Callum and I were talking one day and he brought up how I was exposed in the club getting fingered by Ally.
“You’re a bit of an exhibitionist,” he said.
“I guess I am.”
“Since you like to show off your body, would I be able to show what I have of you to people I know?”
I felt that familiar tingle in my core at the thought of Callum showing someone he knows the dirty pictures and videos I sent him, “yes, you may.”
“It would be really hot if you got pictures and video of you flaunting yourself in public,” Callum suggested, “accidentally flash someone maybe.”
“Oh very accidental,” I smiled. I was getting turned on by the prospect of going out to expose myself and someone catching me. My hand found my pussy to relieve the tension.
“I have a challenge for you,” Callum said, “Go out to a store or the park. Maybe you are doing a chore. Wear something not too obvious but on the shorter side.”
“Am I wearing anything underneath?”
“No. Get video or pictures of yourself flashing and as a bonus try to pick up a much younger bloke or much older one. Under twenty three and over sixty. Bonus points if you have both in one day.”
Callum and I both have older men and women with younger men and women fantasies. Callum really likes the idea of a younger man with a milf. He had experiences with older women when he was younger so I’m sure that shaped his inclination.
A few days later I was thinking about Callum’s challenge. I got excited thinking if I could be so bold. It’s one thing to be daring at a club where there’s drinking and people wanting to get laid but another for being someplace people are going about their daily lives. Still I was up for a challenge.
I looked at my closet to see what would be a good outfit to wear for this mission. I picked out a dress that didn’t look too daring on the hangar. However since I have 38 DDD breasts, it looked a bit more scandalous when I put it on. It was white with a blue flower pattern on it and thin spaghetti straps. The neckline came down low enough to flaunt my cleavage and I could pull it easily if I wanted to expose my large brown areolas and nipples.
It hugged me at my chest but the skirt flowed out a bit more, the hem stopping midway at my thigh. As Callum requested I wore nothing underneath. Though my breasts are quite large they are not hanging down to my knees or even halfway to my belly button. Still it’s obvious when I don’t wear a bra especially when my tits are bouncing as I walk.
My long brown hair I left down but pulled back so a top half was held in a clip the other half was down. Since I was slightly aroused, the evidence could be seen by nipples poking out through the thin cotton material of my dress. Taking a picture of myself in the mirror, I sent it to Callum saying I was going to the grocery store.
The butterflies in my stomach were really going when I pulled in the parking lot of the grocery store. Planning on walking around longer than I needed, I wasn’t really going to get a big order. I grabbed a cart and put my phone down so the screen was facing my chest. Hitting the record button, I began walking in the store.
Looking down, I saw how my breasts jiggled as I moved. The time of day I went was at a slower time so it wasn’t very crowded. I went down an aisle with no one in it. I got the courage to pull down one side of my dress to expose a nipple. At first I did it real quick. After exposing myself the first time it got easier to do it a second time which had my nipple out longer than the first.
I heard someone coming around the corner and though I wasn’t caught, I still felt an embarrassed thrill at that point. Going down another aisle, I got the courage to pull my dress down so that both my breasts were exposed. My pussy was getting wet with me walking around strolling through the store like it was normal. I put my breasts away after a minute and continued my perusal down the aisles.
When I reached the produce section, I went over to the cucumbers. I waited till there wasn’t anyone who would see me to pick up a rather large cucumber. I looked around before pulling my dress down again. Putting the cucumber between my breasts, I snapped a selfie with the hand not keeping the vegetable in place.
To my surprise at the corner of my eye there was an older gentleman who came into view. He stood there shocked. I must have turned red as I righted myself but I did manage the courage to wink at the guy. The older gentleman blushed as well.
Walking by him, I gave him a good morning. He gave me a smile and said, “It’s a good morning now.” When I passed him, I turned around again, gave another smile and reached my arm to the back to lift my skirt up. I gave the old man a few seconds to view my ass.
I began to stroll through an aisle and when the opportunity striked I pulled my dress down again but left it like that for a bit longer. In the pasta aisle I saw the man who I flashed earlier. When he saw me, he smiled and said “hello.”
“Hello,” I responded as an idea popped into my head. “My name’s Sandy.”
