2 comments/ 12590 views/ 2 favorites Judi The Cockteaser! By: Bi_Siamese I married Judi when I was 27 years old. I was a tall, dark, and handsome stud looking for pussy rather than a relationship. When I met Judi, a blond 110lb. 5ft. 4in. bombshell with beautiful 36C breasts five years my senior and a lot more mature than myself I was easily swayed to submit. Judi was raised as a street smart woman hotel hooking in New York City on weekends for extra money. After high school and she learned the advantages of having several close lesbian girlfriends to escape the outside world. Having made enough money she left to the East Coast moving to southern California looking for a naïve younger male to take care of her. I definitely was not ready to be in a relationship with a woman liked Judi. After teaching me the art of cunnlinigus Judi got bored of my mouth and we parted ways. We kept in touch over the phone and sometimes when we got lonely we would meet for coffee and usually end up in bed. I was always drawn and to Judi's dominant nature and she enjoyed taking advantage of my submissive nature. Whenever we met there was always a cost because Judi knew every trick in the book to collect from me making me feel good at the same time. Being a skilled cock teaser Judi loved promising sexual favors to get me to do her bidding. When she was in the mood she loved drinking coffee, smoking cigarettes, and talking dirty on the phone. Judi had a way of sharing her sexual experiences without sharing any names only speaking in the past of things she had done. Knowing that I was gullible she could easily embellish her stories to make them so sexually exciting she could talk me into doing anything for her. We were actually having phone sex before phone sex was invented. On a hot summer days Judi would describe how she was stripping off all of her clothing one garment at a time until she was completely naked. She described how she was sliding into her silk sheets slowly rolling her middle finger around her clitoris as she talked. I didn't believe her until one day she invited me over to watch her strip for me. As my punishment for not believing her Judi told me that I could watch her get naked but there would be no touching or lovemaking and I would have to leave as soon as she demanded. Reluctantly I agreed knowing that Judi was a real tease. Greeting me at the front door with a warm hug and kiss Judi escorted me directly into the bedroom. Looking me directly in my eyes with her piercing blue eyes she told me she was disappointed in me and for doubting yet she was going to make my dick hard anyway and then kicked me out. Forcing me to sit in a chair next to the bed she told me to unzip my pants and pull out my cock but don't touch it. Unzipping my pants I pulled up my limp cock. Closing the bedroom blinds Judi lit up a cigarette puffing nervously blowing the smoke in my face. After another drag she set the cigarette in a nearby ashtray cursing me saying that she is going to really enjoyed making me suffer. Standing directly in front of me warning me not to touch her Judi reminded me that as soon as she was naked and rolling in the sheets she was going to kick me out. Smiling, Judi slowly began unbuttoning her black blouse revealing a beautiful black lace brassiere which pushed her shapely breasts together beneath. I could see her excited nipples through the material faintly covered by roses. Tossing the blouse over my left shoulder Judi pushed her scratchy bra into my face rubbing my cheeks and teasing my lips with her nipples telling me that this is what I'm missing out on by not believing. I could feel my cock starting to rise even though I knew I would be sent out the door with a bad case of blue balls. Next Judi grabbed her skirt unzipping the back then wiggling her sexy hips allowing it to slip down to her feet revealing a matching pair of black lace panties delicately and showing off her swollen pussy. Pushing her right hand down the front of her panties I could see her worming her two middle fingers deeply into her pussy. I watched as she fingered herself getting both of us quite turned on. Pulling her fingers out of her pussy she surprise me by rubbing her juices under my nose to smell and on my lips to taste telling me in a sexy voice that if I didn't doubt her on the phone I would be and licking her pussy right now. Placing her fingers back in her pussy retrieving more of her juices she grabbed my shaft and squeezed until my cockhead got purple rubbing her juices all over it telling me this is as close as my cock will get to her pussy today punishment for not trusting her. Hooking her thumbnails into the sides of her panties Judi turned around so that I could see her sexy ass as she slowly gyrated her hips pulling her panties down slowly to her knees letting them slip to the floor. Grabbing up the panties I watched her wiggling her butt as she pushed the crotch into her pussy and collecting all the juices she could. Turning around Judi revealed her shaven snatch which was already dilated and ready to fuck giving me that such a hot visual I was raging hard. Before and I could object Judi grabbed my chin pulling my mouth open stuffing it with her wet pussy juiced panties. Instinctively I started sucking the crotch of Judi's panties getting drunk on her taste. My brain went into overdrive as I was reminded of all the time I spent under the sheets licking her pussy. I could hardly sit down I was so turned on. I wanted to pick her up throw her on the bed and push my tongue into her pussy. Slapping my face back and forth Judi told me she