43 FIRST PLACE GRACE 44 FRISKY N RISKY
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A Series Of Risky Events free porn video
I'm a little in disbelief today. I read the Snapchat message a dozen times, each time thinking it can't be right. How? How could it be real, I was having the time of my life. As a recently divorced man, I was just starting to live after years in a dead bedroom. The ride, as short as it was, was a beautiful and amazing roller coaster. The exhilaration and youth I felt while pleasuring these women will be something I always remember fondly.
Last September I decided to get a vasectomy. I already have two great kids in their teens, and my wife and I didn't want anymore. Flash forward to January, my wife surprises me with a divorce. I understood her reasoning, and I respected her wishes.
We parted ways and we split custody of the children 50/50. At 45 I realized I had not been single since I was 21. I was nervous to get back in the dating game, unsure of myself, and if I was desirable. My views on my age and if I would be desired all changed, and changed quickly. I was unsure of where to start over at, online dating was never a thing when I was younger.
With some reluctance and a bit of coaxing from a friend, I signed up for Tinder. The options and selection for men over 40, hell 30, is very limited. It’s filled with women divorced multiple times or women with multiple young children. I wanted stability, what I found was instability and a lot of fun.
Since February I've had sex with four different women. It could have been much more I believe, but I prefer quality over quantity. I use Tinder to find these women, and a fake Snapchat to communicate. All meetings took place at a hotel, a room I paid for with a Visa Gift card for the exact amount of the room. None of these women know my name, my occupation, or where I live. I’m a secret to these women, and that is how I prefer it.
My biggest secret though is all these women's age range. Not one of these girls is over the age of 21, the youngest was 18 and a senior in High School. I paid none of these women a dime, none of them wanted anything in return but companionship. I was shocked to see how many younger women I was able to communicate with.
Sure I had the ones who ignored me, the ones who talked a bit then ghosted. But, I was able to find young women who desired an older, experienced man like myself. A man who is not a stud, but would give them the sex they craved. Most importantly, they found someone who was upfront and honest of his wants, without all the fuck-boy qualities attached to men their age.
The first woman was Michelle. She is a 20-year-old Latina mix with a child. She was a single mom who just needed to get away, even for one night. We matched, talked, and met within the first week. I took her to a nice restaurant where she was treated to whatever her heart desired. We had a good conversation and laughed all night. It was pleasant to have such an enriching conversation with a young woman. Before dinner was through she asked what else I had planned that night. I was still in disbelief a beautiful young woman would want to go out to dinner. I remember fondly, tilting her head, smiling at me with her bright red lipstick, and asking me if I wanted to get a room.
Within an hour of paying the check, we rushed to find a hotel. We were barely able to get through the door before she was all over me. Our kissing, our touching, our bodies getting acquainted.
Michelle was the first woman to suck my cock since high school. My wife never cared too, it hurt her jaw. Michelle spared nothing, giving me her best effort. Her throat took my cock to its base, my almost eight-inch cock filling her mouth. She almost got me to cum, but I made her stop.
Instead, I wanted to pleasure her. I stripped her out of her red dress that matched her lipstick. Had her lay on the bed in her underwear, matching of course. I peeled her panties off with my teeth, revealing a perfectly shaved pussy. Her lips so tight I swear it took two hands to separate. Her taste, oh her taste. She tasted of youth and sweetness. My tongue pleasured her pussy, I licked her for what felt like an hour.
Finally, she urged me up to her, our lips locking. My body on top of hers, my erect cock close to her pussy. With no talking and just kissing she reaches below, handling my cock like it's delicate. She places it at her pussy and allows me to enter her. I'm slow with her, gentle almost. My ex-wife never liked it rough, but Michelle wants to get fucked, not make love.
I'd be lying if I said my mind was in the right. I was in heaven thinking how good she felt, how young she was, and how perfect the night was. Michelle's legs were spread do wide and I was able to fuck her deep. I lasted maybe ten minutes before I could feel the cum trickle out of me, no control over my cock as it shot cum inside Michelle. As if in unison we both let out moans of pleasure as we came in unison, our juices mixed.
“I wasn't planning on that,” Michelle said softly as I lay on top of her, still inside of her. “We’ll have to get Plan B before I go home.”
“That won’t be necessary, I had a vasectomy last fall,” I reassured her, still laying on her and inside of her. I can not bring myself to leave her, it was the best sex I had in almost two decades.
“Oh perfect!” she said excitedly.
