-6-
February 16th was my birthday and I was eagerly awaiting spending the day (and night) with my girlfriend, Bethany. I had met Bethany six months earlier, when she was just a new student in my high school. I had fallen in love with her at first sight and becoming her boyfriend became my top priority. Not long after, Bethany and I were a couple. We had a great relationship in all matters except sex. Bethany was reluctant to give herself to me and never provided a clear reason why. On the night of our four-month anniversary, I got my answer.
After having an earth-shaking orgasm from one of Bethany's exquisite blowjobs, I questioned her about why she was so reluctant to have sex. To my surprise, she began to cry. She put my hand on her crotch and I felt what was unmistakably a penis. Bethany stripped before me, showing me her perfect body and I was overwhelmed by desire for her. We made love passionately and I got my first taste of cock, which I absolutely loved. One that day, our relationship became even stronger.
It wasn't long before things took a strange turn. I was in Bethany's room, waiting for her to come home, thinking I was alone in the house. To amuse myself, I tried on Bethany's underwear only to find that it really turned me on. At that moment, Bethany's mother Caroline Meyer, walked in. Apparently, seeing me in panties and a bra turned her on as well. She stripped down to her lingerie and revealed that transsexualism ran in the family. Mrs. Meyer filled me with her wonderful cock. It was my first time being on the receiving end of butt sex, but it was absolutely incredible.
It became even more incredible when Bethany walked in. As it turned out, mother and daughter had been sexually involved with one another for quite some time. As Mrs. Meyer continued to fuck me, I ate out Bethany's asshole for the first time. For the grand finale, the three of us blew our loads together.
-7-
On the night of my birthday, Bethany and I were together in her room. Her mother was asleep so we have plenty of privacy (not that she would have cared if she heard Bethany and me having sex.) For my birthday, my girlfriend had given me a few CD's that I wanted and an expensive sweater from the GAP. I used to be a T-shirt and jeans kind of guy, but it had changed as I dated Bethany. She loved to dress me up in preppy clothes. I didn't resist. (Any single guy reading this will say I'm whipped, but any guy with a girlfriend knows what I'm talking about.)
"I have a special present for you," said Bethany. "I didn't want to give it to you in front of your friends." My cock twitched. I assumed she meant sex. She gave my dick a playful squeeze through my pants. "Not that," she said, "a real present." Bethany bent over, giving me a nice view of her tight butt. I never got tired of staring at it. I could also tell she was wearing a tiny thong underneath her jeans.
"What is it? What is it? What is it?" I asked. She pulled out a flat box wrapped in pink wrapping paper with roses on it.
She handed me the box and kissed me on the cheek. "Happy birthday, honey."
I put the box to my ear and shook it. "It's not a new car," I said. Bethany stuck out her tongue. I chuckled and set the box down on my lap. I tore through the paper like a child at Christmas. I pulled off the paper as eagerly as I pulled down Bethany's panties when I gave her a blowjob.
All the paper was gone, revealing a plain white box. I pulled off the top and set it aside. Inside the box, lying on a bed of white tissue paper, was a green lace teddy from Victoria's Secret. "I know you've been crossdressing," she said, putting her arm around my waist. I blushed. I had my first crossdressing experience wearing Bethany's underwear late last year. Since then, I had amassed a small collection of ladies' underwear from eBay. There was nothing fancy and nothing nearly as sexy as this teddy.
"It's perfect," I said. I leaned over and deeply kissed my girlfriend, groping at her body. I slid my hands up her shirt to fondle her breasts through her bra. Their sheer enormity never failed to amaze me. They were so big and round yet perky, soft yet firm. "Take off your pants," I whispered. Bethany stood up next to the bed and pulled her pants down to her ankles, showing me her perfectly smooth, muscular legs. She was wearing a tiny blue thong, which was too small to hide the bulge. The tip of her cock was peeking out from the side. I reached out and slid my fingers under the elastic. Slowly, almost painfully slowly, I pulled the thong down. I could only look, mesmerized, at Bethany's beautiful cock dangling in front of my face.
