Risky Roleplaying

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Doing some Risky Roleplaying with a new friend.
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Part 1 of the 2 part series

Updated 06/09/2023
Created 10/12/2018
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After booking my flight for the dates Mary suggested sending her my itinerary and getting a text back with a calendar showing the date I would arrive with a big green "O" one days later making it clear how fertile she would be and how risky the roleplaying would be knowing I would go wild thinking about being with her again and would be like an insatiable wild animal when I got her alone after having a full four weeks to think about all the sexy things I want to do with her.

The excitement of seeing her again is so amazing that I feel my heart beating fast as I take in Mary's beautiful smile as she drives us home from the airport. While she drives I am admiring her obviously braless breasts erect nipples and sexy curves in the silky sundress she wore knowing how much I love the way she looks wearing them and that I cannot resist touching her sexy body when she wears them.

My cheeks already ache from smiling so much and the feelings so intense that my hands shake as I place my left hand on her right knee without conscious thought until I hear a soft moan escape her kissable lips. The second I touch Mary's knee and slowly slide my hand around to the inside of her leg even before I start to gently slide my hand up the inside of her silky soft thigs I feel my cock starting to swell with desire for her.

By the time I reach her inner thigh and press the side of my hand against her swollen lips quickly noticing how naughty she is leaving home without panties my cock is rock hard and throbbing with desire as I feel her delicious nectar coating my fingers in slippery juice and I hear her moan out loud inspiring me to explore further. When my fingers dip into her slippery pink playground and I hear her sexy moan of satisfaction I can't help myself and start kissing her neck and sucking her ear lobe when she stops at the next intersection causing her to push her tight wet pussy against my fingers longing for deeper penetration.

As soon as the car comes to a complete stop Mary's hands go straight from the steering wheel to the back of my head pulling me into a deep passionate kiss as our tongues dance the tango until we hear horns honking and break our kiss to look around and see everyone in the cars around us smiling and giving us thumbs up as we drive away from our appreciative audience. I can't help but notice the sexy sly smile on her beautiful face and her perfect erect nipples as she quickly head towards home.

I thoroughly enjoy teasing her wet little pussy as she tries to concentrate on driving us somewhere private where we can get our hands on each other and do everything we have dreamed about while we were apart. I suddenly remember how amazing she tasted the first time we were together and quickly pulled my slippery wet fingers from her tight grasp to sample her sweet nectar. I see the huge smile on her face as she watches me tasting her slippery juice that drips from my fingers.

The thought of Mary tasting her own juices turns me on so much that I dip my fingers back inside her tight wet pussy until they are dripping in sweet nectar before sliding them into her sexy mouth as she tries to concentrate on her driving. It makes me so horny watching her passionately suck her sweet juices from my fingers and hearing her moan makes me dip my fingers back inside so I can taste her again as I hear her ask if I brought the camcorder so we can video our love making and watch it later.

We are both so excited that the rest of the drive to her house is just a blur of stop light kisses and finger snacks until we arrive and quickly head into the house. I can tell how excited Mary is as she gives me a quick tour of her house on the way to the master bedroom and then on to the master bathroom where she leans against the counter next to the sink as I start kissing her running my hands over every inch of Mary's sexy body.

I lean back to admire her amazing curves and notice a sly sexy smile forming on her face as she bites her lower lip and reaches down to the bottom of the sexy dress she wore for me slowly sliding the bottom hem of the dress higher until I see her beautiful pussy come into view and as I look into her eyes and she looks down at the counter with the shaving cream, razor and wash cloth laid out and ready while she says.

"Sugar I think you said this is one of your fantasies. Would you like to shave my little pussy nice and silky smooth before you taste me and have your way with me?"

It is such a turn-on to shave Mary smooth and bare that before I am finished I notice her inner lips glistening with sweet nectar and my erection is so hard it aches and throbs as she gives me an amazing kiss and a quick stroke of my cock before directing me to take a quick shower and meet her in the bedroom.

