Serving with Distinction: Chapter 5: Losing my Virginity All Over Again

I see my vision grow brighter and brighter as a white void surrounds us. Out of nowhere a bed and hanging linen comes to view out of the corner of my eye. White silk sheets and cashmere cover the huge bed. I’m not sure if we moved, or everything around us did, but I feel like we are nowhere near the pond. We both fall into the bed brought before us. It’s cushion is silent, but it caresses us like nothing mortal.

Face to face, Luna and I gaze into each other between moments of heated kissing. As a man, I enjoyed the tender moments and foreplay but this was something else, something I’ve never felt before.

She looks at me with omnipotence, like she has always known me as her lover. Hair falls in front of my face, adding a comic jarring to our passionate moment. She brushes it out of the way and we smile together.

“You’re gonna get used to your new body in time my darling,” Luna says reassuring. “I’ll teach you some of what you need to know as a woman.”
Her left hand on my face begins to wander as she resumes kissing me deeply and more intensely. I feel her fingers gently trace circles on my nipples, caressing the flesh I now own.


I let out a moan, shocked for second at the noise I utter, but quickly Luna brings my attention to her.

She kisses me like no woman has ever kissed me before. Her tongue is in control but the movement of her lips in tandem makes the experience wonderful on its own. I feel her hand wander again further down my torso. I try and brace for the sensations I expect to come next. It’s fruitless.


Her index finger begins to trace the hood covering my clit while her other fingers begin to rub my labia. The sensation of her rubbing my pussy, tells me I’m getting wet. The sensation feels so foreign to me. I always had a hard-on tell me how I felt as a man. Now as a woman, a deeper sensation builds inside me.


I rub my legs together tight, trapping Luna’s hands for a moment as I try and get wits together. But with a hidden strength she adjusts and mounts on top of me, never breaking her contact with my lips. Her body lies even to mine, our nipples are touching. She gently rocks her chest against mine, giving me another sensation I never knew before.


“A woman’s body is delicate and sensitive, but a werewoman’s body transcends that my child,” Luna says in the brief pause of our love making. “You will find it will not take much to turn you on. Learning to master your inner voice and desires is the first challenge all of our kind face.”

“How can I control myself, I feel like I’m about to explode,” I exclaim.

“Like with any art or craft…practice,” Luna says with a devilish grin.

Luna immediately repositions herself and begins to knead my breasts with her hands as she licks between my cleavage.


I move my hand to my mouth to cover my moans.

“No need to hide your joy and pleasure honey, we are alone and far away from anyone else,” Luna reassures me.

She traces circles on my nipples with her tongue, using her hands to stimulate the soft mounds I now admire. They feel bigger I think to myself. It’s a weird feeling seeing her fondle me like this, considering I was once in her place. Then again, being caressed and sexed by the spirit of your ancestor is something I never considered as a possibility of experiencing.

She squeezes my breasts together and takes both nipples into her mouth.

“OOOOOOOOOOOAAAHHHHHHHHHHH!!!!!!!!!!!!” I scream as my hips buck.

Her tongue whips my nipples while her lips make a seal around areolae. Her method reminds me of how I liked to fondle my lover’s breasts. I was always a boob man as they say. Well now I’m glad I got my own. In a split second the pleasure becomes too much and my orgasm takes off.


My back arches as a shudder in pleasure my body never knew. My eyes roll back and my moans fill the void. Like tasting dessert for the first time, I think to myself.

“AHHHHHHHHHHH,” I come down slowly from the orgasmic high.

Luna gets off me and I sit up to see a small pool of my cum on white silk sheets.

“I’ve only just started, you might want to hold on tight,” Luna says as she brings her face to my pussy.

I fall on my back and wait for the next wave of euphoria. I can feel her taking a moment of suspense as her warm breath dances across my skin, teasing me.


I moan louder as a she laps my juices with her wonderful tongue. Each movement, each point of contact her mouth makes sends a fire, a lightning bolt, a force a nature to my brain. As a man, blow jobs felt wonderful and intimate. Luna leaves all those feelings behind with each flick of her tongue. I feel intimidated by her abilities, but my fiery side takes over and I grab her hair in a vain attempt to brace for what she is delivering.


Her tongue makes all sorts of patterns, figure 8’s, up, down, side to side. I can’t keep track of all her actions, the pleasure begins to crowd any other sensation down there.

She tenderly squeezes her lips against my clit and I cum instantly.


My loins spray a gentle stream of hot cum in Luna’s mouth and face. She drinks it in.

“While you are no heavy squirter, like all werewomen, your body loves to tell your lovers when you’re enjoying yourself,” she purrs as she moves to lie against me right side. She kisses me and we are back to staring into each other’s depths.