“Jim. Nice to meet you Sandy,” his eyes were looking down at my body.
“Could I ask you a favor, Jim?”
“You sure can,” Jim was very enthusiastic.
“I’m taking pictures for a friend and I got a lot of selfies but it would be nice to get full ones. You wouldn’t mind taking some for me?”
“I’d be delighted,” Jim was smiling even bigger than before.
Jim was definitely an older gentleman but he was handsome and looked to be in shape. If I had to guess, I would have guessed he was about sixty two years old.
We walked down the aisle and into another where there was no one in that one. I handed him my phone with the camera ready.
My hands pulled my top down once again to expose my nipples that were even harder than before. I flashed a smile and Jim took a few pictures.
“You’re the best,” I said as I put my breasts away. “Do you mind taking another?”
“Honey, I could do this all day.”
Smiling again, I lifted the front of my dress to expose my fully waxed pussy. I noticed Jim was starting to sport an erection which thrilled me. Another couple came down the aisle so we moved along. We ended up in another aisle where I asked Jim to record from behind.
As he filmed me, I reached behind and lifted my skirt up and held it so my ass could be seen as I walked. In another aisle, I asked him to take a couple more pictures of me. Waiting to be cleared of people again, I turned around and bent down slightly showing my ass. I did it a second time but bent further with my legs spread hoping my pussy would get in the picture.
As I reviewed the pictures Jim took, I was happy to see it was more than just my ass exposed.
“Jim, thank you so much for doing this for me.”
“No thank you. And to think I was annoyed that my wife sent me out to get a couple items.
“I’m sorry to keep you.”
Jim assured me that there was nothing I needed to be forgiven for. I then walked with Jim as he got the last couple things he needed. As we were walking out of the store, I asked Jim if I could thank him for his help.
We went to his car that was close to the front but he drove to another parking lot nearby that was a bit deserted. He parked the car and we both smiled at each other.
I moved to grab the skirt of my dress and lifted it so I could take the whole thing off.
“You are a dream,” Jim said as he reached over and rubbed my breast. My hand found his erection through the fabric of his pants. “You can always call me up to be a photographer.
We started kissing. His hands were all over me. His fingers eventually made their way to my center where he explored my wet hole. Like a hungry man, his mouth was on my breasts.
My hand unzipped his pants letting free a nice sized dick. My hand worked on his cock as he sucked on my nipples. He moved up to my lips to kiss me again. Leaning down to his crotch, I licked the tip before gliding my tongue up and down his shaft.
I swirled my tongue around his tip before I took him into my mouth. A hand caressed his balls as I bobbed my head up and down his shaft. Jim was moaning which spurred on my enthusiasm. He placed a hand on the top of my head. He wasn’t pushing down but had a good grip on my hair. It didn’t take long before Jim was exploding in my mouth. I happily took everything he gave me, swallowing it all down.
We kissed some more. Jim had the biggest grin on his face as he kept telling me how wonderful I was. I asked him to take a picture of me before I put my dress on. Afterwards he drove me back to my car. Before I got out Jim wanted to exchange phone numbers.
Getting back in my car, I sent Callum the pictures that were taken as well as the videos. Callum was excited and he would be able to look at them soon but what he saw was extremely hot.
I was still on a high of what I had done and wasn’t ready to go home. I decided to get a coffee from a cafe. It was later in the morning so the early rush was gone. As I ordered, there was a handsome young man taking my order. He had an all American look with blonde hair and blue eyes. He looked very athletic. He was also tall at six foot two which would tower over my five foot two frame. His eyes were fixated on my breasts. The name tag on his apron said his name was Christian.
I took a seat waiting for my latte to be made. The table was in a corner and could provide some privacy. Callum called me and I popped in my earbuds. I told him how I was nervous at first but massively turned on.
“Have you cum yet today?”
“This morning when I woke up but not since I’ve been out. When I do, I’m going to cum so hard. My pussy is soaking wet.”
As I was saying this, Christian was walking over to hand me my latte. He must have heard what I said because he was bright red. It was quite adorable.
“Here you go, ma’am,” Christian said.
“Thank you,” I smiled.
