1 comments/ 17232 views/ 5 favorites Craigslist Sex By: switchhitter Glenn has received a lot of emails asking for me to tell my side of our adventures. This is just one of many I plan to share. Hope you enjoy ... Carol. * During my separation in 2009, I was looking for an apartment in the local paper, by word of mouth and Craigslist. I found a place within a week. While looking on Craigslist I saw the personals and a link called 'Casual Encounters'. Out of curiosity I clicked on it. There were links men for men, men for couples, women for women and so on. I sure you know what I'm talking about. Scrolling down there was one that caught my eye "Looking to please m4w-35" and it had a picture. I opened the post and my jaw dropped. It was a photo of a man 12 years younger than myself at the time. His cock was gorgeous! The ad said something about how he was married and his sex life was nearly nonexistent. Needed to be discreet, DD free and said his cock was over 8 inches and so on. He could not host. I'm thinking to myself 'should I answer this guy'? After a couple of days of starring at his beautiful cock, I decided to answer his ad. I kept checking my email every 15 minutes of so for a couple of hours. Nothing. Later that evening I checked again. There he was in all his glory! He had sent a few more photos of his hard lovely cock and his cell phone number asking me to text him. I did it! I sent him a text. "Hi, I like your post. Are you still interested?" Within an hour he texted me back. He said he was still interested and asked me for my 'stats', which I told him. After a few texts back and forth we decided to meet the upcoming Saturday afternoon. It was a long two or three days before Saturday. We met at a small restaurant at the local mall. He was standing outside the door. We introduced ourselves and went inside. It was a bit crowded but managed to get a booth in a corner. We ordered a couple of beers to start. We made some small talk while checking out the menu. After ordering, he told me how pretty I looked. I told him that I also found him very attractive. Kyle, his name, stood around 6 foot tall, great build, brown eyes and hair. He said he weighed around 170. Our lunch came and started to eat and talked some more. I shifted in the seat and mistakenly hit his foot with mine. I apologized and he said that's OK, next time you bump me, just make it a little higher! I laughed and told him he was fresh. He smiled. Then it came over me. I thought to myself that soon I'm going to be having sex with guy. So feeling a little horny now, I took off one of my shoes and started rubbing the inside of his calf. He looked at me with a surprised look on his face. I told him that I'm not sorry this time. I took my foot away and he something like 'you can go a little higher if you want'. I did. I went up his thigh and found his hard cock. I continued to rub his cock with my foot as he was trying to eat. After a few minutes of this he said if I continued doing this he was going to cum. I suggested that we go to my new place. He agreed. He paid the check. We went arm and arm to our cars. He walked me to my car. His was just over in the next row. I got into my car. When I got settled, I looked over at him and noticed he still had a hard-on. I rubbed it and told him I can't wait to get my lips around it. He said he didn't think he could wait to get to my place without blowing his load. He asked if I would blow him right here. I told him that I love public sex, but not in bright daylight. Then I got an idea and told him to get in the car and pull his pants down. I've never seen a guy move so quick! I drove to the end of the parking lot where it was empty and no one around. I parked and put my head in his lap. His cock was big, and thick too. I put the head in my mouth and I could already taste his pre-cum. His cock was too long to take down my throat, so, with one hand I stroked while I sucked and rubbed his balls with the other. I don't think two minutes went by when he said he was going to cum. Having about half of him in my mouth and without bobbing my head, I used my tongue to get him off. He groaned as he started shooting his cum into my throat. I had to swallow quickly because he just kept unloading. As he started to settle down I slowly stroked him to get the rest out of his dick. I used my tongue to get the cum that was down the base of his shaft and my hand. I looked up at him and told him that he had the best tasting cum I've ever had. I took him to his car and told him to follow me to my place. My place still had boxes and junk laying around from my move. I told him to make himself comfortable on the couch. I had to pee so when I got back he did make himself comfortable by taking off all his clothes. I looked down at him and said I see you're ready to go. His dick was already stiff again. I took off my clothes and sat right on his cock. It felt soooo good having a big one fucking me as he sucked my large breasts. This guy knows how to fuck, I thought to myself. Within minutes he had me Cuming. I got up off of him and told him to fuck my doggie style. Oh, he feels so good sliding in and out of me, stretching my pussy walls. I came again and again. I told him not to cum inside me when he was ready. He asked where he should cum and I told in I wanted his cum on my face. Soon he was ready. He pulled out. I turned around so he could straddle my shoulders. Blast after blast hit my on the nose, forehead, mouth, cheeks and lips. I love a man's cum on my face. It makes me feel dirty and I know men love to see their sperm on a woman's face. Anyway, he took his cock and gathered the cum