I guess I should start from the beginning. Jon and I had been together for a while. Life was good. He treated me well and I loved him. One day we started talking about our exs. I learned that he had a pretty wild relationship before me. He is older than me. I am 23, he is 29, so I knew he’d had previous relationships. I just didn’t realize how wild the sex with this ex was.
We had a great sex life, but nothing like he described. I’d only had one other partner before him. I mean, I’m pretty. At 5' nothing and 100 lbs, I get a lot of attention and I love it, but I never acted on it.
As we talked about fantasies I admitted I had a thing for older men. He asked if that’s why I chose him and I admitted that was part of it. Then he asked me how old. I told him there were guys in their 40s and 50s at work that I was attracted to. He pressed me on how attracted. I finally admitted I fantasized about them sometimes.
I thought he’d be weird about it. Instead he got all excited and told me that was hot. Next thing I knew we were fucking like rabbits with him asking me about the older guys and what I imagined doing with them. It was wild intense sex and I came like crazy.
A few days later we started talking about fantasies again. I asked him why he liked the fact I was into older men so much. He told me he had a fantasy of seeing me with another man and the idea of it being an older man was even more exciting.
At first I thought it was an odd fantasy, but I loved him and since it was just fantasy, I thought I’d indulge it. I asked him more about it. He started showing me stories online about women with other men. They were from a man’s perspective. They talked about how much they enjoyed seeing their wives or GFs with another man. Even doing things with the other man she would not do with him.
As we read the stories I admit I got turned on. I could picture me and some of the older men I knew. I could picture letting them take me in front of my boyfriend. We started incorporating this into our sex. I admit having sex with my boyfriend describing how I’d look with another cock in me, or how he’d like to watch me, made sex much more intense.
One day he suggested we try to make the fantasy real. Real? No way, I thought. I had excuses. Who would we get? How would we choose him? I would never do it with someone I knew.
What I realized was, I was turned on by the idea but the logistics bothered me. My boyfriend suggested we try craigslist and see what we found. At worst we’d get some laughs out of it. I agreed.
He placed the ad. We did not have to wait long. We got tons of responses. A lot of one liners. A lot of cock pictures. I let my boyfriend weed through them. Eventually he found a few that stood out. I did not read them but he starting corresponding.
One of the guys really piqued my boyfriends interest. He started writing erotic stories. I would have thought he just copied them from somewhere except they were kind of specific to us. Jon (my boyfriend) would show me the stories and I would read them aloud to him.
Not everything in the stories turned me on, but I have to admit reading them, knowing someone had written them for us, and describing situations we fantasized about was a turn on. The story reading always led to great sex.
Jon mentioned he was going to start calling some of the guys he picked out. I did not want to look to interested. The idea of making it a reality both frightened me and turned me on. Jon did not push it. Jon asked if there was a picture he could send out.
I found one that was fully dressed but really showed off my figure. With the face cropped out, I told him he could send it. The idea that he wanted to show me off to strangers was a turn on. I wondered what they thought.
One day Jon brought up the guy who wrote the stories. It turns out Jon had talked to him on the phone and thought he sounded perfect. I was skeptical. Jon started by showing me pictures. He was not gorgeous but he was certainly attractive.
Jon told me how much the guy liked my pictures. It made me feel good to know he thought I was hot. Then Jon and I started discussing the stories. Jon asked me what I liked and didn’t like about the stories.
In talking about the stories I could see me in parts of them. It also made me think about the man who wrote them. This guy obviously understood that sex was not just slam me on a mattress. His stories showed engagement, thought, and included me and Jon. I started wondering what this man would be like in person.
Jon would tell me about his interactions with the man. It became clear this was the guy Jon thought would work. He sounded nice, I liked his stories, but I did not know what the next step was. I certainly wasn’t ready to fuck this guy.
A few days later Jon asked me if he could take a picture of me to send the guy. I told Jon to send one of the pics he has. Jon said the guy had asked for a candid shot. Here it comes I thought. The guy wants naked pics, but no, Jon said he just wanted pics that were taken just for him. In fact he said he didn’t want anything x or r rated.