“Catch your breath dear, we have a lot to cover tonight before I send you back,” Luna states.

I look up and only see sheets of fabric and white light dominating my view. I forgot, but I am indeed still catching my breath for some reason. The thought of me being sent anywhere else right now seems foreign and terrible. I turn back to Luna and kiss her again.

“Can we try something new?” I ask in anticipation.

“Hahah, of course honey, what do you desire?” Luna responds.

“Let’s try some 69,” I say sheepishly at the thought of this next experience.

“No need to ask me; let your body do the talking, child.” Luna woos me in confidence. “I need some pleasure down there and I want to see what you can do.”

I slowly turn to face her feet and move toward her pussy with a slow, menacing crawl. Upon a close glance of her mons I see her pussy has no hair, razor bumps or imperfections caused by care or hygiene. Her pussy glistens in lust. I need to oblige.

“”mhmmmmmmmmmmmmmmmmmmmmmmmmmmmmhhhhhhm AHMMMMMHHNMMMMMMMMMMMMMMMMMMMMMMM””

We both start licking each other’s sweet nectar. As a man, 69 was not the easiest to do. I was always to long and tall for most of my lovers to try. God knows my cock was stubborn and didn’t like the angle. As a woman, this is just delightful, Luna’s pussy and mine line up perfectly with our mouths.


We moan in unison. I buck my hips against her tongue as it hits my folds like a miniature cock. Her legs nearly crush my head as I lap her pussy. Her cum tastes sweet, sweet like mine, like Gabriella’s.

The thought of pleasing Luna and getting pleasure from her begins to overwhelm me. Such a new feeling is too much for my head.


I cum harder, with a rolling wave of ecstasy. My instinct tells me to keep licking. Luna doesn’t relent.


I cum a second and third time. As the last rush of pleasure crests, I collapse on Luna and roll off her delicate body.

I’m in shock at all the pleasure my body is giving me. No real refractory period, no downtime, no soft cock. As a man, I would have to wait 10-15 minutes to go again, as a woman, it’s almost a complete recharge.

“I know what you want to do next,” Luna coyly suggests. “You’ve always wanted to try this next move.”

I search my memory as a haze of pleasure lifts. Oh, scissoring or tribbing, clam jousting, venus humping, clit-clatting, touching tacos. One of the first things in porn that aroused me so much. One of the first things that awakened my latent desires to share the female form. One of the first things I’ve desired to feel since I wanted to be a woman.

“Yes my sweet daughter, I know you’ve wanted to try the supreme kiss that can only be given between women,” Luna says as she moves her pussy toward mine. “It’s my favorite too.”

She moves her right leg under my left, and I move my right over her left. With gentle inching and moving our pussies finally touch.

“You need to start slow, gentle circles,” she says with a trailing moan. “Let your pussy take control as it builds and follow my lead precious.”

Ohhhoohh, I let out a moan as she starts this charge of pleasure.

I brace my arms against the fabric of the bedding, and let my hips move and gyrate with Luna’s direction. The pleasure slowly builds with each caress of our pussies. With this there is no penetration, no deep thrusting. As a man, I would often be leading the escapades, dominating and thrusting every fiber of my manhood deep within my lover’s folds. As a woman, It is more gentle, as I feel her juices mix with mine, and feel her clit graze mine, sending a building pleasure in my loins. I could best describe it as a feeling of humping silk to my male friends. But I’m happy I have Luna all to myself right now.

““ahhhhhAHHHHHHHOOOOOOOHHHH”” we both moan.


Our pussies are dancing now and I can feel my muscles tensing to keep up this acrobatic position. She moves one arm to grab my thigh and brings her pussy into closer contract with mine. I take it as my prerogative to increase speed and force.


“Ohhhhhhhhh uhhhhhhhh watch your pace ooooohhhhhh AHHHHHH, you’re not a man putting it in me, you can have finesse, oooooohhhhh that’s good.” Luna counsels.

This is the first sex move I never could have performed as a man, at least not like this and I’m loving it. It’s beginning to wear me out though. I wet my fingers and grab her right breast to fondle.

“There you go, sweetie, think like a woman,

Luna purrs.

“Ohhhhhaaaaaaaaaahhhhhhhhhhh,” I moan in return.

I move to match her wet sliding pussy to mine. My nub gets firmer and firmer with each pass. I can see Luna panting in pleasure, sweat covers our bodies as we both do not relent in giving up our dance.

"There we go, YES YES, YOU’RE SO WET, MAKE ME CUMMMM, MAKE ME CUMMMM," Luna commands.

