When Annie made Me Lucy Pt. 09

When Annie made me Lucy - Part 9

Authors note: This is best read in the right order. Annie and I met at work and found we both share the pleasure of sex in lingerie. Having spent the weekend at Annie's and dressed fully in front of a woman for the first time I have been out as Lucy, played with shop assistants and had fun with a shemale maid. Having had sex at a charity auction and licked my cum from my girlfriend we return to meet the hypnotist friend who helps Annie feel her 'cock' is real before she fucks me.

Note - this will always be a story back and forth. It has annoyed some readers, sorry about that but its what it was and it would not do justice to my lovely co-writer to try to only give this from one perspective. If that isn't for you... pass on by

Annie

You can tell your agreement pleases me as I passionately kiss you back, earning scattered applause from the other auction guests who had begun to come out of the building and wait for their valeted cars. When our kiss ends, my face is just beaming into yours and you know it isn't about any particular sexual exploration.

Our car arrives at that moment, as if on cue, and I quickly whisk you away. Reaching home, I see that Penelope's car is already there. We park and enter the house to find her chatting with Marie who has served her some wine. We are all smiles, hugs, and cheek kisses as we greet and get some wine ourselves.

"You are both knockouts!" exclaims Penelope, feeling a bit drab in a well cut grey dress with a blazer. "Did you go to the big charity auction?"

We fill her in on the event, all the beautiful people, the amazing things and experiences being auctioned off, and such. Neither of us choose to reveal our private play to her and we soon settle down to business.

"Annie, you told me you would like to have a special suggestion given to you, to enhance your love-making," Penelope starts off very clearly. "We've talked about this in our sessions and I know what you want. Is that still the plan?"

"Yes, very much so. Myself first and then Lucy can let you know if she wants to have the companion suggestion added for her."

Penelope nods and allows me to lead her to our living room. I get comfortable on the couch with her next to me as you find a chair to watch.

"Annie, I'm going to take you through our 'forest path'. Are you ready?"

"Yes, all ready." I close my eyes. Penelope's voice is soothing as she begins to walk me through.

"Annie, you are on a forest path. Feel the cool, shady air and smell the leaves and pine needles. Walk forward on the path and feel yourself relax. As you walk further you will become more relaxed. When you reach the clearing with the pond, you will be completely relaxed and in the suggestive state...."

Afterwards you tell me that after a minute or two of her quietly leading me ends with my confirmation that I had reached the pond. In the distance I hear Penelope continue.

"Annie, I'm going to let you in on a secret. You are a very desirable, beautiful woman, but you have something more. When you put on your strap-on harness and fix your favourite dildo to it, you will realise that you actually have a large, beautiful, fully functioning cock. When you touch your cock, you will feel how sensitive and pleasurable that is. You will find yourself easily erect. Every sensation your strapon 'feels', you will feel as if it were your full cock, all the stimulation and pleasure of it. When you orgasm, your balls will get tighter and tighter with increasing intense pleasure for several seconds and then your cock will erupt with cum, lots of cum in thick creamy ropes. Your cock will be ready to orgasm and cum that much again as soon as you are ready to have another orgasm. Your cock will disappear when you take off the strapon harness, leaving you with your natural body in all ways. This will happen every time you put on the strapon harness and that one special dildo until you ask me to make this go away. Do you understand?"

"Yes, I understand," I reply slowly.

"Good., well done. Now slowly walk back along the path and in ten steps you will wake, refreshed and ready for a long night of lovemaking." Penelope winks at you at that last bit. "10... 9... "

When my eyes open, I'm a bit flushed but look energised and enthusiastic.

"Did you?" I ask, looking at Penelope.

"You're all set, honey. I hope you enjoy it."

"I'm sure I will. I've always wanted to know what it felt like to have a cock. Now," I say, turning to you. "Do you want to see and experience me as if my strapon is my cock?"

Lucy

It's been a fun night at the auction and your arousal is clear when you kiss me, gaining attention but in a good way, and I know why. I too am aroused, though the folds of my dress are helpfully hiding it as we drive home.