so he can watch me as I open my mouth for his spent cum. After fucking and sucking throughout the rest of the day, we were both exhausted. He left early that evening. I gave him my phone number and told him to call me anytime he needed to 'let loose'. He called me two days later and got back together again. We got together several more times before he said that his wife was getting suspicious. We keep in touch from time to time having phone sex, but it's not like the real thing. Hopefully one day soon, Glenn (my boyfriend) will have the pleasure of watching Kyle, a man with a real dick bang me shit out of me. Craigslist Sex I'm simply a 19 year old college student, but all of my sexual life I've wondered what it was like to be with a woman. I'm 100% straight. I've had boyfriends, I've had sex with them too. But I've always wondered what it would be like to make love to a woman. One night I was reading a story on this site, and the main character put up an ad on craigslist. I went on craigslist and decided not to put up my own ad, but to answer an already existing one. I found an interesting one, and for her sake I'll change her name to Alice. She's 43, but looks as if she's no more than 24. She also had a husband and two kids, but said she wanted a plaything on the side. I emailed her about her ad, and got an answer a couple days later. I found your ad on craigslist and was emailing you to let you know I was interested. What a nice surprise. Is what I got back. Yes. I've never been with a woman before, and I would really love to try it. The subject line of the emails, still present from her ad on craigslist, read "Let's sext, exchange pictures, possibly meet up". She emailed me back saying that we should give it a go and we can either exchange numbers or go on kik or yahoo messenger. First we tried yahoo messenger. She told me that the first time she was with a woman was a year ago, on a drunken night and that in April she's made out with a woman. I asked her if the only time she had been with a woman was when she was drunk and she answered no because they woke up the next morning and did it again. The other woman had tied her up, and continued to fuck her with her mouth. That sent a shock to my pussy. She also told me that she would love for my first time to be with her. She said we could take it slow, starting off with a couple glasses of wine, caressing each other, and stealing a few kisses. I have large breast, a whopping 38DD, and she told me how she can't wait to pinch and suck my nipples. We talked dirty for a while longer, before she told me to download kik, a messenger app where you can send pictures and videos. She sent me a picture of her cunt, which was natural. Next was her breasts, her nipples sticking out so far. I wanted nothing more than to have her run them along my sopping wet pussy. I sent her a picture of my sex, and she told me she couldn't wait to get her mouth on it. We went back and forth, and next I got was a video. She had a magic bullet, that came free with the purchase of her 8 inch purple strap on that had a place for the bullet so it aligned with my clit. The video was Alice rubbing the bullet on her clit until she orgasmed, her sexual moans filling my ears. She went to sleep eventually, and so did I. My dream, my dream is really what I wanted to talk about. Alice lives in a place where it's easy to get to on public transportation, which was good for me because I didn't have a car. We had been planning this day for weeks. I've been away at school, masturbating to the videos and pictures she would send me. She opened the door and smiled at me gently, inviting me inside. Her husband was at work and her kids were at school, so we had the whole house to ourselves. She brought me to the couch and already had to glasses of wine poured. We sipped on it, just talking. "How is school going, honey?" "Good. My first semester just ended, and I think I did good on my finals. I was so stressed about it." She stroked my upper arm. "I'm sorry, honey. Well you're with me now, no more stress." She placed a soft kiss on my lips, my first kiss with a woman. She pulled back and took both our glasses of wine and placed them on her coffee table. She moved closer to me, draping her leg over mind and capturing my lips again. This time our lips parted, her tongue darting into my mouth. Her left hand was on my neck, keeping me to her while her right groped my large breasts. My nipples pebbled underneath my shirt and bra, and I moaned into her mouth. "Let's get you out of this shirt, huh?" She slipped both her hands under my shirt, lifting it over my head. She continued kissing me, reaching behind me and unclasping my bra. "Wow," She whispered as she admired my titties. Soon she was attached to my right one, sucking like no tomorrow. My head fell back as I moaned, her tongue teasing my hard nipple. She soon switched to the other one before taking off her own shirt and bra, revealing the nipples I had only seen in pictures. "It's ok to touch them, honey." She said to me. I looked in her eyes before leaning down, shyly licking her right nipple. It instantly hardened, and I sucked it into my mouth. I softly pinched the other nipple between my index finger and thumb. She pushed my head back, and silently lead me to her bedroom. She laid me back on her bed, laying on top of me. She kissed me again, once again playing with my nipples. She kissed down my body, leaving a fire hot trail. She slowly peeled back my leggings and panties, slowly revealing my soaking wet pussy. She threw them to the side, long forgotten. She slid her hands up my legs, spreading my thighs. She