knew what I was thinking but today it would be against the law because she was calling the shots. Reaching behind her she unfastened her brassiere releasing her huge breasts in my face tossing her brassiere over my left shoulder. As I continued sucking her juices from her panties Judi began rubbing her breasts all over my face teasing me with her hard nipples. Ordering me to stand up Judi unbuckled my pants pulling them down to my ankles. Next she yanked my shorts down to my ankles as my huge erection stood at attention getting no attention. Pushing me back on the seat Judi pulled off my pants and shorts. I couldn't talk because I was still sucking her panties but now I thought she was definitely going to take me to bed. Instead Judi ordered me to take the panties from her mouth and as I watched her seductively dancing her naked body she wanted me to place the panties around my cock and masturbate into the crotch until I came. I was so turned on there was no time for embarrassment. I quickly encased my cock with her scratchy panties and started masturbating watching Judi slowly caressing her naked body. Trying to be as nasty as possible Judi was pinching her nipples hard with one hand and fingering her pussy with the other taking time to give me and several licks of her fingers constantly reminding me what my tongue was missing. Opening her legs wide she grabbed her labia lips pulling them apart showing me the insides of her pussy telling me and this is where I could be coming in instead of her panties. As soon as she said that I started shooting into the crotch filling it with steaming sperm. I must've squirted a good ten times as I greedily squeezed my cock until I wasted all of my come in the panties. In her rough dominant voice Judi demanded that I slip the panties on myself. When I hesitated she slapped my face and told me to do it. Slowly I slipped them on with the crotch full of my own come which was now slowly sliming all over my cock. I barely fit into the panties which encased my cock and balls so tight I could hardly breathe. Watching my semen oozing out of the panties Judi only giggled telling me to pull my pants up because it was time to leave. I knew she was serious but I begrudged getting dressed. Pulling back her covers Judi's slipped into her pink silk sheets; the same ones she described or the phone and that I didn't believe she had. Opening her nightstand roared she pulled out a vibrator pushing it into her pussy telling me that if I hadn't been such an idiot I would be in bed with her right now. Pointing to the door and she told me to get out and when I get home to give her a call as soon as I got in the door. I left a defeated man with my head down totally humiliated by the experience. By the time I got home my jeans were soaked and I had to hold my hand in front of my pants to get to my apartment door so that no one would see. This time and I decided to obey and do what she told me to do so I gave her an immediate call. The phone "rang and rang and rang" and finally on that fifth ring Judi slowly and picked up the phone knowing it was me. Sounding euphoric I knew she had just had an orgasm from the vibrator. I immediately started to apologize for questioning her on the phone. I told her I would do anything to make it up for her. In her soft sexy voice she told me it would be nice if I sent her a check for $100.00 in a package with her clean panties. Asking me if my crotch was still soaking wet she told me that hers definitely was especially after the vibrator. Wondering if I was still turned on she asked me if I wanted to come again. I told her I really couldn't refuse but what did she have in mind? Telling me to get in bed completely naked keeping her wet panties close by she told me she would be giving herself a buzz while I got ready. I tore off of all my clothes jumped on the bed with her panties in hand. My crotch was still caked with and dried semen but I was so horny I didn't even care. My cock was already getting hard again but I didn't touch it waiting instructions from Judi. I gave her a sexy "hello" and I could feel her breathing heavily over the phone enjoying the plateaus phase of another orgasm. Asking me if I was completely naked I told her yes. Telling me that I would have to do everything she ordered or she would hang up the phone Judi asked me if I would obey, I told her I definitely would. In a sexy nasty voice she told me that if I did what she said to the letter I would be blasting my balls off so hard I would have to lay there for a long time to recover. This got me so excited I told her I was more than ready for that for sure. Telling me to get an envelope and my checkbook before we started or she would hang up I quickly obeyed waiting for her instructions. Ordering me to write a check for $200.00 then an addressing envelope put the check inside and seal it and tell her when I was finished. As I wrote the check Judi made me promise that from now on no matter what she told me I would believe it and not be judging her for things she has done in the past or is going to do in the future. Thanking me for the money telling me I she will more than make it up to me as soon. Judi told me that she misses my tongue licking her pussy and if it wasn't for my punishment I would be in bed with her right now between her legs totally intoxicated by her tastes and smells but now instead she has to use her trusty vibrator for pleasure. I was already getting excited and I quickly wrote the check and sealed it inside the envelope. I told her I was finished and she told me to set the envelope aside so