I thought about what I was wearing. I was in a pair of tight shorts and a T shirt. What the hell. I let Jon take the pic. Almost immediately the guy responded. He thanked both of us for the picture and said how pretty I was. He hoped he’d get a chance to meet us. I was flattered by the compliments. After all, it’s nice to be admired. I smiled at Jon and Jon joked that the man had great taste.
A few days passed and Jon asked if could take another picture. I thought about the first one. I liked the compliments. I kind of liked the idea of being shown off. I said sure but told Jon to wait a minute. I went to change.
From the letters and the stories I knew what this guy liked. Short flirty skirts. Lacy tops. Cute shorts or jeans with a top that showed a of leg and a lot of belly. Well I had plenty of clothes like that. I also knew he liked cute lacy thongs and boy shorts. Well, I knew that wasn’t going to Happen. I also realized if I went through with this eventually he’d see a lot more. The thought kind of excited me.
I went to my closet and found a cute short sundress. The dress covered me so I skipped the bra. I looked in the mirror. I looked pretty, not sexy, not slutty, but pretty. For fun I messed up my hair a bit. Now I looked like the girl next door who just did something naughty. Perfect I thought.
I went out and showed Jon. I did a little spin.
He said, “Wow, you look great.”
I liked the compliment.
Jon said “I can’t wait to show Dave what a hot girlfriend I have.”
The thought of Jon getting excited by showing me off was really turning me on. I wondered if Dave would like the pictures. I realized that I really wanted him too.
Jon started taking pics and I started posing. Hand on hip, turn around look over my shoulder. That kind of thing. In one I let the shoulder strap of the dress slide down my arm a bit and showed off a little of the top of my tits. On another I held my leg out and pulled the hem of my dress up to show off my entire leg and hip stopping just short of my panties on my hips.
Jon was encouraging me. Telling me how sexy I was. Telling me what a naughty girl I was taking pictures for man I’d never met. It was all turning me on. We sat down and went through the pictures. We sent Dave 5. We got a response almost right away.
He started off telling me how sexy I looked and how lucky Jon was. Then he went to each picture and told us what he liked best. He liked that I wanted to take pics and show off for him. He said he also liked my naughty side.
All this was too much. I unzipped Jon’s pants, straddled his cock. Pulled my thong aside and just started fucking him. Jon started talking to me.
“So you liked showing off for Dave. I bet you’d like to show him how naughty, even slutty you can misbehave.”
He told me that Dave had sent him a cock pic and that Dave was big and thick. He kept on telling me how much he’d like to see that big cock split my pussy. I could see it in my head. Fucking Dave, feeling full, watching Jon. I Came. A great orgasm. So wet I had to throw both the panties and the dress into the wash. Next day when Jon was at worked I sneaked a peak at his email and found the picture of Dave’s cock. It would definitely fill me up.
One day I was putting on a cute thong. As I did I asked Jon if he thought Dave would like them.
Jon responded with, “Let’s see.”
He took a few pics from the waist down of me in my thong from the back and front.
Again the response was quick. Dave said he loved the thong. He complimented my ass and my legs. This time a bit more forward. He said he wanted to rip the thong off me and for me to wrap my legs around him while he fucked me silly.
He said he could picture me on my knees, face down on the bed, ass in the air, the thong pulled down over my ass but still wrapped around my thighs and him plunging his cock in me from behind. Both those images went through my mind. They both made me tingle. I could see that as I read the responses out loud Jon was getting hard too.
After that we took pics every few days. It definitely turned us on seeing the responses. I would show off my dresses. I would sometimes pull them up to show off the panties I was wearing. One time I took pictures in just a wife beater and a thong. In a couple I was pantiless in a dress. I would pull the dress up to show off my naked ass.
Taking the pics turned me on. Knowing I was turning on this stranger and Jon was a win win. Jon and I fucked almost every day. He would tell me what a sexy slut I was. I was loving it when he said it. He would say he couldn’t wait to see me give away my tight little pussy. I told him if he was good I might let him watch when I do.