I kissed the limp shaft as I removed my own pants. Bethany ran her fingers through my hair as I ran my tongue along her wonderful dick. She put her hands on my shoulders and gently pushed me on to the bed. Then, she walked to the other side of the mattress and crawled across it until we were in a 69 position. I looked up to see her large, baby-smooth balls hanging over my eyes. The tip of her penis brushed against my lips.
I began to lick the veiny back of her shaft as I worked my way up to her scrotum. I opened my mouth wide and let her testicles fill my mouth. I began to gently squeeze her balls with my lips as my tongue danced across the wrinkly skin, just as her sensual mouth took in my own member. The pleasure was exquisite, feeling her tongue on my cock while tasting her warm dick flesh in my mouth. For a moment, I thanked God that my girlfriend was a shemale.
I then focused my attention on her penis, suckling at it lovingly, as she did the same to me. Hers was now rock hard and throbbing, aching to fill my mouth with her jizz. As I sucked, I put my finger in my mouth and covered it with saliva for lubrication. I spread her ass cheeks with the non-lubricated hand and inserted my finger into her tight butt hole. The muscles clenched as her anus swallowed my finger.
A faint moan escaped her cock filled mouth. She was beginning to face fuck me now, not bothering to be stimulated by my tongue or lips. I knew this meant she was close to cumming. I increased my speed as well. There was nothing more intense than when Bethany and I had our orgasms together.
A second later, the sublime pleasure washed over my crotch as I ejaculated. At that moment, a deluge of Bethany's sperm flooded my mouth. I swallowed it down quickly and then sucked hard on the tip of her penis to squeeze out every last drop of her delicious cum. I could feel her throat constricting around my penis as she swallowed my jizz as well.
Once we had recuperated, Bethany and I snuggled together, still only wearing t-shirts. "Happy birthday, baby," she said. I smiled and hugged her tightly, our cocks rubbing together.
-8-
A few days later, Bethany called me on the phone, fuming mad. "You'll never believe what happened!" she said. "Justin Schubert just tried to ask me out! He knows I'm already going out with you, but I decided to refresh his memory, and he says, 'Eric's not enough of a man to satisfy you.' I just walked away after he said that. Can you believe it?"
"Sort of," I said. "Justin Schubert has hated me since we were 11 years old. Of course, I can't blame any guy for being attracted to you."
"Well, thanks," she said, "but it still annoys me. What a creep."
"Yup."
Bethany was silent for a moment. I knew she was thinking. "I have an idea she said. I know how we can get back at him."
"How?" I asked.
Later that night . . .
"This is never going to work," I said. Bethany and I were in my bathroom. I was sitting on the toilet, naked, as Bethany applied lipstick, mascara, blush, and eye shadow to my face.
"Of course it will," she said. "You'd be amazed how much make-up and a wig can change a person. Besides, he'll never expect to see you dressed up. You'll catch him completely off guard."
"I'm only doing this because I love you," I said.
She smiled and kissed me on the forehead. "I know," she said. "OK, all done." Bethany stepped away from me. "Now let's get you dressed." First, Bethany handed me the green lace teddy she had bought me for my birthday. I stepped into it and slowly slid the garment up my body. The lace felt painfully sweet against my cock. The g-string back wedged itself in my buttcrack. The shoulder straps went nicely over my arms. It was a perfect fit. I took a moment to admire myself in the mirror. I could see Bethany smiling in her reflection.
"I look terrible, don't I?" I said.
"No!" she said. "That's why I'm smiling. I didn't expect you to look so, well, hot!" I chuckled. Bethany handed me two rubber fake breasts to stuff into the cups of the teddy. "I used to use these before the hormones kicked in," she said. I inserted them and was amazed at how well they blended with my skin. It actually looked like I had tits almost as big as Bethany's. I was really beginning to enjoy my womanhood. Next, I put on a short black skirt with matching block stockings and a tight maroon top. It suddenly occurred to me that I was wearing the same outfit that Bethany had worn on the first day I saw her in the hallway at school.