Marie is entertaining Penelope when we arrive, and she is a perfect host, though her sexy stocking tops are just occasionally visible as she deals with our needs and then retires. As I watch you get taken through the process it takes its time, though for you I can see it went quickly. You smile at me and ask me if I want to experience you as if your strapon were real... and here it is, my choice. I can go with you as Lucy and let you alone enjoy the feelings Penelope has engendered in you, knowing from my sensitive breasts how good she is and how aroused you will be... Or...

"Penelope... let's do this, for Annie as much if not more than for me... whatever the other part of this is... take me there."

I get aroused even more by saying it, and the smile on your face makes it all worthwhile, my cock erect at the thought of making my girlfriend happy

Annie

Both Penelope and I smile and she ushers you to the couch. You relax, yawn, and hear her ask you if you feel refreshed?

You do, actually. You feel energised and your appetite for me seems even higher now. Just like before, you don't remember the process.

Penelope gives us each a warm hug and quick kiss before departing for the evening. Marie seems to be scarce and I take your hand. "No more waiting... I want you..."

Lucy

I hear Penelope ask me if I feel refreshed and I realise, with a start, that she is finished with me, yet I cannot recall anything she said or did. As she is leaving your hand snakes into mine, and we close the door and embrace. I do feel somewhat refreshed I realise, and when you say you want me, I tremble a little. You sound so urgent, passionate and in charge. We kiss hungrily even before you start to pull me with you upstairs to your... maybe our??... room.

I feel aroused, your body turns me on so much I can't wait to enjoy it, for you to enjoy mine. My nipples feel more sensitive than I can remember as your hands play with my tits and we kiss again. Your ass feels gorgeous through this silken, form fitting material the red dress is made out of but you soon stop me.

"Oh no... you can wait a little... you, my sexy Lucy, are mine and you offered yourself up so this should not be a surprise."

I melt into you again, letting you lead, knowing where it will end but not how, and already my cock is hard and ready to fill you whenever I am allowed, but somehow I don't think it will be quite yet

Annie

I lead you into our bedroom, kissing and fondling you. "Do you want to leave your dress on?" I ask with a smile, and you nod, demurely.

"You get comfortable, lover, I'll be right back." I enter the walk-in closet and you hear me rustling around a bit. You hear me moan loudly at one point. After a few minutes, I return with some things in my hands but what captures your gaze is the bulge in my dress. There is no mistaking this for some mere strap-on... I now have a beautiful big throbbing cock and you have made me very erect.

I attempt to ignore my erection as I get on the bed with you. I have a wet washcloth and a bottle of lube. Laying next to you, kissing you, I begin to work your panties down until they are bunched tightly around your knees. My hand begins to caress your beautiful, femme ass, massaging your hyper-sensitive, smooth skin until you moan in need. Almost symbolically, I bathe your bottom with the washcloth, tender, and loving. I begin to massage your cheeks and inch my fingers closer to your 'pussy'. I start applying lube all around your opening and eventually you feel one finger begin to gently press, slick with lube. You sigh as your body relaxes and my finger sinks inside you. I slip it out and in, over and over as I work you with lots of slippery lube. At one point, it squelches.

"You are so wet, my lover..." I moan and that is what you feel... that all this lubrication and wetness is from your arousal and it feels incredible.

I gently move a second finger into place and as we make out I work them both, relaxing you further... you gasp when three fingers slip into your pussy and you are gripping my other hand knowing you ache to be filled, to have more.

That's when I take your hand, move it slowly between us and you wrap your fingers around my hot, throbbing beautiful cock...

Lucy

"Yes, please leave my dress on, that feels sooo sexy", and you smile before heading to the closet.

Your return.. fuck you look amazing, sexy, stunning in your dress still but something pulses underneath it, and I find myself desperate to know what it is.

As you turn me over I know what's going to happen and I know I want your cock. The feeling as you lube my pussy is indescribable, teasing, slippery, and then a finger... fuck... aaaahhh.. that feels good... oooohhhh... god why have I waited so long for you to do this.

As you work me wider I hear my pussy juices and I know my cock is piston hard as you fill me with a third finger. I reach under your dress and find the throbbing member you have hidden away and wrap my hand around the base. Such a powerful cock you have, and I slowly draw my hand up to its tip - my that's a nice size too - and back down. Getting a feel of its length and girth, not too thick for my first time but thick enough and my pussy clenches on your fingers at the thought.