We spent the rest of the evening in that hotel room, having sex a total of three times. Each time filled with passion and raw emotion. With every load I left inside her pussy, I felt close with her, as if we were connected that night. No talks of any expectations going forward except pleasure.
Michelle and I met a total of four times, each time going similar to the first. She ended up rekindling things with her child’s father and got off Tinder. We deleted each other off Snapchat to respect her relationship. We haven't talked since.
The second woman was Olivia, a sexy sophomore at the local community college. She was twenty and had a wild side to her. She messaged me on a Thursday night asking if I was real because she hadn’t seen many old guys on Tinder.
Olivia was out with friends drinking, but bored. We talked for an hour on Tinder before she gave me her Snap Chat. I had told her my life story in that hour, the divorce, being single, and unsure of what I was looking for.
The fist Snapchat she sends me is from a bathroom. She had her tank top pulled up covering half her face, exposing her small B cup breasts with freckles covering.
She got right to what she desired after that. Olivia talked about how she prefers older men, but I was the oldest thus far she has talked too. She was very upfront and forward, which is a quality I like in anyone. Olivia wanted to meet up for sex but couldn't host. I offered a hotel room if she was serious. She said she could meet in an hour at a hotel off the main strip of town.
I got to the hotel a little early and waited in the parking lot. I was not going to buy a room until I knew she was serious, I had a few flake out in the past. Olivia’s white Chevy Cruz pulls into the lot, and she notices me right away. She gets out of her car and she looks stunning.
Olivia is a shorter girl, no more than 5”2, she is super skinny with a small ass and tits. She has long blonde hair that touches the mid part of her back. As if we had been friends for a year, Olivia walks to me and hugs me, kissing me on the cheek. We walk together holding hands into the lobby of the hotel where I get us a room.
We get into the room and Olivia stips nude immediately.
“How about a shower?” she asks, as her shorts hit the floor. Her body is flawless. She has abs peeking through her stomach, not the in-shape, but naturally skinny abs. Her breasts are so petite and lovely.
“That sounds perfect,” I tell her, as I move close to her, hugging again.
I run my hands on her back to her butt. I grab hold of a cheek and squeeze. Her whole cheek fits in my hand is the softness of her youthful skin gives me an instant erection.
I strip and head to the shower where Olivia already is. In the shower, we wash each other. Not sparing an inch, I clean her intimately. Without even realizing it I am starting to dictate that I clean her. She seems to like it. I have her spread her ass apart, as I use my hand and soap to give her a deep clean. I have her gently wash my cock, she seems enthralled by my dick as she washes my balls. I shut the water off and dry her off.
“Let’s head to the bed,” I tell her after we are both dry. Olivia walks to the main room of the hotel, to her purse.
“Fuck, I thought I had a condom in here,” she says with a sad tone of voice. “I’m not on birth control, it fucks with my hormones.”
I walk up to her as she keeps looking as if the condom will appear if she keeps looking. “It’s okay, I had a vasectomy last year, but if you need me to where one I can find a gas station.”
I kiss her neck as she keeps looking.
Turning around and hugging me she looks up at me. “So you're for sure shooting blanks?”
“Yes, hun,” I reassure her.
We move to one of the two queen beds in the room. I lay her down on her back and spread her legs wide. I gave Michelle oral every time we met, so I have developed a taste for it. With her legs spread, I begin to lick Olivia. She has a little bit of hair as if she hasn’t shaved in a week or so. It prickles my face as I lick, but I don’t mind. Her pussy lips look asymmetrical, with one of her inner lips longer than the other.
Olivia is so petite that I lift her legs right off the bed holding them in the air. Her petite ass right in front of me. I lick her entire crack, beginning to end. Tasting every inch that I just washed.
“I need that cock.” she moans out as I pleasure her, licking her most intimate areas.
Olivia rolls over onto her stomach. Her small ass was visible, wet with my saliva and her juices. I move on top of her and begin to grind my cock on her ass. Kissing her neck and upper back as I do so.
Without telling her I slide inside of her. Her small frame allows me to use her as I want, and with very little ass to stop me, I go deep. I start fucking hard and never stop. Fucking her on her stomach feels wat too good, her pussy is tight and like a velvet glove. As I thrust in her I warn her how close I am to cumming. With her face buried in the comforter to hide her moans, she raises her head.
“Finish in me, I’ve never had that!”
That one sentence instantly puts me over the edge. I believe her, she wanted a condom until I told her I was fixed. I’m about to breed this young pussy for the first time. I thrust harder, faster until I release inside of her. Wave after wave of cum is pushed inside of her as my cock pulses.