I grabbed the last accessory, the wig, and placed it on my head. I straightened my fake hair and looked at myself. I really looked like a woman and I looked absolutely nothing like myself. I was taller than Bethany and a bit thinner, with small breasts, but I still looked damn fine!
"You look great Erica," she said, linking arms with me. "We're supposed to meet Justin at the mall at 7:30, we'd better hurry. This is going to be so much fun!"
-9-
Bethany and I walked into the food court in the mall. I was trying to balance myself in my black heels. Although I was nervous and awkward, I felt incredibly sexy. The girly clothing clung to my body like wet silk and every move was an intoxicating step into the world of femininity. I was worried my cock would bulge through my skirt. "There he is," said Bethany. Sure enough, there was Justin Schubert, sitting in front of McDonalds, wearing his trademark baggy khakis and crooked visor. He looked over and Bethany waved.
Justin strutted over. "So," he said to Bethany, "what made you change your mind?"
"I thought about what you said," replied Bethany. "You're so much more of a man than Eric." I almost burst out laughing. At that moment, it was true. Justin looked over at me, checking out my breasts and legs. He barely even looked at my face. There was no recognition in his eyes. "This is my older sister, Erica," said Bethany. I was positive the Erica thing would give me away, but apparently Justin was too stupid to figure that out either.
"So what do you ladies want to do?" said Justin, trying to be smooth.
"Is anyone home at your place?" Bethany asked. Justin shook his head, smiling broadly. Bethany flashed him her most seductive smile. "Well," she said, "why don't we go 'hang out' there for a bit?"
Soon, we were at Justin's house, hanging out in his furnished basement. Bethany and I were sitting on the couch as Justin brought us drinks. I was very careful to keep my legs together so he couldn't peek up my skirt. I watched Bethany and imitated her movements to look more feminine. Justin still hadn't caught on to my little secret. "I never knew you had a sister, Bethany," said Justin, making small talk.
"Oh yes," said Bethany, putting her hand high on my thigh. "We're very close." Justin's eyes fixed on my thigh.
"How close?" asked Justin.
Bethany smiled. She put her hand behind my neck and pulled my face closer to hers. Our lips connected and our tongues began to mingle. It was a strange sensation to kiss while wearing lipstick, but very pleasant. I felt the same indescribable joy I felt when kissing her, the woman I truly loved. But, I could never imagine what Justin was thinking, watching two gorgeous "sisters" making out like horny sluts. Bethany fondled my fake breasts. Out of the corner of my eye, I saw Justin watching us intently with his hand deep in his pocket. I realized he was fondling his dick, which must have been incredibly hard.
"Come sit between us," said Bethany. Without a moment's hesitation, Justin came and squeezed in between Bethany and I. "Erica," she said, "why don't you do the honors?" I winked at Justin as I began to reach across his crotch. I unfastened the button and unzipped his fly. I pulled down the elastic waist of his boxers and his seven-inch cock immediately sprang up. It was the first time I had ever sucked a man's penis, but I went right to it.
I lowered my head down and took all seven inches of his shaft in my mouth for starters. I'd had all my oral sex practice on Bethany and she was actually bigger than Justin, so he was easy for me. I worked on him the same way I worked on Bethany, massaging his shaft with my tongue and applying the proper amount of saliva for lubrication. He pushed my head down, something Bethany never did, but I didn't object.
I looked up just in time to see Bethany lowering herself down as well. Together, my girlfriend and I licked Justin's shaft up and down. His hands were in tight fists and his jaw was clenched hard. I knew he had never experienced a blowjob like this before. Our tongues chased each other around the tip of his cock to the sensitive area behind the head. As Bethany began to suck, I began to lick at his balls. I was used to Bethany's bald scrotum and was almost surprised to find that Justin had hair on his, but I didn't complain. I took his big sack in my mouth and drenched it with my spit, slurping audibly.
"I'm gonna cum . . ." he said softly. At that moment, Bethany and I stopped sucking. "What are you doing?" he asked.
"Wouldn't you rather come inside one of us?" Bethany asked.
Justin's face brightened. "Fuck yeah!" he said.