The weekend was coming up. We had no plans Saturday. Out of the blue Jon said, “Let’s meet Dave.”
My stomach fluttered. This is the guy we’d been fantasizing about. This is the guy I’d been showing off too. He’s the guy that owned that big cock.
I knew I should say no, but I said, “OK.”
That night Jon and I fucked like never before. He kept telling me what a slut I was for even considering meeting this man. Telling me how he wanted to watch me get fucked. How he wanted to see my lips wrapped around that big cock. All those images were going through my head and I was loving them.
Saturday came and I was like a schoolgirl on a first date. I was pretty sure nothing would happen our first meeting, but still. I was looking for something to wear. I picked out a pink and purple lacy thong. One of Jon’s favorites.
Jon came in the room and said, “I bet Dave will love those.”
I thought about Dave seeing them. I put them on. I wasn’t sure on a bra.
Jon chimed in, “Don’t wear a bra. I want him to see those sexy tits.”
I realized I wanted him to see them too.
I pulled on a short skirt. It stopped an inch below my ass. It was loose so it flounced when I walked. For a top I picked out a short sleeve v necked pullover. It was loose enough that if I leaned forward you could see my tits.
Jon grabbed me, kissed me, and told me I looked hot. He said he couldn’t wait to be out with me and show me off. I was feeling sexy as hell. I knew strange men were going to be checking me out and that one of those men actually thought I might fuck him. I was already wet.
We got in the car. The plan was to meet Dave at a local bar. As I sat I noticed how much my skirt slid up. If I moved even a little my panties would show. Jon moved his hand to my panties, pushed them aside and started playing with my pussy.
“Wow,” he said, “What’s getting you so wet.”
I just blushed. Truthfully, my mind was already back home with Jon and Dave getting fucked. Hard. I know I probably wouldn’t do it, but that’s what I was thinking about.
We pulled into the parking lot, parked, and started walking towards the door. My legs felt uneasy. I was hanging onto Jon. I felt like running but knew I didn’t want to.
We entered the bar. I looked anxiously around. The bar was not full. I saw Dave sitting in a booth. We walked over. Dave stood up to introduce himself. Next to me he seemed big. He had a big chest and shoulders. He was a head taller than me. My eyes were at his chest height. I had to look up to talk to him.
He shook Jon’s hand. He then looked at me and said, “you are 1000 times sexier in person.”
I liked the compliment and thanked him.
He said, “Can I see the back? I am a total ass man.”
Without even thinking I turned around. I was looking straight at Jon. David said over my shoulder. “Your girlfriend has a sexy ass. I hope I get to see more of it.”
I wondered what Jon was thinking.
Dave put his hands on my shoulders, kissed my forehead and said “you look amazing”.
To both of us he suggested we sit. I looked. The booth he had chosen was a rounded bench around a table. We all had to slide in. I slid in first, Dave on one side of me Jon on the other.
The conversation actually flowed easily. Dave was funny, smart, attentive, but not creepy. He made me laugh while throwing in a ton of compliments. With each compliment he got a bit more intimate. Some compliments were to me. Some were to Jon about me.
I actually felt hotter when he talked to Jon about me. I felt like someone who was going to be used and did not have a lot of power over it. The idea excited me.
As we chatted Dave would touch my arm, my hand, my thigh. Each time he touched me I felt a jolt of electricity. As we talked his hand focused more and more on my leg. I looked at Jon. Jon also saw where Dave’s hand was. Our eyes met.
We both knew I wasn’t moving Dave’s hand. We both looked at Dave. He knew we were giving him the go ahead. He commented on how soft my thighs were. I thanked him and subconsciously spread my legs a bit. His hand slid up and down my leg grazing my pussy with each stroke.
It was all driving me crazy. I decided to go to the rest room to breathe. When I got to the restroom I leaned against the counter and breathed. The reality is my panties were soaked. I could see my nipples hard against my blouse. I straightened my clothes and exited the restroom. Dave was standing there.
All I could say was, “Hi.” and shyly look at the ground.