While I am showering I cannot wipe the smile off my face thinking about Mary making two of my favorite fantasies come true by picking me up at the airport wearing a dress without panties and then asking me to shave her smooth before I remember that she is setting up the camera to video our reunion and most likely some amazing love making that we can watch later as I feel my cock throb with anticipation of fulfilling another fantasy.

I enter the bedroom freshly showered to find one of the sexiest scenes I have ever dreamed about as I take in my surroundings I see Mary on the bed sprinkled with red rose pedals naked except for the thigh high stockings that make her great legs look so sexy. I notice the candles lighting the room creating a romantic atmosphere and sexy mood as well as the video camera at the foot of the bed already recording the beautiful scene in front of me.

I notice Mary on her back laying sideways on the bed with her head just hanging over the edge and I can't resist approaching her and kissing her sexy lips upside down as I take in her amazing breasts and perfect erect nipples begging to be licked and sucked. I can't resist touching and exploring her sexy body with my hands and lips and take a short break from our kisses to suck her sexy nipples getting them hard and wet before sucking cool air in around her nipples making them delightfully sensitive to my touch.

As my lips and tongue explore further down her amazing body I feel her turn her head and take the tip of my growing erection between her lips and swirl her hot wet tongue around the head as I continue growing to full thickness and length as she continues her oral magic. When I feel Mary deep throat my entire cock before it gets fully hard I realize she is trying to fulfill every one of the fantasies on my wish list tonight knowing I have never had someone go deep enough to take the last two inches and have dreamed of feeling lips gripping the base of my shaft.

It was at that moment I realized she is the woman I have always dreamed about and fantasized about marrying and I was determined to make sure I granted every fantasy on her wish list too. Watching her lick and suck my big hard cock reminded me of how much I love the way she tastes and I place one knee on the bed beside her head to get my tongue in her tight little pussy.

The sweet taste of her feminine nectar on my tongue is like an aphrodisiac that quickly brings me to a full throbbing erection as she continues teasing my hard cock with her lips and tongue. I get so turned on tasting her sweet little pussy while she gently sucks and licks my rock hard cock that I have to pull away for a moment to keep from cumming and ending our fun too soon. At this point she starts teasing me roleplaying some of the hot sexy things we have talked about saying.

"Oh Honey are you getting close already? Did you save up a big load in the last two weeks like I asked you to? Are you thinking about how hot and risky it would be to let that huge load blast out while you are pressed against my poor little cervix? You know I'm unprotected so you can't cum inside me right now unless you want to knock me up right baby? Are you thinking about how good my tight unprotected little pussy feels when you are bare and balls deep with my slippery cervix kissing the tip of your big hard cock? "

I look back at the sexy smile on her face as I watch her gently stroke my shaft slowly coaxing a huge drop of clear slippery precum to gather at the tip and start sliding down the head to gather around the ridge causing me to moan in pleasure from the amazing erotic scene. Just as we make eye contact I see a sexy smile as she extends her tongue and gathers the precum from around the crown coating her lips and tongue as she says.

"Honey it would make my pussy so wet if you show me how much love me by kissing me with your nut butter on my lips while you rub that big beautiful cock against my clit and whisper how sexy and beautiful you think I am until I cum all over your cock."

My extreme desire to prove my love for Mary takes over and without a moment's hesitation I spin around sliding between her sexy smooth legs aligning my throbbing shaft with her swollen labia as I attack her sexy lips and tongue with passionate kisses beaming with pride at the sexy noises of appreciation she rewards me with knowing later I will return the favor and be kissing her with my lips drenched in her sweet nectar.

Kissing her neck and ears as I whisper sexy things along with sliding my ridged shaft between her hot wet labia rubbing her swollen clit at the end of each stroke quickly brings her to two intense orgasms as precum leaks from the tip of my hard cock coating her outer lips and clit with my slippery juices.

I follow her eyes as her gaze drops to the nectar glazed shaft of my hard cock as she tilts her hips and slides her hot wet peach against the bottom of my shaft making us both moan at the delightful pleasure emanating from the spot where we become one with each other. Her pussy is so beautiful wet and swollen and my cock has never looked so big and hard as it does now sliding through her slippery pink lips making sexy sounds of juicy passion.

