Risky Roleplaying - Prequel

I am a beautiful, curvy, 42 year old, divorced mother of two that has always dreamed of meeting a man that would treat me the way I like to be treated. I want a man who is a great communicator, but also knows how important it is to listen.

My first husband was a great father, and an all-around good guy, that just didn't quite know how to rock my world, and ring my bell in the bedroom, the way every healthy woman fantasizes about. Like most women I wanted someone that would make me feel special, and maybe even put my pleasure before his, from time to time.

As luck would have it, I found exactly what I was dreaming about, when I least expected it. I took a vacation to visit friends half way across the country, spending some time relaxing and enjoying the sights.

I got a little bored after a few days waiting for my friends to get off work, each evening, so we could go out and see the local attractions, so I decided to check out the Activity partner section on Craig's list.

I found an ad from a guy that was looking for someone to go hiking with, or just check out the different events the town hosts on the weekends. I decided to send him a message and see where it goes.

I thought it would be fun and exciting to have someone to show me around and hopefully, have some great conversation too.

The texts went so well, we were soon talking on the phone, making plans to meet for dinner some place nice, so we could meet and talk, to see if we were compatible and would enjoy each other's company.

We met for dinner that night, it was so nice and relaxing with great conversation, and he actually knew how to listen when I spoke too. We spent more than two hours talking and it flew by so quickly, it felt like ten minutes.

I was a little worried about the difference in age between us, but was pleasantly surprised when I saw him for the first time. Even though he is 57, he's in great shape for his age, as well as healthy, active and quite easy on the eyes.

Our dinner meeting went so well, we decided to head over to a nice park nearby, with a scenic lake to walk around and talk some more. It was like the most perfect dream date, he wasn't like most guys that are in a hurry to get to the sex as quick as possible.

He was kind and patient and asked the right questions, letting me know that he is a caring person, and genuinely cared about my views and opinions.

We walked around the lake talking and then he reached out and held my hand, at just the right moment, like he knew what I was thinking, or was just very tuned into the signals I was putting out. After a lap around the lake, he walked us over to a nice quiet grassy hill to lay and watch the sunset together.

Everything he did felt so smooth and natural, that it was perfect when while watching the sunset, my mind started to ponder if he is a good kisser, then again as if we were thinking as one, he leaned over and gently took one finger, sensually tracing a line from my shoulder to my neck, before sliding up to my ear for a brief caress, moving down my jaw line until his finger, paused on my chin, and he guided my lips to his in the most passionate first kiss, I have ever dreamed of.

It was like the princess fairy tale fluff we read about as girls, and hoped we would someday, find in real life. The kiss was everything a first kiss should be, slow passionate sexy and patient.

I was dripping wet and wondering, if this guy is this good at kissing and knowing what women crave. I couldn't help but wonder what skills he might have in the bedroom.

It was the most perfect first date, with a beautiful sunset and a simultaneous moon rise, out of this world kissing that left me primed, and wanting more.

He had to pick up a friend at the airport by 9:15, so we had to cut our evening short, but it was obvious that he was interested, and wanted to spend more time with me the following day.

We made plans to meet the next morning and I got a nice hug, as I felt a sizable erection growing against my thigh, he gave me the most wonderful goodnight kiss, so erotic that it made my imagination ponder weather, this would be just two people getting together to see the sights, or possibly something more intimate. My heart and my very wet pussy, were voting for some passionate intimacy.

He picked me up the next morning, and we decided we would take a scenic drive up to Lake Tahoe for the day, see the beautiful scenery, and get to know each other. We had to stop and pick up a few things at the store. Stop by his place to get beach stuff, and an ice chest for the day trip, before we headed up to the lake.

As he finished packing the essentials, he casually reached over with his hand, and with a firm gentle caress of my neck, he guided my lips to his and gave me a kiss that made my nipples, instantly hard.