"Well, who's it gonna be?" she asked. "Me or Erica? Take your pick."
He thought for a moment. "Erica," he answered.
"Alright," said Bethany. "But there's two stipulations. First . . ." Bethany removed a black, silk scarf from her purse and wrapped it around Justin's eyes, blindfolding him. "You have to be blindfolded," she said.
"What's the second stipulation?" he asked.
Bethany winked at me. "You have to fuck Erica . . . in the ass. That's how she likes it."
"Really?" he said. "Awesome! But, Bethany, can I fuck your pussy after?"
She nearly burst out laughing. "We'll see," she replied. "Take off your pants." Justin did as instructed, and then Bethany guided him to a kneeling position on the floor. I got on my hands and knees in front of him. I lifted up my skirt and pulled the g-string back of the teddy aside. My cock was about to burst. I grabbed my balls and pulled them forward a bit so that Justin would not notice his scrotum flapping against mine.
Bethany spit into her palm and rubbed it along Justin's dick until it was wet and slippery. Then, she guided the tip between my ass cheeks until it was pressing against my anus, poised to enter. He began to push, Bethany's gentle hand guiding him all the way in. Soon, I could feel his bristly pubic hairs against my ass. I let out a soft, girly moan. He began to pump in and out, feeling my insides with the ecstasy one can only achieve through a sublime buttfucking.
Bethany removed her dress and took off her bra. I noticed that she wasn't even wearing underwear. She sat down on my back, facing Justin, her cock stretched out before her. She took Justin's hands off my hips and placed them on her tits. He began to squeeze and kneed her breasts as he fucked me even harder. I was about to reach orgasm. I could feel it coming. Justin began to suck on Bethany's nipples as he reached out to finger her "pussy." She was quick, though. She caught his hand while it was an inch away from her dick and placed it back on her breast.
"I'm going to cum . . ." said Justin again. "Shoot it in her ass," said Bethany. A second later, warmth spread through me as Justin pumped his jizz into my asshole. As soon as I felt it, I grabbed my own cock and jacked it furiously until spilling a load all over Justin's carpet. He pulled out slowly and fell back on the floor, trying to recover from the most intense orgasm of his life.
Bethany and I took advantage of his momentary paralysis. She found her dress and quickly put it back on. I straightened my skirt. Just as we had finished covering our cocks, Justin removed his blindfold. "Erica," he said, "that was incredible." I smiled and blushed. "Thank you too Bethany. Next time, you'll have to let me fuck you."
She smiled. "I don't think so Justin. I have a boyfriend." He looked at me questioningly and I shrugged. Bethany and I giggled as we left Justin on the floor, wondering what the hell had just happened.
As we walked out the door, we heard him say, "What's this cum stain on the carpet?" and we were gone.
-10-
So ends the story of my early sexual encounters with my transsexual girlfriend, Bethany. But, two summers later, the real story of my life began.
It was July. Bethany and I were both home from college on vacation and we had decided to go for a walk in the woods. We strolled along casually, hand-in-hand. Crickets chirped far away in the swamps. Birds overhead sang. The sunlight dappled down through the leaves. I couldn't have pictured a more beautiful landscape. I couldn't have asked to be with a more beautiful woman.
"These past three years have been the greatest I could ever hope for," I said. Bethany looked up at me and smiled. "I'm not just talking about sex, although I certainly LOVE that as well. I mean, every moment I'm with you, I seem to fall deeper in love. Just kissing you, hearing your voice, or holding your hand fills me with this incredible sense of peace and happiness. Even the fights we've had have made me love you more."
"You're so sweet. I feel the same way about you," she said.
"But there's one thing that scares me," I said. "I'm terrified of having to live the rest of my life without you. I couldn't stand that." She looked at me quizzically. I stopped, turned to face her, and took both of her hands in mine. "So, I need to make sure that doesn't happen." I got down on one knee in front of her. I could see she was about to cry once she realized what I was doing. "Bethany, will you marry me?"
"Yes!" she cried. I stood up quickly and she jumped into my arms. We hugged, kissed, cried, and lived happily ever after.