“Here,” she says, handing me her phone. “Film my pussy as you pull out, I wanna see what it looks like.”
As I slowly pull out my cock, the base has my cum on it, thick and white. Her pussy at first looks just wet, like before.
“Get in doggy position,” I ask her.
Doing as she was told, Olivia gets in position. Gravity and time take over and the first bit of cum begins to exit her vagina. The cum is thick and flows downward on her pussy, almost reaching her clit before it falls on the bed below. I shot a big load in her, and the video turns out amazing.
“So, what does it feel like?” I ask out of curiosity. I lay on the bed on my back, and Olivia lays in my arms.
“I couldn't feel you cumming in me, but now it feels much wetter than I normally feel,” she says laughing.
Olivia and I fucked once more an hour later, then she left to head back to her apartment. We got along splendid and vibed well, so I'm unsure of why she ended up disappearing. We never spoke again after that night.
My third encounter was the quickest meeting. It was late on a weeknight when my phone vibrated. I almost didn’t look because I was close to going to bed for the night. I saw a Tinder message from Vanessa, a twenty-one year old bartender.
“Hey, you looking for anything fun tonight? I’m done with work in 30.” she messaged me.
We talked for about fifteen minutes. She was into older guys and wanted a quick fuck before heading home. She was close to forty minutes away, so I could not host. She did not want to host but knew a secluded spot we could meet. I type in the location and head out to meet. There are no cars on the road, and travel is quick and easy. During my drive, I keep looking at Vanessa’s photos. She is a voluptuous woman, curves in all the right areas.
I get to the destination, it’s a boat launch by the river, about a half-mile off the roadway. There is only one road in and out. I drive around a corner and see an older style Toyota Camry parked in the grass. A woman inside with the interior light on. She waves at me as I park my car. Vanessa quickly gets out of her car and walks to my driver's window. She leans in close to me, I can smell restaurant on her, as well as perfume.
“You're real,” I joke with her. “You look very pretty.” I compliment her.
My confidence is growing after meeting two younger women so far.
She shows me a fantastic smile. “Thanks! So their room for two in the back?”
I step out of the car and we both get in the back seat. There is little talk once in the back. Vanessa crawls on top of me and we kiss. Her tongue is pierced, and I feel it hit my tongue as we makeout.
Vanessa takes off her shirt, showing off a cute purple bra. Her breasts are pushed up high on her chest. She grinds on my erect cock, grinding through two layers of clothing. I’m horny, and it’s late.
“Let’s fuck,” I say to her.
Vanessa reaches into her purse pulling out a condom. I strip out of my pants, leaving my shirt on. Vanessa strips, leaving her bra on. She bends down taking my cock in her mouth while opening the condom. and places it on my shaft. Immediately she gets on top of me and begins to ride me in the backseat of the car.
Her moans are loud in the vehicle, almost echoing off the interior. Vanessa is doing all the work, she is using her hips to pleasure herself. It feels amazing, and knowing that Vanessa is using my cock as her toy, makes it even better.
With the condom on, I am lasting much longer than normal. The sensation is not as strong as when I fuck raw. Vanessa continues to ride me, grinding her hips.
“Put a finger in my ass,” she calls out unexpectedly.
I take my index finger and put it in her mouth touching her cheek. Her saliva is slippery, and I want her to spit to lube her ass. She sucks on my finger hard, as if it is a cock. I take my finger out and move my finger to her ass. I feel her tight asshole and with a bit of force, it slides inside her. I push it in to the last knuckle. She is tight and the spit does little to help. As she continues to grind on me she is fucking herself with my finger.
Her grinding get’s me in a good groove, I can feel I will cum soon. A finger in her ass and her pussy is wet, my cock can not handle much more. I feel my cock release inside of her, she continues to grind. We both cum at the same time.
She stays on me a few moments after we cum, I feel an unusual feeling. Something is dripping down my leg. I move Vanessa off me and look down. The condom broke, I filled her up by mistake. Vanessa sees this too but does not seem to give a shit.
We both got dressed and resituated. A long hug and a kiss on the cheek goodbye before we parted ways. We met two more times at that boat launch, the last two she took me raw, letting me fill her up.
The final woman I met was by far my favorite. I messaged Lauren and didn’t get a response for two weeks. Her profile said she was eighteen and close to graduating high school. I messaged a lot of eighteen year old’s as a slim hope. I never expected one to chat or meet.