The kiss only lasted a couple of minutes and I was soaking wet, as I felt him getting hard and pressing against my thigh, before we separated lips, with a soft little moan from me and a sexy smile on his face, I pushed him back onto his bed straddling him, while I unbuttoned his pants.

I knew he would be a gentleman and probably wait most of the day, before getting to the intimate stuff, and I just couldn't wait all day to see what I was going to feel, deep inside, my moist passion flower later in the day if all went well.

I have to say I was pleasantly surprised to see he was the perfect size for me, not too long and not too short, with just the right girth, just the right size to hit bottom and tickle the door to my womb but not long enough to hurt when he pushes in hard for that final thrust.

He was so hard that the first time I wrapped my hand around his cock and slid from bottom to top, a nice clear drop of precum formed on the tip, I made sure to maintain eye contact as I kissed the tip, slowly sliding my lips over the head, swirling my tongue over the knob, to gather his savory leakage.

He was so turned on, he was shaking from excitement, and I was surprised he lasted as long as he did before unleashing an impressive load. It took me a bit by surprise, as I quickly swallowed to keep from making a mess so we could get going.

As the last drop slid out onto my tongue, I slid off him as I grabbed his hand, pulling him up with me as I stood, pulling his pants and boxers back up, buttoning them quickly, before giving him a sexy smile, as I turned with a glance over my shoulder, an extra wiggle in my hips as I said "Are you ready baby?"

We had a great day together, and before it was over he rocked my world and rang my bell, like no one ever has.

He was so into me, he ate my pussy like it was the best thing he had ever tasted, drunk on my pheromones, making him rock hard seven times, cumming six out of the seven times, giving me so many orgasm, I lost count before the evening came to an end.

Over the next few days we had an amazing time together, the best sex either of us has ever had before I had to say good bye and head back home, wishing I could take him with me.

We kept in touch after I got home from my trip, and had wonderful conversations. We also talked about seeing each other again, as well as sending sexy pictures back and forth, to keep the flame lit and the dream of meeting again alive.

We talked a lot about the amazing intimacy we had together, and even wrote a couple erotic stories for each other. I asked him to write me a story about the things that turn him on the most, and got a very detailed story that concerned me, because it involved roleplay that included impregnation.

I guess because I didn't want any more kids I just dismissed his roleplay fantasy and didn't really know what to do with it, so I just forgot about it and a few months later we lost touch for a while.

He would call once in a while and then disappear for months before I would hear from him again. I had a dream about him one night, and the next morning I was cleaning and found the sexy roleplay story he wrote for me. I decided to read it again.

When I looked at it as purely roleplay fantasy, and remembered the discussion we had about raising kids, and that he definitely didn't want any more little ones at his age. I looked at it differently and after reading the whole thing, I was so turned on I had to get out my vibrator and give myself three good orgasms to calm down.

I started to think about how different he is from anyone else I had dated, and the fact that the time I spent with him was amazing, the way he made me feel loved and respected and never judged, he is one of the few men I have met that just doesn't get angry.

He brought back my faith that there are some decent men left in the world that know how to not only treat a woman right, but also please her in ways she only dreams about. To be kind and gentle, but also know when to grab me by the hair and push me against the wall, yank my panties down to my knees and let out his inner beast, as he has his way with me, reminding me, he is the man in the relationship when I push too far.

I thought back to one of the discussions we had about his relationship, when he was married and why he divorced. I remembered that the downfall of his marriage was from a lack of communication as well as a lack of intimacy, due to not being able to share desires and fantasies with his wife.

On top of that he was a single dad, and didn't date for more than 15 years while he raised his sons.

He has been waiting to meet the right person with communication skills that he trusts, to share his deepest desires and secrets with. Someone that will share his fantasies and rock his world in the bedroom while he is still young enough to get hard and stay hard.

I started putting the pieces in place and realized he liked me enough, and trusted me enough to share his most private fantasies with me, ones he had never shared with anyone else, and he had the time to think about things he would like to try with the right person, and I wanted that right person to be me.

