk-covered butt. I let out a small moan. She slapped me again. The pain felt delicious.
"I don't think you've learned your lesson yet. Sit down." I sat down on the bed as Mrs. Meyer began to remove her skirt. She stood in front of me, tall and proud, in matching black bra and panties with a garter belt to hold up the black stockings. She was a dark mistress with her sissy boy dressed in pink frilly panties. "Now how do I teach a little boy who can't keep in his own clothes?"
Honestly, I shouldn't been surprised at what happened next. Mrs. Meyer pulled aside the front of her panties and out popped her dick. I finally understood what Bethany had meant when she said her father was "gone." I gazed in wonder at the cock, which was even bigger than Bethany's. "I know you love girls' dicks," said Mrs. Meyer, "so that's what you're going to get. Bend over."
I did as I was told, slightly afraid of being penetrated by the woman's huge dick. I wasn't sure my asshole could handle it. Her long, slender fingers wrapped around the elastic waist of the panties I was wearing and pulled them down to my knees. "Spread 'em," she ordered.
I reached behind me and spread my butt cheeks wide, exposing my asshole. Mrs. Meyer put the tip of her cock against my anus and began to smear it with pre-cum. I tried to relax my sphincter as I felt her dick begin to enter me. It was a strange mix of pleasure and pain, but it felt amazingly good. I understood why Bethany had turned from a sweet virgin to a butt-slut overnight. This was an incredible feeling! My butt muscles flexed as I tried to take all of her ten inches into me.
By the time she was all the way in, I was practically screaming in delight. I began to stroke my own cock, hoping I would get a chance to probe Mrs. Meyer's "pussy" before the night was over. "Go ahead and jerk yourself off," said Mrs. Meyer. "I love watching boys cum." She put her hands on my hips and pulled me towards her as she fucked me. I groaned and moaned as she reamed my tender butt. I knew I would have to teach Bethany to fuck me too.
"I'm no where near cumming, baby," she said. "I'm going to enjoy this for as long as I can."
"Thank God," I said, turning to smile at her. She winked back. "My daughter picked a good one."
-5- Speak of the devil. At that moment, Bethany burst into the room. "Mom!" she yelled. "Eric! How could you do this without me?"
Mrs. Meyers and I laughed as she kept fucking me. Bethany walked over to her mother. "Hi Mom," she said. Bethany and her mother kissed deeply, their tongues moving in and out of one another's mouths. Bethany squeezed her mother's breast and pinched her nipple as they made out. Apparently, the Meyers ladies had more than one secret.
"How was work?" said Mrs. Meyers.
"Good. Say, what is Eric doing in my underwear?"
"I told him to wear them," said Mrs. Meyers. "You know I love transvestites." The two of them laughed.
Bethany looked down at me. "The only reason I don't consider this cheating," she said to me, "is because I know how good it feels to be fucked by my mom. Her dick feels SO good, doesn't it?" I nodded. "Well, Beth needs some attention too."
Bethany climbed on to the bed and crawled in front of me on all fours. Her cute butt was directly in front of my face. She pulled up her plaid skirt and pulled down her panties. "Eat my pussy," she said. I had never given her a rimjob before, but I loved the idea. I used my hands to spread her buttcheeks, exposing her sweet asshole. I licked the rim of her asshole until it was shiny with my saliva. Then, I worked my tongue in, tasting the foul delights. Bethany moaned. I licked my finger and shoved it in. I licked as I fingered her. She was in Heaven. I moved from her asshole to her balls and began to kiss them lovingly. I ran my tongue from her scrotum all the way up her asscrack then I began to plant wet kisses on her asscheeks.
At that moment, Mrs. Meyer pulled out of me. She hadn't blown her load, I knew. "What's wrong?" I said.
"Nothing," said Mrs. Meyers. "Go sit down in the chair." She pointed to the chair on the other side of the room. I removed my panties completely, but still left the bra on. I sat down in the chair. "I'll show you what us girls like to do for fun."
Bethany and Mrs. Meyers sat down next to one another on the bed, leaning against the headboard. Bethany pulled up her skirt, revealing her own beautiful dick. Then, she reached over and grabbed her mother's hard cock. Mrs. Meyer did the same for her daughter. The two women closed their eyes and began to jerk each other off. Obviously, they had lots of practice with one another. "Oh yes . . . Mom . . . harder," said Bethany blissfully. Mrs. Meyer began to jerk harder.
Instinctively, mother and daughter leaned in together and french kissed. At that moment, streams of hot white cum shot out of their dicks, covering one another. They grabbed each other's breasts, smearing their jizz all around.
I walked over to the bed and stood next to them, masturbating. The two women smiled at me as I shot my cum on their faces. Afterwards, I sat down next to them and the three of us - our happy little family - sat sweating and panting in our own semen. My only thought was the need to feel my girlfriend's dick inside me. I closed my eyes. It would happen soon enough.
To be continued . . .