Giving it up on Craigslist

My wife was finishing her graduation, and I hadn't had sex in months. And since I couldn't get the real thing, porn started to fill up the gap. I started frequenting porn sites more often (even with my wife sleeping right next to me). As the months went by, the normal porn progressed towards kinks (from my perception) and one of those was deep throating as well as swallowing. About me - I am weirdly a mix of masculine and feminine traits - strong headed, aggressive, dominating and never back away from a fist fight but I have a very feminine look, pretty face (as my wife and friends, both male and female put it), hairless chest with average build. So that might have played a part in making me more curious about how it really feels like to get a cock down your throat, to let a guy cum in your mouth and to have a cock in the ass to experience the so called prostrate orgasm.

The more I watched the videos, the stronger my craving for a cock became. I have been lucky to have a wife who lets me ejaculate in her mouth when she sucks me (she doesn't swallow though) and know how heavenly that feels. I have also had her ass (just once though but she had begged me for it which made it really memorable) and it was fun. Of course I am straight - have been attracted to boobs and asses (females) since the day I started getting hard ons, not for once attracted to men, but for just this new curiosity.

So I looked for online for safe things to try out this new curiosity, got some good advices as well as tips and got myself a small (thick as a thumb and about 4") and medium sized (about an inch thick and 6") dildo. When my wife left her classes, I tried the deep throat first, but no matter how much I tried to relax my throat, just couldnt get past the gag. I then tried getting down on all fours, lubed up my hole, and started inserting the smaller dildo in my ass. It was hard. at fast, but as I relaxed my muscles, the dildo slipped in easily. Then i tried the bigger one, and it took some more effort, but that went through as well. But no orgasms. No fun either.

I tried a few times after that but failed in both. Somewhere around that I decided that I do need to experience the real thing and not inanimate objects. Craigslist personal was still active then, and I went online to search. That was my first time on Craigslist personal and i was shocked to see what happened there. It seemed like I needed some pics and when I tried to browse for ideas, I found those pretty hot. In one pic a sissy guy was on all fours facing the camera, a red ball gag in his mouth, with his naked ass stuck out from behind him and felt like he was offering his body for another man's pleasure. In another one, he was licking an upward curved cock sexily. I had a hardon just looking at that. So, I decided to go with the first pic, and took one of my own very similar to the pic I saw. I then created a craigslist profile offering to suck a guy, promising to finish him in my mouth and if things went well, let him use my ass. And waited.

When the first response came in my inbox in just under a few minutes, i was thrilled. The feeling that somebody "wanted" me brought up some sort of feminine instinct in me. I knew he had so many 'girls' to choose from and felt proud to be chosen, and just longed to please him and give him the best sex. And then within the next 20 minutes I had tens of more interests. For the first time, I could feel what women must feel all the time. The luxury and options to choose who gets to fuck them. Truly an empowering feeling.

I finalized on four guys - a 57 year old married Greek man who wanted to meet at his office warehouse in the outskirts, a 45 year old european guy who only wanted a blowjob at his home, a 28 yo single black guy who wanted me to meet at a motel, a 28 year old Pakistani guy who wanted to have me at a gay camping site and another 18 year old Indian guy who was still living with his parents. I quickly rejected the Indian guy since according to him, I would have to come to his house, where his parents would likely open the door and I would have to say that I was a private tutor, then get fucked by him while his parents go on with their day downstairs - could it get any weirder? The black guy had a nicest cock (not like porn movie but still big, thick and very chocolaty) but it was a little scary when he casually mentioned that his friend also thought my ass was made to be spanked and fucked. It felt hot to be lusted by not one but two black men, but I was afraid that what became two cocks so fast could become a gangbang (blame the porn movies for that) and very easily get out of control. The Pakistani guy looked nice - masculine face with a trimmed beard, nice build, tanned skin and an average sized but meaty cock. The problem was with the travel. The campsite was 2 hours away and though the onward journey would still be ok, the return journey would be very awkward. I mean how do you sit next to a guy who spends a full night cumming in your mouth and ass? As attractive he was, I dropped that option. And settled on the Greek guy.