I lift your dress and look at the shape of your cock, loving how it juts out from your sexy body, your tight thighs ready for action still wearing the barely there hold-ups I was stroking in the auction. I work your cock as I would work my own, loving your moans as you feel me play with your throbbing member. I can't believe how real it feels, and how beautiful and sexy it makes you look. I slip my hand down and find your wetness, the situation is arousing us both, my precum is easing out of my tip under me, your juices are flowing.

Something comes over me, I have a desire to suck the tip of your cock even as you fuck my pussy with three slippery fingers squelching in my juices. I lean towards you and ease down, opening my lips and feeling the warm head of your long sexy cock slide between them.

Annie

I prop myself up on my elbows so I can look down my body past my heaving breasts to see this beautiful cock as part of my body... it feels... amazing!...like I have an 8" clit aching to be touched and fondled and sucked...

You realise all of this... you know... you lean into me and open your mouth and I gasp as I feel your lips and tongue on my tip. My body shudders and I feel myself getting very aroused. I watch you exploring how to do this, knowing what you like, how it feels. You are hesitant at first but then enthusiastic. I know I won't last long with all this new pleasure but I also know that I won't have trouble getting hard and cumming over and over.

Lucy

I feel like I have never seen anything more arousing - a firm female body sheathed in red, long limbs in sheer nylon and full ripe firm tits with bullet hard nipples... and a throbbing cock jutting out from your smooth pubis... I cannot hold back and lower my mouth further down, taking more of your member in, experimenting, sucking a little and tasting the end. This has to be a real one... my mind and yours are convinced this cock is real and I bring a hand around to grasp the base and I ease back and swirl my tongue around the head again and again. As I do I hear you groan with pleasure, every movement of my mouth on your cock is transmitting pleasure straight to your clit.

How much can I get in? I have never had such a thought before but with your cock already in my mouth and filling it so much it seems a natural follow on. Grazing my teeth on your 'flesh' I slowly ease back off and hear you hiss in delight, everything I do transmitting electric sensations to your core. I slowly suck you in again and keep going, marvelling at how good it feels to have your cock, your throbbing hot flesh in my mouth. I gag a little as your tip hits my throat and I am full.... not as full as I want to be but somehow I know we will do this many times even in this coming week and I will practise with your help... your guidance as my own cock twitches at the memory of how it slid into the tight confines of your throat.

I start to bob up and down and move my hand in a rotating slow accompaniment as I coat your cock in my saliva. I barely notice the three fingers you still have wedged in my pussy as I revel in feeling full at both ends. Your moaning gets louder and you are writhing beneath me, panting and groaning as if I am hitting all your pleasure buttons... I want to slip a finger or three inside your pussy now to see what happens...

Annie

I never imagined it would feel this good... I don't know if it is the result of a build up of suggestions Penelope has made in me but I am completely convinced... I have a big beautiful, throbbing cock and you are sucking it like a pro... I can't control myself, moaning, writhing, clawing at the bed as my mind is overwhelmed with sensations... it's like you are giving my clit a blow job...your hand slides between my legs which I spread eagerly... your fingers move inside me as you suck and tongue my cock and I am already past the point of no return...

A single "oh god!" from me and my hips buck, you feel my pussy clamping repeatedly on your fingers inside me but you also feel cum fill your mouth

Lucy

The sensations are overloading you, and I can already tell that you are close. I am sucking your cock, warm hard flesh to my Penelope trained mind, and you are thrusting slightly trying to fuck my mouth. Two, then three fingers slide wetly into your dripping wet pussy, and you groan louder and start to cum. A loud "Oh god" and I feel you simultaneously clamp your pussy around my deeply inserted digits and thrust your solid shemale flesh to the back of my mouth and cum loudly.

As your pussy contracts your cock erupts, I don't know how or what but I feel the amazing sensation of a spurt of warm sticky liquid hitting the back of my throat. As you thrust and cum, I ease my mouth back a little and let spurt after spurt of your cum fill my mouth. I don't know what it feels like to you, but the power of having your hot flesh fill my mouth is amazing and as the spurts get less and your clamping on my fingers eases I swallow the copious fluid you have deposited into my girly mouth. Some trickles out and I catch it with the fingers of the hand that your pussy just let go and feed our cum to your waiting lips.

