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Second Encounter

"Monique and Jenny continue their adventure"

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Author's Notes

"Monique and Jenny are two mid-thirties crossdressers who met for the first time in the series “First Encounters”. <p> [ADVERT] </p>This is the story of their second meeting."

We have arranged our second encounter to be at a beach house in Duck, on the Outer Banks of North Carolina. You have made the arrangements and sent me the address, and I am to meet you there.

I am filled with anticipation as I pack my bags. I include my makeup, wig, sexy teddy, stockings, and my latest purchase, a 38D silicone breastplate complete with realistic nipples. I also pack a one-piece bathing suit and several sundresses and sandals.

I arrive at the address and am impressed by how secluded it is. Although it faces the ocean, it is several miles from the nearest dwelling and set back from the road several hundred feet. My heart leaps when I see your car in the drive.

As I climb the stairs I am trembling with excitement at seeing you once more. I knock on the door, and you open it and greet me with a warm smile. You are a picture of femininity, your makeup and wig are impeccable, and you are wearing a light summer dress, tan thigh-highs and sandals. Your nails and toenails are painted a bright red, complementing your ruby lips. We hug, and our lips meet in a familiar embrace, our tongues dancing with delight.

"Hello, Monique, it's so good to see you again!" you breathe, and I am nearly speechless with delight at seeing you.

"I've missed you so much," I respond.

We kiss again, and you say, "I've never kissed a man before."

"I won't be a man for long," I respond and we laugh together. I grab my bags and head for the bathroom to change.

"I have a big surprise for you when you come out," you tease. "I think you'll be very pleased," you say with a wink.

I am trembling with excitement as I strip out of my drab clothes. A whole weekend with you dressed is almost too much for me to think about. I begin by shaving everything from my eyebrows down, taking special care on my cock, balls, and ass. I shower and towel off, apply my makeup and wig and slip into my panties, adjusting them so my stiffening cock is peeking over the top.

I don my new breastplate and strap on a peekaboo bra, letting the nipples poke out through the front. I pull the stockings over my legs and slip into the sundress. As I admire myself in the mirror, I hear you talking to someone in the next room. My thoughts return to your comment about a surprise, and I tingle with excitement at what it could be.

I make my entrance and spin in front of you, letting my sundress rise to show off my stockings and panties. "My God, Monique, you have boobs!" you exclaim with delight.

"They're my surprise, I hope you like them," I say.

"I love them!" you respond and give the nipples a tweak. "So real looking, it makes me want to suck them right now," you squeal.

"Go ahead, be my guest," is my response. You lower your lips and take the right nipple into your mouth.

"So soft, they feel just like the real thing," you say.

"Well, they should, as much as I paid for them," I answer. "What about your surprise?" I ask, expectantly.

You turn to look at the bedroom door and say sweetly, "Oh Jill, you can come out now."

I turn my gaze toward the door and am stunned by what I see. The most gorgeous image of feminine beauty appears before me. She is tall, at least six feet, with long blonde hair flowing halfway down her back, piercing blue eyes, long slender legs, and the most perfect chest I have ever beheld. Her large breasts are encased in a light cotton sundress with a plunging neckline, and I see she is not wearing a bra. Her cleavage leaves nothing to the imagination and her perfect nipples are protruding invitingly. I can see the outline of her panties and garter belt through her dress material. Her legs are encased in tan lace stockings, and on her feet she is wearing summer sandals. I peek discreetly at her crotch, hoping to catch a glimpse of a bulge, but a smooth triangle is all I see.

"Monique, meet Jill," you say, and I reach out my hand to take hers.

"Hello, Monique," she breathes, "It's a pleasure to meet you. Jenny has told me all about you." I am struck dumb, unable to utter a single word, completely mesmerized by the image before me.

"What's the matter, cat got your tongue?" you tease.

"Hello, Jill," I stammer. "What a pleasant surprise," is all I can manage to get out.

"We met on a crossdresser chat forum," you explain. "When we discovered we lived in the same town, we became friends. We've been seeing each other for several months now, and when you and I decided to meet here, it was only natural to invite Jill to come along."

"I'm so glad you did," I respond and in the back of my mind I'm hanging on the words "crossdresser chat forum".

"Let's fix a bite to eat and get to know each other," you suggest.

"Great idea," I respond, "I've brought some cheese and wine."

"I'll make a salad," you respond.

"And I'll cut up some fruit," Jill chimes in.

We busy ourselves with preparing the food, and when it's ready, we take seats around the table out on the veranda. The ocean breeze feels wonderful on my stocking-covered legs, and we pour the wine and settle in to eat.

"Tell me about yourself, Jill," I ask inquisitively.

"I'd be glad to," she responds. "I've always been a woman on the inside, but for the first eighteen years of my life, I was a boy." I am intrigued and fascinated by this response.

"Please explain," I say.