Dave put his hand under my chin and said, “You are sexier than I expected. Fucking you would be a gift from God.”
I was shocked. All I could say was, “thank you”
Dave said, “I’ve been dying to see those panties you’ve been flashing all night.”
He stepped back from me. Looking me in the eye he said, “Show me.”
Being told what to do made my heart beat faster. We were standing in a hallway in front of the restrooms. Anyone could have walked by. Even knowing that I reached for the hem of my skirt. I pulled it up to my waist.
He said, “Nice.” and then motioned for me to turn around. “Very nice,” He said.
He took my arm, turned me to him and pulled me into his arms. I felt small in his arms. He looked down at me and kissed me. I kissed back. His hands dropped under the hem of my skirt and cupped my ass. As we kissed I wiggled my ass against his hands.
The kiss ended and we walked back to the table. Dave had his arm around me the whole way.
Dave looked at Jon and said, “I have a room across the parking lot. I’m taking your girlfriend. Would you like to come?”
It sounded odd but the truth is I was going. I liked the way he said “your girlfriend”. I hoped Jon would come too.
We all headed over to the room. As soon as we got in Dave kissed me. Jon was right beside me. Dave nodded his head that way. Still in Dave’s arms I gave Jon a passionate kiss.
Dave then pulled my top off. Slowly he bent over and started sucking on my nipples. This was the third guy who’d sucked my nipples. This time my boyfriend was watching. It was surreal and hot.
Dave looked at Jon, “Is she a good cock sucker?”
Jon said, “yes.”
Dave looked at me challenging me to prove it. I slipped to my knees, unzipped his pants and started sucking his cock.
Jon went and sat down. All the time I was sucking his cock Dave asked me questions or talked to Jon. It felt odd but exciting. I felt like a sex toy. In fact at some point Dave called me a slutty little fuck toy. I liked it.
He’d tell Jon how good I was, ask if Jon liked watching his little slut suck cock, and tell Jon how lucky he was to have this sexy little slut as his girlfriend.
To me he would ask if I liked his cock, did I like sucking it in front of Jon, how did I feel on my knees with a strange cock in my mouth.
I was getting off on answering his questions and listening to Jon answer. I felt free. I felt I could do anything. I could be as slutty/naughty as I wanted and no one would judge me. I was loving having this strange cock in my mouth.
Dave pulled me up to my feet. He stood behind me. I was facing Jon.
Dave said, “Take the skirt off.”
I unzipped it and let it fall to the floor.
Next he told me to walk over to Jon. I walked over in my heels and thong. When I got to Jon, Dave said to Jon “if you want me to fuck Your girlfriend take her panties off her.”
I was looking in Jon’s eyes. I was hoping he’d do it and hoping he wouldn’t. He reached out and pulled my thong slowly over my legs.
He then looked at Dave and said, “Fuck the shit out of her.”
It was time.
Dave came up behind me. He lifted my arms and put them on Jon’s shoulders. I was bent at the waist. My face inches from Jon’s. I felt Dave’s cock push against my pussy. I had had a hard time getting my lips around the tip. I could feel its size splitting my pussy. Jon could see me suck in my breath as Dave entered me.
As Dave buried himself all the way in me I let out an, “Oh my god.”
Here I was filled with the 3rd and biggest cock I’d ever felt, being bent over my boyfriend and looking in his eyes. God it was hot. I was all nerves, every part of me vibrating.
Dave said, “Ask Jon what he thinks of his slut now.”
I did as I was told. I got into it.
“What do you think? Is this the slut you wanted me to be? Being fucked from behind by a stranger while looking in your eyes? Is it turning you on? I hope so, because it’s really turning me on and I am pretty sure this will not be the last time you see me fucked.”
Jon grabbed my hair, pulled my face close and kissed me.
Dave kept pounding my pussy from behind. I felt the start of my first orgasm.
“Oh my god Jon, I’m cumming. Your slutty little girlfriend is cumming all over a strangers cock.”
The orgasm ripped through me. My knees buckled. David caught me and carried me to the bed.