I realized he had given me everything I needed to seduce him, just like he had done to me when we first met, when he made love to me like no one else ever has. I wanted to show him I would do the same for him, it made sense that you treat someone the way you want to be treated, and I sure liked the way he treated me.

I read his sexy story again, and highlighted the different turn-ons described in the story. I found he was pretty easy to excite so I made a mental list and memorized it. I was going to have fun seducing him and making him mine. A simple silky sun dress or accidentally forgetting to wear panties or a bra and letting him discover the missing item of clothing was sure to excite and arouse his desire for me.

Teasing him with little whispered, subtle phrases at just the right time.

"It might be safe enough today to skip the condom and just pull out when you're close so you don't knock me up accidentally. I get so much wetter when I'm close to ovulating, can you feel the difference" or "ok just be careful where you cum baby I think it's pretty risky today."

The big fantasy on his list was giving him the impression that I was not on birth control and slowly giving in to letting him rub his cock against my pussy without a condom at first and then letting just the tip slip inside and going just a little farther in steps until eventually he is deep inside me before I whisper in his ear as he hits bottom.

"You might want to pull out before you cum tonight baby. It might not be the safest time to be deep inside my tight wet unprotected pussy, bareback, rock hard and fully loaded with hot potent sperm."

I decided to test my theory the next time we talked on the phone. In a slow sexy voice I asked him if he remembered when we were together while I was on vacation, the one time he talked me into going bareback for a few strokes, before putting on the condom so he could feel my tight wet pussy, wrapped around his big hard cock knowing I was completely unprotected and close to my ovulation. It made me wet when in his sexy voice he responded "yes".

I asked him if he remembered what he was thinking about when he was deep inside my tight fertile pussy, with the head of his cock leaking and pressed tightly against to opening to my cervix, and he said "yes".

I asked him if he was thinking about how amazing it would feel to take the risk and spray his thick potent sperm, all over my fertile pink pussy, so deep inside, while I was so close to ovulation and possibly knock me up with his baby, and he moaned as he said "Yes".

Then the clincher.

"I said, Michael I want you to be completely honest with me, on a scale from one to ten, how hard is your cock right now?"

There was a slight pause before he softly answered, "eleven".

I actually felt my pussy gush and my nipples get hard when he told me how hard I had made him with just three simple questions. One of the things I have struggled with since we met, was getting him to agree to make plans to meet again.

I know he is busy and trying to improve his business so he can afford to travel so I even offered to fly out to visit him but he shot down the idea and pushed it off to, maybe in the future when things are going smoother.

I remembered in his stories, he mentioned how he got off on subtle hints, like me mentioning I was in a hurry and might have forgotten to wear panties, letting him think about it for a while, before his imagination would get the better of him, and his curiosity would force him to check to see if I was wearing panties.

Seducing him into exploring my sexy curvy body, getting him so turned on he would crave to be deep inside me as soon as we found somewhere semi private. I also remembered how the slightest hint that I was close to ovulation and possibly fertile, mentioning we would have to be "careful" would make him harder than Viagra.

One of the ways he makes me feel special and desired is how easily he gets hard when he touches me. I have never had to, get him hard. He simply kisses me or just touches me, and he is rock hard and ready, to please me.

One of the bonus turn-on's I noticed was how much it turned him on to kiss me after he ate my pussy to orgasm, making sure I could taste myself on his lips.

I had just started a new job and was disappointed we couldn't use my time off, before the new job started to get together and now my next vacation window was three months from now. I was looking at the calendar and thinking about how much I wanted to see him again, when I came up with a great idea. I decided to do a little experiment and sent him a simple note, with a calendar attached, that said.

"Dear Michael, I was hoping we could make plans to see each other on my next break from work, about three months from now, so we have plenty of time to plan and come up with fun things to do while we are together. I have 10 vacation days if you would like to see me again. I attached my schedule for the month I have my vacation time due so we can figure out the best dates to maximize our fun together."