"Well, as far back as I can remember, I knew that I was born into the wrong body. I was a boy, with all the boy parts, but in my mind, I was a girl trying to get out. I started wearing my sister's panties and bras at sixteen. Fortunately for me, my parents were very understanding of my situation, and my mother started taking me shopping for my own clothes. We moved across the country and when I enrolled in my new school, I became Jill, and have lived as a girl ever since."

"That's fascinating!" I exclaim. "I've never met a transsexual person before. How did you get your womanly figure?"

"Well, I started hormone therapy when I turned eighteen, and have been on HRT ever since."

"And your...?"

"My boobs? I've been undergoing a series of breast enhancement surgeries for several years, and I'm about where I want to be with them," she replies.

"Well, they certainly are impressive," I exclaim.

"Thank you, and so are yours," she replies.

I'm apprehensive to ask the next question, but I have to know the answer. "What about your..." my voice trails off.

"My cock?" she asks. "My cock is still very much a part of me, and is still quite functional," she replies.

"Yes, a very large part of her," you chime in, and the two of you look at each other and giggle.

"So how big is it?" I blurt out.

"Let's just say you'll be pleasantly surprised at the size of it," you say, and give Jill a sly wink.

My head begins to spin. This is beyond my wildest dreams. A weekend at a beachfront cottage, dressed as a woman, with you and a beautiful transsexual woman! I'm overwhelmed at the possibilities! This must be some sort of fantasy is all I can think.

"Let's clean up and get comfortable," Jill suggests.

We quickly clear the dishes and retreat to the living room. Jill stands in front of the couch and announces, "Here's how I get comfy." She raises the hem of her skirt, slips off her panties, and spreads her legs slightly. I catch a quick glimpse of her flaccid cock as it swings from between her legs. It is truly massive, and while still soft, must be at least seven inches long. I can see she is uncut, and her large knob is sheathed in a huge hood.

She reaches up and frees her balls from their nesting tuck, and says, "There, that's much better. Why don't you ladies do the same?" We both drop our panties and our stiffening cocks look like tent poles beneath our dresses.

Jill takes a seat in the middle of the couch, spreads out her arms across the back and says, "Won't you two join me?" We quickly take seats on either side of her, me to the left and you to the right. She nestles us close to her and purrs, "Let's get to know each other."

She turns her head in your direction and your lips lock passionately. I bend down and free her left breast from her dress and begin to lightly lick her nipple. I suck in as much of her tit as I can and run my tongue over her soft flesh. My hand instinctively goes to her crotch, and I gasp at my first touch of her cock. Like a sleeping giant awakening, it is stirring and rising. Its girth is so huge I can barely wrap my hand around it.

You break your lip-lock with Jill and I tilt my head upward. She responds by turning my way and opening her lips slightly. Our tongues meet and we exchange a long passionate kiss. Your mouth goes to her right breast and I feel your hand joining mine on her cock. It is stiffening and twitching in our grasp and we begin to slowly jack it. Now both sucking a tit, we increase our rhythm on her cock, and she responds with a low moan.

"That's nice, girls, suck my tits and jack my cock," she mutters. We continue for several minutes as her cock reaches a full twelve inches.

Our lips leave her nipples and meet at her chest. We kiss deeply and I hear you whisper, "Do you want to go down?"

"Do I ever!" is my response. We kiss our way down her stomach and I get my first good look at her monster cock. It is truly a thing of beauty, a full foot long, with thick veins glistening with precum. I peel back her hood and behold her huge knob.

"Oh Jill, your cock is so beautiful!" I exclaim.

"Thank you, Monique," she pants, "I've been told that before."

We begin by licking her balls, each of us taking one in our mouths, gently rolling them around and kissing them. We then move up her shaft, you licking on one side and me on the other. We meet at her huge knob and exchange a passionate kiss, then return to licking and sucking her. I stretch my mouth over her head, my lips leaving traces of red lipstick on it. It fills my mouth, and I am consumed with a desire to take it down my throat.

"Has anyone ever been able to swallow your cock?" I ask Jill.

"Several girls have tried, but nobody has ever taken it all," she replies.

"I'd love to be the first," I say, "I've been practicing deep throating my ten-inch dildo and can get it most of the way down," I say hopefully.

"OK, you can try, but we'll have to move to the bed to get in position," she replies.

We quickly move to the bed and I lie on my back, my head hanging over the side and my cock pointing at the ceiling.

"I'll take care of this end," you say as you kneel between my wide-spread legs.

"I've got something to help you, Monique," Jill says as she reaches into her bag and pulls out an aerosol bottle. "This is antiseptic throat spray," she explains, "It will numb your throat and stifle your gag reflex."

I spray a shot into my throat and feel its numbing effect immediately. I lean my head over the side of the bed and lick my lips. Jill's massive cock is looming before my face and I am wild with anticipation.

"Open wide, here I come," Jill says and I willingly obey.


To be continued...

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