I have never felt such a sensation, Penelope's gift is amazing as I feel you have a real cock that is staying hard even after shooting a load. The taste was slightly salty yet sweet, and not unpleasant as I drank your cum down. I realise your fingers had left my pussy as you shrieked your orgasm and I feel empty but sated, amazed by the feeling of giving my first blowjob to my girlfriend

Annie

"Oh. My. God..." I breathe, looking at you with eyes still a little glazed from my orgasm. "That felt amazing... you're so lucky...and you are so good at sucking cock! You've never done it before? I can't wait to feel your mouth on my cock again and again... are you okay? I know this was a boundary for you..."

"Sweet Annie, that was amazing," you whispered somewhat dreamily. "I loved that you had a cock and yours was the first, it's kind of a boundary but less so... because it's yours and you have an amazing mind and body and somehow we added a cock that felt, well, real... and I didn't mind, in fact it felt really good how it pulsed in my mouth... but... it aroused me most because looking up as you came I saw my beautiful girlfriend, almost a shemale... and it was your cum filling me... how did that happen? Where did it all come from?"

"You know, I think I'm 'ready'..." I say softly as your fingers continue to toy with my cum-slick cock. "I want you..." My fingers return to your pussy, slipping in easily and moving in and out...

Even as you gave your answer my fingers found your pussy, and slid oh so easily back in as you stroked my still stiff member. As I say I want you I am surprised when you lean across to kiss me deeply, saying, "I am all yours today remember, so if you must have me... gosh, I have to say yes", and you smiled again.

"As for sucking your cock again, I think we have over a week together now, that seems like plenty more chances.." and with that you let me take over.

We kiss and caress each other for a time, enjoying each other's bodies beside and on top of each other. My new stiff cock is never too far out of mind and your hand tends to find it to feel it and stroke it. Eventually, my arousal is growing more urgent and I gently urge you on to your back. I push the skirt of your dress up and pull my dress up until my cock is once again free to the air. I cup my breasts as I kneel between your legs, smiling and enjoying how much you like to look at me, watch me.

I take your knees and move you into position, legs spread and in the air. I slip a pillow under your pelvis, raising your bottom. I can't help but admire the view of you, so ready to have the full girlfriend experience, my hand happily stroking my cock. I shift forward, allowing your ankles to rest on my shoulders as I aim my cock for your 'pussy'. I move slow and gently, teasing you with the soft, hot flesh head of my cock, sliding around in all the lube. Slowly, I get more serious and press it to your pussy, gentle pressure, patience...

When my cock sinks into you I gasp with the pleasure of it and once all the way in, I freeze, feeling the tightness of you around my flesh... hot, tight, and 'wet'. My balls press against your body by your opening. my breasts press against your thighs giving you a wonderful view of my cleavage. I reach out around your legs to stroke your breasts through your dress and caress your face before slowly moving back to thrust in again.

You are eager, relaxed and slick so in no time I'm in a delicious fucking rhythm, thrusting my cock in and out of you, our bodies trembling each time I sink in all the way...

Lucy

As I stroke your cock I know what's coming and I know I want it. When you lift my dress up and get me into position I am nervous but aroused, my smooth cock and balls in plain view for you as you lift my legs and prop my hips up ready. You look magnificent, the sexiest, most erotic sight I think I have ever seen - gorgeous full firm round orbs, nipples trying to push through the fine fabric, your lovely smile and there it is, your cock, the one I just sucked to an orgasm and enjoyed myself doing so.

With my ankles up around your shoulders you take your time, and I gasp as your warm cock head finally penetrates my pussy, my ass, for the first time. Your preparation pays off as I feel no pain, just a fullness that I have never felt before. Then you ease it in and fuck, no... never.... wowwww, fuck... aaargghh oh my god... what a set of feelings as more and more of your solid length fills me up. I cannot believe, I watch your face as you enjoy the feelings of my tight passage gripping you, every sensation transmitted to your clit. Oh fuck, finally your 'balls' hit my ass and I have it all in. I didn't realise it but I was holding my breath and I exhale as I feel the whole length of your hot hard cock inside me for the first time. I reach for my own cock but you shake your head, and I grin ruefully as you slide a little way out and back in, slowly starting to fuck me.