Jon came over to the bed
To me Dave said, “Get your ass up.”
I didn’t have to be told twice. I got on my knees with my ass up in the air. Jon was sitting off to the side of us. Dave climbed on the bed behind me and started fucking me. Jon told me later he could see Dave’s cock, covered with my juices, sliding in and out of me.
Dave continued to tell me what a good fuck I was. I liked it. I wanted to be the best fuck he ever had. I grunted and moaned with each thrust. It was not long before I had my second orgasm. Dave felt it and stopped fucking me.
“Turn around,” Dave said.
I turned. My face was now facing his cock all covered with my juices.
“Suck it you slut.”
I did. I wanted to make him cum. I wanted it in my mouth, on my face, on my tits. As I sucked him I starting begging him to cum.
“Cum for me,” I begged. “Where do you want to cum? In my mouth? On my face? No ones ever fucked my ass. Do you want to fuck my ass and cum in it?”
At hearing that Jon’s mouth dropped open. He’d asked me to try anal, I’d always say no and here I was offering it to a stranger."
Dave liked that idea. “Give me that virgin ass,” he ordered.
I turned again. This time facing Jon. I put my ass in the air. Dave got behind me. He started probing my pussy with his fingers and spreading my juices on my tight assbud.
I looked at Jon. “Oh my god Jon. This guy is going to fuck my virgin ass before you.”
As I said it Dave started probing my ass with his thumb.
Jon pulled out his cock and started stroking it as he watched.
“Oh my God Jon, he’s got his thumb in my ass. Do you think he can feel how tight it is? I can feel him stretching me out. Getting ready for his cock.”
“What do you think,” I said to Jon. “Is this what you wanted? You can watch your girlfriend get her ass tucked for the first time?
Jon just smiled. He started jerking his cock in earnest. I told him to come closer. He did. I grabbed his cock and started sucking it.
I looked back at Dave. “Do it. Make my ass yours.”
My pussy was so wet the juices he spread on me had my ass well lubricated. He pushed the head in. I stopped moving. I felt Jon’s cock in my mouth but I did not move.
I felt my ass stretching. It hurt, but felt good at the same time. He stopped and waited for my ass to relax. Jon watched, stroking his cock, jacking off with my mouth around his cock, as slowly Dave buried his cock in my ass.
“Oh my god Jon. I’ve never felt this full. I’m going to cum. I’m going to cum with Dave’s cock in my ass.”
Saying that. Feeling Dave’s cock all the way up my ass. I came. I came hard.
I started screaming. “Fuck my ass. Fuck it hard. Fuck my virgin ass. Give me your cum. Fill my virgin ass with your cum.”
I started fucking Dave’s cock with my ass more than he was fucking me. As much as I tried I could not keep Jon’s cock in my mouth.
Jon watched. I could see him jerking off. I reached for his other hand and he took mine. I came again. As I did I screamed telling Jon that Dave’s cock in my ass was making me cum.
I saw Jon start to spasm.
“Do it Jon. Cum on me. Cum on me while I get my ass fucked.”
That was is for John. I could feel his hot cum on my face and back. I came again.
I felt Dave start to stiffen. I knew he was about to cum.
“Cum in me. Fill my ass.”
He did. I could feel it squirt in me. As he kept fucking me I felt some start to drip out my ass.
Dave pulled out of me. I got off the bed. Jon was sitting on the floor. I straddled him. My ass in his face.
“See it baby? Look. There’s another man’s cum dripping out my ass.”
Jon kissed both my ass cheeks. I went back to the bed, took Dave’s cock in my mouth and started licking and sucking it clean. I could feel him getting hard again.
Between Jon and Dave the next 6 hours were a blur. A very satisfying blur.
On the way home i had a face covered with cum and smelled like sex.
“Well Jon, was it like you imagined.”
Jon looked at me and said, “Better.”
I laughed. I laid back in my seat, pulled my dress up, and started playing with my cum soaked pussy.
As I did, I said to Jon, “I wonder if your friends want to fuck me.”
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