We exchange emails for a few days while I chickened out a couple of times. In the end I was afraid of getting caught, or ending up in some sort of trouble if the guy secretly takes photos of me and posts on internet. But finally one evening when I was really horny, I agreed to him. He really wanted a pussy to fuck but had to settle for guys like me since he was getting old, so he kept referring to me as his boi pussy. As per his wish, I wore a lace panty, light lipstick with gloss, just a bit of blush (all internet learned) and drove to the ware house. I still didn't want him to fuck me in the ass because it just felt weird, dirty and not appealing.

He received me at the door. It was a dim lit place and he pointed towards the bathroom and asked me to undress, then come to his room where he was sitting naked on a chair. I really felt shy and looked down at the floor as I entered his room naked and had to walk up a few steps to him, unable to look him in the eye while he sat there naked like a king about to be pleasured by his concubine. It felt that shameful. He asked me to kneel in front of him and though I was still looking down, I could feel him waiting for me to initiate. So, I slowly looked up towards his groin and I felt my heart jump out of my chest. His soft, limp cock looked so cute, that all I could think of was to kiss it, play with it and suck it to a nice, perfect finish. I slowly bent forward, and kissed the tip. Then licked half the length of it. With my cold and sweaty palm on his thighs, I wrapped my tongue around his meat and lapped up the head into my warm waiting mouth. I could sense his thigh muscles tensing up, and felt my first happy feeling of the evening. I nibbled and played with his soft meat while it slowly came to life and soon was curved hard into my mouth.

I took his hard cock in my hand and licked up from his balls all the way to the tip, while spending just long enough at the base of the head to make him squirm. I took the cock back into my mouth and started sucking him as erotic as I could manage. I tried to deep throat him a couple of times but both times my gag was too strong. Mainly because of the upward curve that was continuously hitting the back of my throat, instead of sliding in with the curve. I enthusiastically sucked him for a good ten minutes until my jaws felt sore. I tried to deep throat again but failed.

He obviously saw my attempts to please him and he offered to help with it, and asked me to lie down on the carpet, face up. He then kneeled over my head facing my feet, and positioned himself so that his cock was right above my mouth. Then proceeded downwards till his tip pushed against my lips. "open up" to which I obliged and felt him push his cock past my lips towards my throat. The first gag reflex was strong but he just held his cock steady and said "relax". As I overcame that gag, and relaxed my throat he pushed forward more triggering a second one. When I was able to relax again, I felt his cock slide fully into my throat and his grey pubes and balls choked my breath. But I felt a huge sense of achievement having finally been able to get a real cock in my throat.

He started to slowly throat fuck me and though it wasn't particularly pleasing for me, I let him since I really wanted to please him and wanted to be the one to give him the best sex of his life. Before I realized, he had sneaked his middle finger inside my ass and was slowly fingering it. I felt shocked and disgusted at first since I had no plans to have anal with the man, but weirdly enough still longed to please him, so didn't object and instead pulled in my legs giving him a better access and in a way giving him the go ahead. In fact, I sort of felt honored that he was lusting for my ass. After what seemed like a long time but probably just a few minutes, he rose up and said "wait here", then walked over to his desk and pulled out a condom.

I was still lying on the floor when he handed me the unopened condom, got back on his knees over my chest and resumed fucking my face. After a few strokes, he signaled me to roll up the condom on his cock, and scooted back to position between my legs. He lifted my legs up in the air, positioned his hard cock at the entrance and started pushing. Unlike the dildos I had, his cock was much thicker and I could feel the pain as the head pushed against my hole. I could hear my own grunts as the head finally plopped in, and then slowly slided inside my ass. And then the fucking started.