As Mary tilts her hips sliding her pussy from the base of my shaft to the tip we both notice a big glob of clear precum ooze from the opening on the tip of my very excited cock to drool right onto her engorged clit before sliding down towards her pink inner lips causing us to both moan and make eye contact when she whispered "So risky but so hot and sexy"

I look deep into her beautiful eyes and say. "Baby I love you so much and I can't resist your sexy body, I can't wait to be inside you." I love the little sexy moan she makes when I change the angle slightly and the tip catches in her tight opening before slipping past and pushing hard against her slippery clit increasing the excitement for both of us as she says.

"Oh Honey I want to feel every inch of her big hard cock deep in my tight little pussy too but I'm so close to my ovulation so fertile and you have two weeks of potent sperm just waiting to drown my poor little egg and fertilize it. Are you sure you can control herself and not get carried away and cum deep in my pussy and knock me up?"

Just hearing Mary say those words excites me so much that I feel my shaft jerk hard and as I look down at the head as it slides up through her juicy lips I see a glob of thick white sperm ooze from the tip and pause there until she looks down and quickly scoops it up with her finger and with a sexy grin she places it on her tongue as she pulls me in for a quick kiss before whispering in my ear.

"We both know that was not precum Baby and we both know that I am at or just getting to my most fertile time of the month and you have a huge load of highly motivated swimmers that would love to go hunting deep in my little pussy for my fertile egg. This is about as risky as it gets honey just like your fantasy. I need to feel your hard cock deep inside me with no protection so why don't you put just the tip in and see if we have enough control to get the whole thing in my tight wet pussy without impregnating me."

From the moment I first saw her at the airport looking so beautiful and sexy in the silky sundress with no panties and gave her that first kiss she has had me more excited than I have been in my entire life with all of her sexy teasing and roleplaying and I thought she had me as excited as I could get until Mary whispered the most erotic words I have heard with her lips tickling my ear she said.

"Honey you are so strong willed and the kindest sexiest man I have ever met and I truly love you but it would be the most erotic thing I have ever experienced if I can use everything you taught me to break your will to do what you know is right and seduce you into losing control and let your inner beast out. I trust you and if you truly love me the way I know you do than have your way with me and if you really want to mark me as yours then press the tip of your big hard cock against the unprotected opening to my womb and fill me up with every drop of baby batter you've got."

I am still taking in everything she whispered in my ear as I feel her tilt her hips and align the tip of my very hard cock with her tight pink opening and with another quick tilt she pushes the head just inside clamping down behind the thick ridge to lock me tightly inside her passion flower.

I feel her soft feet caressing the sides of my legs as she rotates her hips teasing the opening to her slippery pink inner lips with the tip of my throbbing erection until I feel her heals hook the inside of my thighs and with a quick timed hip thrust and a pull behind my thighs with her feet two more inches of my shaft sink deeper inside her tight pussy.

I feel her passion build quickly as her hands grab the hair on the back of my head pulling my lips against hers as she kisses me aggressively while doing what feels like a corkscrew motion with her hips as she pulls with her heals until I feel her soft hands tracing down my back and feel her grip both of my firm ass cheeks for more leverage to pull my cock in deeper with each rotation of her sexy curvy hips.

I feel the head of my cock hit the back of her tight little pussy hearing Mary moan into my mouth as we continue our amazing kisses and with one more lunge of her hips and a pull with her heals and hands I feel the last inch slide inside filling her with the full eight inches of rock hard throbbing cock.

As we kiss I feel her lips forming a sexy smile when I notice her moving her hips like she is trying to find something until we both feel it and like a jolt of electricity we both moan out breaking the kiss as we look at each other with surprise and feel the tip of my cock tickling the opening to her cervix triggering overwhelming stimulation in both of us that feels like we are connected electrically with the slightest movement causing amazing sensations.