“Ahhhhhhh yessss I need to ccummmm, make me cummmmmm Luna,”’


Faster and faster we edge each other’s pussies, until it hits us both in the most splendid and powerful simultaneous orgasm.


We collapse together in exhaustion, on the bed after our gliding velvet for what felt like an eternity. I slowly crawl back to Luna’s bosom to nuzzle her in comfort and joy.

“Thanks for the best sex of my life Luna, I don’t know what to say or do to show my joy,” I confess.

“I always love it when one our own comes home,” said Luna. “While time has not the same concept here, these homecomings don’t happen as often as I would like, and I certainly savor each moment with my heirs.”

Luna sits up after our moment passes in silence and begins to stand in a dominant posture.

“That was simply the first act my dear soul,” Luna reveals. “To live as a werewoman, is to live as a lover of both women and men. To be free who to love and to welcome you to the sisterhood I must break the bonds of your virginity. After all, how can you recruit future sisters if you do not know how to bed and lie with a man?”

With the finish of her sentence, her clit begins to grow, centimeter by centimeter, inch by inch, her clitoris transforms into a large veiny cock before my widening eyes. A set of balls dangle below her new manhood. I still see she retains her large bosom though.

“I will teach you how to suck a cock, fuck a man dry and leave him begging for more,” Luna says in a dominating tone as she beckons me to my knees. “First I want you to learn how to properly take a man into your mouth.”

Hypnotized by her new member and overwhelmed by my new instincts I slowly drop my jaw and slide my tongue out to lick the tip of her cock.

“Mhmmmmhhhmm, nice and slow, yes my child,” Luna nods in approval.

I begin to lap her huge 9 inch cock like it was ice cream, not sure if I’m ready to let me lose myself yet.

“Don’t be scared, take me in,” Luna commands.

I slide my lips over the tip of her cock slowly in response, trying hard to keep my teeth away from her member.

“Yes, there we go, you get it, keep going, ahhhhh,” Luna responds.

Feelings of sexiness begin to cloud my head. A different new sensation, like now I know I have been gifted the responsibility of pleasing others in new ways. Drawing from my memories of getting blow jobs I try to repeat the same gestures that pleased me.
I reach with my right hand to wrap my index and thumb around the base of Luna’s shaft as I further slide her cock into my mouth.

“MHHHHHMMMMMMM, yes that’s better, let your instincts guide you,” Luna advises as she tosses her head back in a moment of pleasure.

I begin to suck and move my mouth up and down Luna’s shaft, using my saliva to coat her member and lubricate my next actions.

“Atta girl, that’s the spirit, let it fill you,” Luna commends. “Mhmmmmmmm, you’re a natural.”

Feeling the sexy encouragement, I begin twisting and stroking my hand on her cock with the movement of sucking.

“Yesssssssssssssss much hotter, drink me in,” Luna moans. “Cradle my balls for more sensation honey, please.”

I oblige and reach with my left to cup her testes as gently as possible. This whole act feels hot, but fuddles my mind. I never thought to do this as a straight man, but sitting here on my knees sucking, fills a void and makes me feel all girly and sexy. I feel wetness build again in my pussy.

“Yessssss, slowly fondle them, fondle, stroke them, caress me, caress me like a lover you have seduced after a night out,” Luna says with ever increasing pleasure in her voice. “There, keep going, unnhgghhhhhhh, yes yes, suck it.”

Thoughts fill my head, sexy thoughts. I am the seductress, making men whimper and slaves to my body. I am the seducer, the vixen, I am woman, I am a werewoman. With divine inspiration and motivation, the feeling to be the one desired by and above all focuses my attention on Luna stronger than ever. I move my mouth and hands faster, striving to caress every inch of her. I look up for a moment to see her fondling her own breasts, which fills me with joy and pride.'

I’m gonna make her cum her brains out. Faster and faster I stroke, suck and play with her manly loins, letting all vestiges of taboos and doubt fade away.

“Yes, feel the inspiration well unnnhhhhhhgghh inside you,” Luna moans. “You’re gonna make me blow, uhggnnng ahhhhh ahhhhhh ahhhhhh yes, I’m coming I’m coming, I’m coming. AHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHAHHHHHAAHAHAHA.”

In a split second I decide how to handle her cum. Never one to retreat or half ass a job, I keep my mouth on her member and I feel the first spray of her hot cum shoot into my mouth. The sensation stiffens my nipples and wets me further. Her load tastes like sweetness, honey or faint syrup.

A second, a third and a fourth spray hit my mouth and throat. It fills me up and pours out the edges of my mouth. I take my mouth off her cock and swallow her whole load, trying to please the goddess I just served. Never having taken cum like this, I hope that all men taste this delicious.