kissed each on and around my pussy, not dare touching where I wanted her most. "Alice, please." I begged, pinching my own nipples. She smiled up at me before giving me one, slow lick up the length of my sex. My eyes rolled to the back of my head as a loud moan slipped from my lips. She sucked my other lips into her mouth. Her tongue soon found my hole and entered my body. I screamed her name as I felt her tongue fuck my tight pussy. She took it out and started working on my clit, and that's when I lost it. She never let go of my clit as an orgasm coursed through me, her name the only word in my vocabulary. She lapped up the rest of my juices, and kissed back up my body. She kissed me again and I could taste myself on her. "I'll be right back." She smiled before jumping up and leaving the room. I marveled at how wonderful I felt. I rubbed my pussy, relishing in my orgasm high. She came back, and I gasped. She was wearing the purple strap on that she told me about, equipped with the magic bullet on top. "I'm going to fuck you so hard and make you squirt all over this cock, baby." She came back to the bed, and positioned the dildo at my still sensitive pussy. She switched on the magic bullet before slowly entering it in my pussy. As the dildo was sheathed all the way inside me, the bullet vibrated against my clit, making me squirm. It felt so good. "Fuck me, Alice! Fuck me hard!" And she did. Better than any man I've ever been with. I orgasmed four times that day. She let me eat her out, and I think I did a good job from the way she was grinding her wet cunt against my face. We were cuddling when I woke up from the best wet dream I had ever had. When I woke up, all my clothes were off and my index and middle fingers were inside my dripping wet pussy and my sheets were soaked. I quickly changed them before my roommate saw, and I can't wait until I go home for Christmas break. Craigslist Sub I got married way too young to a really sweet man. I was happy sure, but bored out of my mind. I had kinky dirty thoughts and couldn't share with my husband. He was so wholesome, he'd be mortified. For several months I read personals online and fantasized about the man who could make my fantasies come true. Only after my 12 year anniversary at 32 years old, did I get the nerve to put up an ad and find a master. I considered my options carefully. I am attractive, average body, successful career woman. I'd need to find someone who seemed smarter than me, more powerful, able to take control. I found it hard to take a lot of the men seriously, especially if they sent replies full of slang or incorrect grammar. I also was sure I needed an older man. I put an ad on Craigslist. It read, "Looking for one special dominant man who will help me explore all of my fantasies. Must be 45+, fit, married and able to host. Must want no long term friendship or romance. This is strictly for very kinky sex. It is about my fantasy, which is to be your slut." Immediately I started getting responses. Guys who were 18. Guys who cannot host or meet during the days. A few single men. It was so discouraging. I finally found 4 ads that seemed to match what I was looking for. I replied to Dirtydom first. Asked for a photo and sent him a naked body shot of myself. He wrote back what he was into, and ignored my request for a photo. He sounded very into pain, which is not my thing. I was looking for something else. Next I replied to CallMeSir, who was polite and sent me photos right away of his face and his body. I was a little annoyed because I asked about body and didn't know yet if I wanted to ever see the face. I had not formulated my plan. But I continued to talk to Sir. He was 54, 5'8", fit, salt and pepper hair and handsome. He was open to anything I wanted and took over the conversations right away. It was natural for him to take control and me to be submissive. Even better was that he had a house in Ct with his wife and an apartment in the city. I was sold. I told Sir through email that I wanted to push myself. My fantasies focus around humiliation, being a total slut. Doing things no one who knew me could ever imagine. He assured me that he could make me feel like nothing but a dirty, worthless cunt. If he accepted me that is. I was dripping wet and totally hooked. Sir told me he would meet me and interview me IF I agreed to have no limits. I had to trust him to make every choice for me and let him control everything. If ever I wanted out, I could just say Out, but that he would never see me again if I choose to take the out. That seemed so easy to me. I do what I like and have an out anytime. I agreed quickly. I met Sir at a fancy oyster bar in the bottom of his building. He was at a table, striking. I walked up to him smiling, feeling nervous but also sexy and excited. I had worn a black pencil skirt and a pink sweater. As I sat down, Sir did not smile. His first words to me were, "Did you not think I deserve you showing up here looking sexy?" I was shocked and embarrassed, totally deflated. I mustered an apology. "Go to the bathroom so I can see your ass" he ordered me. I got up and walked self-consciously to the bathroom. Once there, I stared in the mirror and thought to myself that I needed to leave. Who was this asshole who thinks he can talk to me like some desperate slut? I felt angry. Humiliated. And so turned on. I walked back to the table and calmly asked Sir if he was happy with what he sees. He replied that I look OK, usable and asked if I was ready for the audition. While my mind told me no, my mouth said, "yes sir." Sir finished his scotch, stood up and told me to follow him. I walked behind him to