I see a smug sexy smile on her lips as she looks deep into my eyes and gently flexes her sexy hips pressing the opening to her womb against the sensitive tip on my excited cock making it jerk hard deep inside her tight pussy as she slowly moves her lips to my neck and does that sexy wet neck suck and kiss thing that she knows turns me on so much when she does it that it makes my cock so hard it throbs. It feels like the opening to her cervix is trying to suck in the tip of my cock as Mary pauses the teasing neck kisses to slowly whisper in the sexiest voice against my ear.

"Michael ...tell..me...where...you're...big...hard...cock...is...right...now?"

I feel her pussy squeeze my shaft tighter as I answer. "Sweetheart every inch of my hard cock is as deep inside your tight little wet fertile pussy as deep I can get right where it belongs."

I feel Mary tighten her muscles again and rotate her hips rubbing the slippery opening to her cervix around the tip of my cock making us both moan out loud as she whispers in my ear.

"Is this as exciting as you're fantasy? Does it turn you on knowing you're deep in my tight young fertile pussy just hours away from ovulation with the tip pushed into the opening of my cervix drooling fresh potent sperm inside my womb? Is this risky enough Honey or would it turn you on even more if I told you I didn't get on birth control like we talked about because I started to get excited by the stories you were telling me about risking pregnancy by having you cum deep inside me close to my most fertile time of the month?"

All her squeezing grinding sexy roleplaying whispering in my ears and kissing my neck has got me so close to losing control I have to give her several deep hard thrusts to change the stimulation to keep from cumming before I'm ready but as soon as I get it under control she starts rolling her hips and kissing my neck one moment before she switches to whispering naughty things in my ears teasing me and roleplaying. I switch to long deep strokes pressing in hard at the end of each to quickly bring her to another orgasm as Mary moans and whispers against my ear.

"I can feel your cock getting thicker and harder Michael, I know you're getting close and we both know it's going to be a huge load. Baby, are you really going to pull out before you cum? This is your fantasy. I picked you up from the airport with the silky sun dress you love so much with no bra and no panties so I could tease you and you could play with my wet little pussy on the way home. You shaved my pussy smooth and bare so it feels great on your tongue and it will look so sexy with your sperm dripping off of it or even better leaking out from between my puffy pink lips after you cum deep inside me and the video camera is recording so we can watch it again later."

"I have only let my ex-husband cum inside me unprotected and bare two times and both times I got pregnant from just one shot and you cum quite a bit deeper and so much more than he did. I can't stop thinking about how amazing it would be to feel you explode deep inside me especially knowing how much you ejaculate when you are excited and I know you are beyond excited thinking about how risky this is with your big hard cock so deep inside my young tight little fertile pussy pressed against my open cervix leaking potent sperm and just moments away from draining a two weeks supply of very motivated swimmers straight into the opening to my womb."

I realized how much we have in common when she started experimenting with roleplaying to turn me on and then we both learned that it turned her on just as much when we discovered how quickly she gets wet when she talks about making me cum deep inside her tight fertile pussy. I feel her tensing up again as she starts another orgasm and I push in deep against the back of her pussy to stimulate her a little more and give Mary an epic release and out of nowhere I feel myself quickly slipping past the point of no return as I hear her say.

"Oh baby I'm going to cum all over her big hard cock again and I feel you throbbing up against my cervix too, I want to feel you cum with me, and I want to feel you cum inside me, cum deep in me now baby."

I feel the first hard pulse and quickly pull out of her very tight spasming pussy just before the first blast leaves the tip of my cock and we both look down to see if I made it out in time before the first volley erupted. I watch the first blast lay down a thick white stripe perfectly from the very top of her labia straight up her tummy and across the inside left edge of her right breast just missing the nipple and ending on her lower lip.

I somehow managed to get it back under control after the first squirt and just a small stream of thick nut butter slowly leaking from the tip to puddle just above her engorged labia as we both tried to get our breathing under control. I lift up and sit back so I can see her beautiful pink pussy still gapping open slightly and the huge sperm trail running up her sexy body as I watch Mary slide the index fingers from both hands down to the top of her pussy hooking both fingertips inside the opening and pull up and out opening her tight little pussy up so I can see deep inside as she asks me.

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