After two weeks passed Lauren messaged me. She sounded young, just like an inexperienced girl. She was held back in 8th grade, and was almost nineteen and still in high school. My brain, though, could not get over her being legal and especially in high school. I needed her, and I wanted to know I fucked a high school girl. A girl only three years older than my daughter turned me on.
Lauren and I talked for almost a month before we met. She would always want to talk, which is difficult with me working a lot. I've noticed the younger women tend to text and chat all day, probably the only flaw of the young. I offered many times to meet up and hangout. Each time an excuse was made by Lauren. I was beginning to think she would never want to meet and almost ended things. I am very glad I didn't.
Lauren went to a small high school, a graduating class of 90. She claimed she was a virgin and wanted to lose her virginity before going off to university. She was reluctant to be with a guy from school and didn’t want rumors spread. Finally after weeks of talking, she agreed to meet up.
Lauren and I went to a museum the first time we met. The time spent together was rewarding, and Lauren was so innocent and cute. She had a beautiful body that was hidden by oversized clothing. Her red hair was natural, and curled. I could tell she was nervous the first meeting, so I didn’t push anything. I was genuinely having a good time with her. We parted ways after the museum. As we broke our hug, Lauren stood on her tiptoes to give me a kiss on my cheek. From that moment on, I was hooked.
Two weeks later we are out to a nice dinner. I took her to a local one I frequent downtown. It was her first experience with Thai food, and she enjoyed it. We held hands, flirted, and enjoyed the company of one another. We parted ways after dinner. Another hug with another kiss, this time lips to lip. Just a peck, if you could call it that, but it was progressing.
I was unsure If I wanted to meet a third time. I was starting to second guess myself. I did not want to mess with an eighteen-year-old girl's head. I was worried she was catching feelings for me, which was not what I wanted or needed. I would never date a younger woman, but absolutely fuck one.
But, Lauren kept talking to me and I would try to distance myself. One night though, she brought up sex, and thinking she was ready to lose her virginity. We talked of how sex should go and be, we spoke of how she would occasionally watch porn. Lauren wanted sex, and asked if I would be ok with being with her. I thought long and hard about it, and I could not pass the opportunity to take a young woman’s virginity. I was in.
The night of the fuck, I took Lauren to dinner. As usual, we had a great time and enjoyed each other's company. I had asked Lauren to wear a nice dress, I was tired of the baggy clothes.
Lauren showed up in a flower dress that flowed to her knees. Showing just a bit of chest to keep anyone interested. During dinner, she sat near me at a small tow top table. Occasionally she would rest her hand on my thigh. She was flirting hard that night, some newfound confidence. Our conversations were deep, and our connection evident. That night, nothing else mattered but Lauren. Eventually, dinner would come to an end and a decision would need to be made.
I took Lauren by the hand and needed to know. “So, do you still feel ready tonight?”
Without any hesitation and with a mature tone, “Absolutely, I am ready.” Lauren looked poised and beautiful that evening.
“My parents have gone to the cottage up north, we could go to my house,” she said, shocking me.
The easy and logical thing would have been to still get a hotel, but a new desire crept in my head. I could fuck Lauren in her bed at her house. Again, I should have chosen the hotel, but ultimately her home was decided on.
The drive to her house was quiet. With the radio on low and little conversation. Her house is situated on a side street off of a major business route. It’s a small family home with green shutters on a white siding. A small driveway leads to a detached garage in the rear of the house. On the front by the wooden door is a sign “Marzalino’s”.
Lauren has me park in the driveway and led me on a small path to the rear of the house. Lauren unlocked the deadbolt and opens the door. I follow her as she enters first, a overhead light turns on, lighting up the kitchen. The fridge has pictures of Laren and who I assume to be her parents.
“Wanna head upstairs, or look at pictures all night?” she says a sly tone.
She leads us upstairs to her room, second room on the left down a long hallway. It’s a simple room, painted blue with white clouds. There is a twin bed, a nightstand, and a desk, the closet is off near the window that faces out to the road we pulled it off.
I move closer to Lauren, holding her from behind. I kiss her neck softly, smelling how wonderful she is. Her curly red hair smells of lilacs. I bend down slightly as my hands find her knee’s, I carefully run my hand up her legs, lifting her dress. Lifting up her dress I reveal some red cotton panties. Her skin is pale, but soft to the touch.