On the calendar I noted my vacation dates and symbols that I knew he would figure out, marking my start and end dates of my monthly period, as well as when I was expected to ovulate.

I know we both were thinking about how amazing it would be to experience the level of intimacy we shared the first time we were together and was excited to see what his reaction would be.

I started to worry a minute after sending the email that he might not still be interested, and figured the suspense would drive me crazy until he responded. I was just starting to consider the" what if's" when I received his email 4 minutes and 20 seconds after receiving mine.

He is not fast at typing and not always quick to respond, so I knew I piqued his interest when he responded so quickly, and when I saw that he had indeed confirmed his desire to see me again. I was so excited I could feel my nipples getting hard.

The last thing I noticed was the dates he selected, and I'm not sure why, but it made me wet to know that he made sure my ovulation day, would happen during my visit.

I knew neither one of us wanted to go beyond roleplaying and actually take a risk of pregnancy so I started to devise a plan that would give him the impression that we were being risky and only I would know for sure that I was safe, no matter what might happen.

I started thinking about how hot it was going to be to roleplay with him, stoking his natural desire to mate and mark me as his, fueling his desire to please me into submission.

I decide to go all in and make it an epic experience for both of us. I made an appointment with my Doctor to get on some type of temporary birth control just for the month of my vacation. While I was there I decided to get the morning after pill and a diaphragm to use as props for the role play.

I could keep up the facade that I was allergic to pharmaceutical birth control and the only type I could use we're condoms or the pull out method.

I could wait until the second or third evening we are together and seduce him onto going bareback "just for a little while so I can feel the heat from his cock without the condom" then when I get him really worked up and close to Cumming.

I can stop and tell him I really want to feel him deep inside my pussy completely unprotected, and to wait a second as I pull his hard cock from my tight wet pussy, and tell him to slide his fingers deep inside and remove my diaphragm. So I can experience what it feels like to be completely unprotected, vulnerable and trusting in him to not cum deep inside my fertile pussy and knock me up, unless I beg him to.

I could wait a couple more nights and show him the morning after pill, tell him this is the only thing protecting me, if we don't use the condoms every time, unless you have enough control and can behave yourself and pull out before you cum in me, every time, without fail baby.

Oh yeah, I was going to enjoy seducing him and making him mine, but the most exciting part, would definitely be chipping away at his will power, with sexy role playing until he just can't control his urges, and my sexy whispered phrases in his ear, push him past the breaking point.

I also figured if we were going to spend more than a week together I might as well take baby steps in seducing him. Making him wear a condom the first couple of times, and after he fills the condom, I take it off, set it aside and, without wiping off the tip of his cock, still dripping sperm, I tease him by rubbing it against my clit until I orgasm, getting a little erratic in my movements and rubbing the slippery tip against my labia first.

Then accidentally lining it up with my tight opening, letting it rest for a moment to see if he pushes in. Making him wear a condom the second time we indulge in penetration for the first few minutes before whispering in his ear.

"Michael, I want to feel you inside me, bare, but I need to be on top, because I don't know if you can resist filling my little pussy with your potent sperm, once you feel my lady lips engulf your engorged knob and slide in to the hilt, feeling the throbbing mushroom head kissing the entrance to my fertile womb."

I could ride him until he cums, sliding forward off his cock just as it starts to pulse and jerk, letting him splash his load all over the inside of my thigs and against my smooth shaved pussy lips as I kiss him passionately.

Letting him think we safely pulled out in time, until he is almost done shooting his load, and I accidentally push back impaling myself on his still hard slippery cock, with an "oops and a giggle" as I take it deep while it still throbs and oozes potent sperm.

Then the first time he pulls out and cums on my tummy, I'll make sure to accidentally move so his sperm puddle runs down towards my still open wet pussy, maybe stop the flow from entering me the first time, blocking it with my fingers, then using my fingertips still dripping his thick slippery sperm to rub my clit and swollen labia as he watches.