Callum and I went back to chatting and he said that the young man would probably go home with me if I asked. Ever since I came in, I had wondered what the young man would look like without anything on. I also wondered if he would know what to do with an older woman or need to be tutored.
As Callum and I talked, I felt brazen enough to flash him in the cafe. First I let him have a quick peak then a second time had them out a little longer. Callum on the other end began jacking off. I began to tell him what I would do to him. How I would suck his cock, get it nice and wet and then slip it in between my huge tits so he could titty fuck me.
As I talked dirty to him, I exposed myself again. This time I went to pinch and play with my nipples. I looked behind me and saw Christian coming near. The table next to me had to be cleaned which he was coming over to do. Christian came over and stopped dead in his tracks. Pinching and pulling both nipples, I told Callum I wanted him to cum for me.
“Cum for me. I need cum so bad,” I said as Callum shot a huge load for me. I looked over to Christian who had his mouth open in shock but I only smiled at him. I went back to chatting with Callum and didn’t hurry to fix my dress. Finally I did as Christian walked away dazed.
Callum and I chatted for a few minutes more and he reminded me he challenged me to pick up two men. One older and one younger.
I finished my latte and saw Christian bussing another table.
“Excuse me. My name is Sandy,” I said.
“Christian.”
“I know from your name tag,” I smiled, “how old are you?”
“Eighteen.”
I knew he was young but I thought he was going to say twenty one. Maybe twenty.
I asked him if he was going to go on break soon. Christian said he was actually done in ten minutes.
“No pressure but if you want I can wait for you outside in my car and maybe we can get to know each other.”
“Fuck yeah,” was Christian’s response.
I told him what my car looked like and I’d be waiting. Waiting for him to clock out seemed like the longest ten minutes of my life. I was starting to be uncomfortably aroused.
Finally Christian was knocking on my car window. I unlocked the door and he opened it to sit down.
At first we awkwardly said, “hi.”
“Are you like a porn star or something?”
I laughed and told him I had a friend who put me up to a challenge.
“You playing with your tits telling some guy to cum is the wildest and hottest thing I ever saw.”
I thanked him and we chatted a bit. Christian graduated high school and was going away to college in the fall. He played lacrosse which explained his good physique.
He told me that he found older women very sexy. Christian also said I was the perfect MILF.
“May I touch you?”
I told him that was fine and he reached over to play with my breasts. He pinched and pulled a nipple, making me gasp.
“You like that?”
“Yes.”
I asked if he had a car to which he responded he did. I also asked if he wanted to come over to my house. Again Christian answered in the affirmative. We could have had our fun in the car but I needed a proper fucking. Also I suspected that this eighteen year old could go for multiple rounds.
He went to his car and followed me to my house. As soon as we got in the house, Christian was all over me. I took him to the bedroom where I promptly removed my dress. Christian pulled me in a tight embrace to kiss me again.
He then turned me around and had me on my knees by the edge of the bed. Bending over my ass was up. He gave me a smack to my ass before diving his head into my pussy.
Christian may have been young but he had skills. His tongue explored my wet pussy lapping up my juices. I was moaning as he worked on me. He then licked his tongue up to my asshole where he enthusiastically rimmed me.
First he used both hands to spread my ass cheeks wide. Then he moved one in front to play with my clit.
“Oh fuck. Yes. Lick my asshole. Fuck. You’re so good,” I was saying a string of praises as my orgasm built. I exploded and still Christian didn’t let up on his attack on my ass and clit. I was screaming louder as another orgasm hit me.
“Oh, shiiit,” I screamed.
The young man came up for breath and I turned around to kiss him wildly.
“I want to explore your body,” I told him.
Christian undressed for me. Seeing his strong body kept my arousal at a heightened state. When he revealed his cock, I was given quite the happy surprise. The boy was hung. Not only was it long but the thickness was what was most impressive. He had one of the largest, if not the largest, cock I ever saw in person.
“Holy shit. Are you sure you’re not a porn star?” We both laughed.
I laid him down. At first my hands slowly traced every inch of his body. I didn’t touch his dick yet, wanting to tease him for a bit. I kissed and licked up and down his body. When I was going back down again. I kissed and licked all around his crotch. Finally I took his monster cock in my hand, looking up at Christian I gave it one long lick from the shaft to the tip where I swirled my tongue around his head.