I turn Lauren round to face me, we stand close to one another. I grab hold of her wrist and gently move them to my pants. She fuss’s with my belt, and then pull’s my pants to the ground. She stares at me in my boxers, my erection obvious. It’s only a few seconds before she removes my boxer’s on her own. My erect cock now visible to Lauren, she looks at my cock for a moment before realizing she is staring. I grab hold of her hand and have her massage my cock. She jerk’s it back and forth quickly, I help her slow down and find a good pace.
“Lay on the bed,” I order her.
She releases my cock from her hand and lays on the bed. I move her leg’s apart and slide my head under her dress. My nose finds her crotch where I inhale her aroma. I bury my nose right in her pussy, her panties doing little to hinder my nose. I slide a hand underneath her dress to move her panties to the side. My tongue meets her clitoris immediately, her taste overwhelmed my taste buds, sending signals to my brain.
Lauren is squirming around as I pleasure her pussy for the first time, her first time having a man’s tongue pleasure her. I peek my head out from her dress for a split second.
“First time being eaten out?” I ask her.
With an intentional roll of her eyes, “Duh!” she sarcastically says.
I order her out of her dress. Lauren stood up and unzipped her backing of the dress. The dress fell to the floor, with no bra, and panties still on her. I graciously help her out of those, so now she stands completely nude on me. I move to the bed, bringing her with me. I lay down on my back and motioned her over.
I have Lauren lay overtop of me, with her pussy and ass in my face. Lauren starts to jerk me off again, not even thinking of sucking my cock. I begin to lick Lauren again, this time finding her hairless asshole. My tongue pleasures both holes equally. Lauren’s jerking off my cock is starting to hurt, so I move her off of me.
As she lays on her back I move in quickly on her. I lay over her and we begin kissing. I take my cock and place it on the outside of her pussy. I take my time teasing her, going slowly. I push the head of my cock in her, and she lets out a moan. I keep moving my head in and out of her, slowly increasing how deep I go. Lauren’s virgin pussy is tight and is putting up resistance.
It’s not long before I am almost fucking her to the base of my cock, I continue to move slow but her body is opening up and adjusting. Lauren’s moans are intensifying, she’s quiet as I leave her, but moans loudly as I push my cock inside her.
Lauren's youthful wetness helped, as did the precum that is oozing into her. I come close to cumming three times, but I edge myself and successfully not give in to temptation. The fourth time, however, I could not contain myself. Lauren’s pussy was hugging my shaft tightly, wanting to be bred. I could feel the orgasm coming from a long way. I felt myself start to leak cum into her, followed by an intense orgasm. My cum floods her inner pussy and I release everything into her.
Without thinking or any pre-planning, I leave Lauren right when I finish cumming. I move down and place my face between her legs. My tongue meet’s her labia, as I begin to give her oral again, and I taste myself for the first time, not caring as I would have in the past. The cum is thick, like mucus, but it isn’t awful.
Once I feel I have a good amount, I move up to Lauren and we kiss. My tongue and her’s meet as she tastes semen for the first time. If it grossed her out, she did a great job hiding it.
Tired, we spoon together and fall asleep. We awake in the morning, just after 8. I rub her back, lightly, using my nails. As I rub her back, I work to her butt and run my finger down her crack. I find her pussy and begin rubbing her, she moves her legs slightly to open herself up.
I finger her with one finger, then two, within a few minutes I have three in her. Lauren moves to her stomach where I lay on her. I push my cock in her once more, going to my base. She takes it well, no discomfort.
Our bodies turn red as my crotch pounds her. I don’t last long and I don’t try to fight it. I cum in her a second time, keeping the base of my cock buried in her, releasing as far in her as I can. This load stays in her a while because we fall back asleep together.
Things went so well with Lauren that we continued to see each other. For six weeks we met up. I would get a hotel room, she would lie and say she was going to a friends. We would stay the night, fucking till the early morning. Lauren’s skill grew as did her confidence. Lauren was turning into a great lover.
I was excited today when she texted me, as I really wanted to see her again. The message I received was shocking.
Lauren was pregnant, she found out she is very early on. Before getting a scheduled MRI she had her urine looked at. They found her to be pregnant, and by the sounds of what the Dr said, she got pregnant that first night.
Apparently, vasectomies are not a guarantee. I feel bad I did this to Lauren, but I also feel for the other women. The ones I fucked raw and came in. I have no way to ask if they are okay, or how things are. I would hate to know I knocked up some of the others. I’m not entirely sure of what I will do with Lauren, another kid is not in my future but I also can not abandon her. I suppose some alcohol and a few good nights of sleep are in order before I make a decision.
Valentina
- 05.11.2021
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