He started slow, but soon my legs were over his shoulder and he was giving me a rough fuck, while roughly kneading my man boobs and shouting expletives - "you fucking whore" "fuck you are tight" "you piece of slut" ... it was erotic for me, and at the same time it hurt. I let out loud grunts, a weird mix of pain and unknown sensations, which he took for pleasure and fucked me even harder.He bent his head and I felt his lips and tongue tip nibbling on my nipples, and I couldn't admit it, but it felt good. He then tried to french kiss me and I resisted to which he said "give me your tongue". I couldn't dare to ruin his perfect sex moment, and like an obedient slut, let him suck on my tongue as he pleased. It felt nasty and unclean, and when he darted his own rough tongue into my mouth exploring, it exponentially increased that dirtiness. But I still let him do as he pleased.

After not so long, probably five minutes or so, I felt his face quicken and his muscles tense. For the first time I could feel why women placed such an emphasis and sense of pride for bringing their men to orgasm. There was just an explainable satisfaction of making the man cum for you. It signaled that I and only I was to credit for achieving his orgasm, to get him to that heavenly feeling he was going to have. All because of me and that felt amazingly satisfying. I reached out and grabbed his ass digging my nails into his soft tight flesh. And that was the final straw that did the job for him.

We had a deal that he wouldn't cum inside me without a condom, and I was genuinely shocked as I felt warm cum fill up deep in my god knows where. My eyes and jaws snapped tight out of betrayal, whereas my butt muscles clenched up tight around his cock, milking him as he slowly spasmed in ecstasy. My legs were beginning to hurt and I repositioned those around his waist, drawing him closer as he lied on me, spent with his cock still buried in my ass. I slowly stroked his hair lovingly. Somehow all of the things - his dick nestled in my ass, the fact that he just cummed inside me and had filled me up with his cum, my feeling of pride in making him cum and giving him a shattering orgasm - made me feel connected with him. Made me feel as if I needed to take care of him.

As I stared into the ceiling absent mindedly, the events of the night replayed in my mind. The excitement of seeing a real cock eagerly waiting for me, that moment when I first sucked him, the pride I felt when I had the cock sliding down my throat, the lust filled face fucking, the first time of having a finger probing in my ass, rolling the condom down his cock, the moment of accepting his cock in my ass, his kneading of my boobs ... that's when I felt the first pang of regret.

I suddenly knew that it couldn't be the perfect sex for him. He wanted boobs. He probably wanted a bigger ass too. He seemed satisfied but he was probably not. My body just wasn't perfect enough. I started to wonder how his eyes would have light up if I had real breasts like a real girl. How he would have enjoyed my nipples more if they would have been larger, more womanly.

I snapped back to the present, when I felt him stir. He gently kissed my chest, and slowly raised himself on his elbows, propping up besides me as I released my legs from his waist. With one leg still sprawled on my thigh, he looked into me. His hand moved up and a finger started lightly flicking my nipple. His face bore the after glow of orgasm, eyes half closed as in dreams. My chest beat with excitement as his lips parted and I heard him say "that was mind blowing. you were amazing".

His words were music to my ears. And my heart flapped happily listening to his stamp of approval. It meant so much to me that I smiled. He bent forward again and kissed my lips gently once again. I felt my eyes close and my lips part for the next deeper kiss, which never came. Instead I heard "you should leave from the back door" as I felt his body lift itself and already walking out by the time I opened my eyes. Lying there naked, with cum leaking from my ass, I felt cheap and used for the first time that night. And I instantly knew that there was nothing special about me for him. All I was to him, was a nice fuck that was now done with. my eyes welled up as I hurriedly got up, grabbed a tissue and wedged it between my legs to stop the leaking cum. I grabbed my panties on my way out to the bathroom, and put it on. All I wanted to do was to grab my clothes and run to my car. Just not face him anymore.

He was holding the door open for me when I got there, clothed but the shirt still unbuttoned. I kept my gaze low, and felt his eye leering on my half exposed ass. As I squeezed by him through the door, his palm came down fast smacking my ass unexpectedly making me jump with a squeal. 'bastard' I murmured to myself with a smile. I heard a faint victory chuckle just as the door lock turned.