I spit on his dick a couple times making sure it got nice and wet. My hand began jacking him off slowly as I licked his shaved balls. I licked up again, stopping midway to spit on it again. When I reached the head, I took it in my mouth. At first I only had the head in while one hand jerked him off and the other cupped his balls.
Christian seemed to enjoy what I was doing. Since he was so big there was no way I was going to deepthroat him in this position. However I made a good effort to get as much of him in my mouth as I could. I made sure spit ran down to keep what I was jacking off still wet.
Christian was moaning in a way I knew he was close. Faster I worked on his cock until Christian growled out his pleasure and a massive amount of cum poured into my mouth.
I waited for his orgasm to subside before I came up to give him a kiss.
“Fuck that was amazing,” Christian said.
We chatted for a bit and Christian gave me a nice massage as we did. I found out I wasn’t the first older woman he was with. His mom’s best friend had taught him everything he knew. his mom and her friend was only a year older than me.
It wasn’t long before Christian was hard again. Christian began kissing me at my lower back and worked his way up to kiss the back of my neck. To feel his powerful body on me energized my arousal. Turning my head back a little, Christian and I shared a very sensual kiss.
He told me he wanted me to ride his face, which I was happy to do. He laid down and I straddled his face. His tongue was magic on my pussy. I grinded into him until I came all over his face.
I let him up for air and told him I need his big dick in me. Laying on my back, Christian moved in between my legs. I lined him up with my entrance anticipating how he would stretch me.
It didn’t take long for his dick to stretch me in a way that was euphoric. He slowly moved inch by inch letting me get used to his girth.
“Oh fuck your stretching me,” I said before pulling him down in a kiss. As our tongues danced with each other, he continued to enter himself into me until he reached the hilt.
“Fuck me how you want. I want to make your dick feel good.”
Christian started moving faster in me. It hit every part of me inside, driving me wild.
“Fuck use this pussy. Don’t go easy on me, baby,” I was a woman possessed by the pleasure he gave my body. He showed me no mercy. Him hitting every part of me from inside was making me scream in ecstasy. He took my legs and pushed them all the way back so my feet were over my head. This position hit me even harder causing me to cum. He kept pounding at me even when I was squirting my release.
“Fuck, you’re a squirter,” Christian said when he noticed how wet it was getting.
“Yes. Fuck. You make my pussy feel so good.”
Christian moved so he was on his back and I was on top. I fixed myself so I was up right. Riding his dick fast, he grabbed at my tits as they bounced up and down.
He moved up to meet my thrusts as well.
“Fuck your tits are fantastic. Fucking ride this dick.”
Christian sat up for his mouth to take a nipple in his mouth as he sucked and nibbled on it. His dick was stretching me in a way I hadn’t been in a long time.
“Oh shit, I’m going to cum again,” Christian moved his hand between us to play with my clit.
“Are you going to squirt all over my big dick again?”
“Yes. Yes I love it,” I shouted.
After a few thrusts again I was cumming all over him. He again moved us so I was on my back and he was on top.
“This pussy is too good.”
“You can cum in me. I want your cum in me,” I kept begging for his cum.
He lasted a couple minutes later but finally I was rewarded with his cum. Afterwards I felt truly satisfied and I believe Christian felt the same.
Christian and I ended up in the shower where he once again got hard. He had me bent over in my shower. That position really destroyed my pussy with how deep it went but I loved every second of it. Again the virile young man exploded inside me.
I only had a robe on afterwards while he only put his boxers on. I ordered a pizza and we watched some TV together. We fucked three more times that night. Also we went down on each other again. Christian was very orally inclined.
He ended up leaving in the morning. Christian told me he would love to see me again and hinted he wouldn’t mind me partying with him and a couple of buddies of his.
I told him I would definitely be up for that. I didn’t tell Callum all the details about my adventure with the young man right away. I needed a break from all the heavy duty sex I had. When I did get around telling Callum about it we ended up having one of the hottest mutual masturbation sessions we ever had.
I thanked Callum for challenging me and opening me up to new experiences. I wondered what else my long distance friend could challenge me to do.