“Yummmm mmmmmmm” I moan as I swallow the last bit.

“Bravo, my my, you are a go getter,” she says with excitement. “Not everyone swallows on the first try.”
I still feel an empty horniness inside me. I lie on my back and begin to pleasure myself on instinct.

“You know what comes next don’t you, you sexy student,” Luna says as she lowers herself on top of me.

“I got an idea,” I say as I spread my legs wide still massaging my pussy. “I need to know how the other half lives.”

A masculine sensation hits my mind.

“There’s no turning back from here,” my masculine self speaks. “You are about to take someone else into your inner being. You’re losing your virginity all over again. Once she pops your cherry, I won’t be calling the shots anymore dear friend. You are never going to be as whole again. I can’t fight back against this unrelenting tide. Sigh Get it over with.”

He fades as I feel Luna’s cock slowly penetrate my pussy. I wince at the tightness and yet pleasurable sensation hitting my pelvis.

“SHEHHHHHHHS AHHHHHHHHHHHH, you’re inside me, that’s it.” I shudder.

“Not at all,” Luna confesses as she drives her meat deeper into my pussy. “Uhgnnnnnn its tight.”

“AHHHHHHHHHHHHHHHHHHHHHHHHH,” I scream as I feel her cock tearing and spreading my flesh inside.

“Lucky for all my descendants, not much blood, and it’s a quicker change than normal women,” Luna states matter of factly.
She keeps pushing her cock further and further into me until I feel it barely touch my cervix.

“You’re gonna love this next part,” Luna coos.

She slowly pulls her cock back out, and slowly guides it back in, moving it a little faster with each thrust.


“Yes, your pussy is accepting me more and more darling, just let me take you home!!” Luna declares in ecstasy. “AHHHHH uuuhaaa yes, fuck yes, FUCK YEAH!!!!! Be proud of your womanly folds, be proud of your pussy.”

I feel ripples and veins of her cock hitting my pussy lips and wall. She’s filling up every inch of my pussy. My new womanhood is pulsing with pleasure in response. I spread my legs wider in response.

“Feel like a woman… feel sexy……ughhhhhh… have a long life of love and pleasure ahead, sweetie,” Luna says. “Never let anyone make you feel….ughhnn … guilt over what you are…..ahhhhhhh…. Bask in the pleasure, become the girl you were born to be.”


Luna begins kissing me feverishly and I wrap my legs around her to bring her cock deeper inside me.
Harder and faster Luna pounds me, and my body further descends into lust. I hold on and let her lead the pace, trying my best to help her in the throes of pleasure.

"Ohhhhh yes, let me pound that pussy, ughnnn ahhhhhh yes you dirty girl, you love cock, you want my cock, you need my cock,” Luna orders me.

“Yess I love cock, yes I love sex, I love my pussy, I love my breasts, my smooth skin, my dainty hands, I love, I love pussy, I love pleasing others, I love men, I love women, I love pleasing others, I love pleasing myself,” I confess as my body burns with the beginning of another orgasm.

“Who are you?” Luna asks.

“I’m Nate,” I respond meekly.

“Noooooo!” her voice booms with a tremble.

“I’m Nat…..Nat……Nata….NatashaaaaaahhhhhhhhhhhhhhhhoohhhhhhhhhhhhhHHHHAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA”

A new orgasm wracks my body, giving me the feelings of womanhood in new ways. My head spins as her pulsing member brings me too many orgasms to count.

“Yes Natasha, let me give you what you’ve been owed your whole life,….unnnghhhh. You are mine….ushher in a new beginning and be the woman were meant to be…. AHHHHH AHHHH UHHHHH AHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHUUGHHHAAAHH AHHHHHHHHHHHHHHHHHHWOAOOAHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!!!!!!!!!"

She cums inside me, filling me up deeply with her warm essence. I quiver uncontrollably as she looks into my face and smiles. Her hands caress and brush away the sweat and hear from my face.

“You did wonderfully,” she says before kissing me. “I can’t wait to see your future.”

“Thank you Luna for giving me this,” I say with a drained tone in my voice. “I don’t know how to ever thank or repay your love.”

“Sure you will dear,” Luna responds. “Live a full life and return to me when the time comes. You need to return but I will always be watching over you.”

Luna places her hand on my chest and a white energy blinds my vision and focus.

After a moment of solitude in my thoughts, my vision slowly returns. I think I see a person, a face, a woman’s face staring at me. She’s blonde, I see she’s in blue cammies.

“Gabriella?!!!!!!!” I shout inside my head. I can’t move or respond.

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