the elevator. We got inside and road to the 32 floor. I realized I didn't even know his real name. What the hell was I doing!? He walked down the hall to apartment 32D and lead me in. "On your knees slut with your sweater and bra off." He said. I stood there in a daze, not responding. "I don't repeat myself you stupid whore, do it now." I snapped out of it, pulled my sweater and bra off freeing my 36 Cs and dropped to my knees. He bent down and slapped my tits hard enough to leave read hand prints, then squeezed my nipple tight. It stung and made me gasp. I saw his first smile ever as I gasped. He stood and got close to me, crotch in my face and told me to take his pants off. I reached up and unbuttoned his pants, slid the zipper down and pulled them down. He slipped his shoes off and tossed his pants aside. He had boxer briefs on showing an outline of a long, hard cock. "I see you drooling. Tell me what you want cunt." "I want your cock sir," I said faintly. My heart was beating now and I was scared. I thought about saying out and going home to my sweet husband, but I didn't do that. Instead, I sat there like a depraved slut dying to please this cock. "More specific cunt, what do you fucking want?" He said loudly. "I want to suck your cock sir." I said. He looked at me, no reaction. "I want to suck your cock sir please." "Dirtier slut," "I want to suck your big cock sir. I want you to fuck my throat and use me like a whore. I want to choke on your cock and drink your cum." "Alright you stupid slut, get going." With that I reached up and pulled his boxers down. His cock was long, about 8 inches and thicker than my husbands. I felt like such a slut as I grabbed it. Feeling my pussy juice running down my leg, I started licking his cock like a lollipop, then put my lips around it and sucked it down. I went as deep as I could, taking 5 inches or so, stroking him while I did it, flicking his juicy cock head with my tongue on the way out. He was hard as a rock. Suddenly without warning, he grabbed the back of my head and shoved his cock all the way into my throat. I choked and couldn't breathe. He held it there a few seconds, then pulled it out. As I gasped for air, he slapped my face and spit on me. He then shoved his cock into my throat again and started the process over. He did this awhile, then pulled out and turned around. He told me if I couldn't make him cum, then I failed the audition. It was the most humiliating moment of my life and all I could think of was trying harder to please him. All I wanted was his hard cock fucking me and I knew I'd do anything for that. He sat on the couch and raised his legs. "Lick my asshole bitch." I had never done anything so disgusting or even thought about it, but I didn't miss a beat. I scooted in and smashed my face into his ass, his balls resting on my forehead. I licked his puckered asshole like I wanted him to lick my clit. He reached down and squeezed my nipples hard, pulling and tugging on my tits to the point of pain. "Good slut, you are a nasty one," he said with a chuckle. "What a low class piece of shit you are, licking the ass of a total stranger. You don't even know my name. I didn't even buy you a drink!" His laughing at me made me drip even more. I had never been so wet in my life. "Show me how you worship balls whore." I moved up and took his balls in my mouth, one at a time. Being 20 years older than my husband they seemed wrinkled and saggy. I licked them and sucked them lightly while he stroked his cock slowly. The way he was leaned back, I could see his face. He held up a cell phone and took a photo of me with his balls in my mouth. He laughed some more. "You want my cum whore?" He asked with a smile. "Yes sir," I said like a desperate slut. He slid his cock deep into my throat again and started cumming. It was thick and hot and choked me. He pulled out and shot a big string onto my forehead, then another right into my mouth, dripping down my chin to my tits. He took another couple of photos of me then said, "Get out of here and be back at 10am tomorrow." As I stood up, he reached up my skirt and slipped his hand under my wet panties. Laughing he said, "Wow, you fucking whore loved that! You should be ashamed of yourself you little cunt." I asked to use the bathroom to clean up. He paused for a moment, then smiled ear to ear. "You can either leave as you are or let me clean you up." I said "Please clean me up," knowing I couldn't go home on the subway covered in cum. He told me to take my skirt and panties off and follow him to the bathroom. I did as he said. He put me in the bathtub and told me to stay on my knees. I sat there on the cold tub waiting for him to turn the shower on. I was still so horny and dying to cum, but thought it felt nice to be washed and cared for. Just as I was feeling safe, Sir came to the edge of the tub, aimed his softening cock at me, and started pissing all over my face. Not expecting it, I moved away. He quickly slapped me and told me that if I didn't hold still, he'd make me keep my mouth open too. I stayed super still with my jaw clenched and my eyes closed feeling his piss hit me from my hair down to my tits. He was laughing and calling me names. I couldn't focus anymore. I felt tears run out of my eyes. When he was done, he told me to shower and get the hell out. When I came out of the shower he was dressed again. I rushed to the door. He said "10am tomorrow?" I stopped at the door and nodded yes, then rushed out of there. I stopped at the closest starbucks and went into the bathroom. I had to cum. I rubbed my clit and came super hard in minutes. Then I went home to start dinner.