I wouldn't get any come all over it. Tossing it on the floor beside the bed was good enough for me as I told her that I was ready for her instructions. Telling me that I was going to have to be a very nasty boy doing everything she said and once I started she was going to give me a confession that would blow my wad. And their soft sexy voice she told me to put my right middle finger in my mouth getting it nice and wet with saliva. I could still taste her pussy juices in my mouth as I started sucking on my finger getting it lubricated. Once it was nice and wet Judi told me to slowly and push it into my and asshole as far as I could fingering my prostate. When we were married Judi had already given me several lessons on finding the prostate gland so it didn't take long and I was pushing my button. When we were together and she usually did it to me using her own finger but this time I didn't have a choice. Once inside Judi asked me how it felt. I told her truthfully I felt quite nasty fingering my butthole yet I was getting quite excited. Cursing she told me that there is nothing nasty about exploring your own body. Ordering me to pick up her panties with my left hand and start masturbating by quickly obeyed slowly stroking myself as Judi's started her confession. Reminding me of the time that I and took a trip to Yosemite with a friend and that I was gone for three days. Telling me I came back thinking that nothing went on. The story was getting interesting and I kept finger fucking my butthole and stroking my cock with her panties getting quite excited. Judi told me that that she found my credit card and went on a shopping spree at the mall buying a complete hookers outfit including a pair of sexy boots. She then got her hair and nails done and went out to lunch with a girlfriend Dana. Describing Dana as a 5ft. 8in. tall black haired brunette with blue eyes with a great body and a huge set of breasts with a dominant nature that a person couldn't say no to Judi told me she was to lonesome to pass up the opportunity to spend time with her. I wondered all these years where the money went when I saw that and credit card was run up. Hearing about Dana and the outfit was turning me on. I continued masturbating slowly hoping that she would tell me the entire story before I came. The girlfriend Dana was a butch lesbian and invited Judi to her apartment. Judi had told me she had experimented with lesbian sex after high school preferring to get her pussy eaten rather servicing the woman. As I masturbated I told myself that I always suspected Judy had a bisexual side. Dana had a Jacuzzi bathtub and invited Judi to take a soaked with her. Judi said even though she suspected getting seduced she agreed to taking a soapy bath with her girlfriend. I could hear the vibrator buzzing on the other side of the phone so I knew Judi was masturbating as well. Judi's said that things got hot rather quickly as Dana pulled Judi breast to breast French kissing her fully on the mouth until she gave in and started kissing back. I could tell Judi was excited because she was talking faster and breathing harder. Judi's said it didn't take long and their hands were all over each other fingering their pussies under the bubbles. It didn't take long and they were taking turns standing in the tub eating each other's pussies. Judi told me that this time with Dana she really enjoyed eating her crotch. Asking me what my feelings were? I told her that she could have confessed to me a long time ago because basically she was exploring her personal sexuality and was not on my business. Judi told me and don't worry she has been exploring all her life thanking me for being open and honest about my opinion. Telling me to keep masturbating slowly so I don't prematurely orgasm because there was a lot more to tell Judi's said that after the bathtub experience they ended up in bed ordering and Chinese food and drinking champagne as they experimented. Judi's said that Dana pinned her down on the bed in the 69 position pushing her pussy into her mouth forcing her to lick it while Dana did the same licking each other to several orgasms. I told Judi I was very close to coming in her panties. Ordering to stop masturbating but keep fingering my asshole Judy said she wanted me to finish the story before I came. Judi asked me if I ever heard of a strapon dildo. Since it was confession time I told her I read all about it in an adult magazine and even saw some pictures of women fucking each other which looked quite exciting. Cursing Judi told me to bring her in that magazine reminding me of all the times she warned me about reading pornography telling me that I deserve a good spanking for that one. Judi's said that she had never seen a strapon before and that afternoon Dana opened her eyes to a new avenue of pleasure. Tell me I can start masturbating again Judi got quite excited explaining how Dana fucked her for the first time with the strapon. I couldn't believe that my own wife had held this secret for so long and now we're both almost coming reminiscing the past. Judi told me that that she had the phone in the crook of her neck because she needed one hand to work the vibrator and the other hand to massage clitoris wishing she had my tongue right now. I think both of us were about to come by Judy continued quite excited telling me that this big beautiful woman strapped on a huge pick dildo then pushed her forcefully over a pile of pillows on the bed. Judi said she felt like a virgin having never been fucked with a dildo before giving her and anxiety attack and a bad case of butterflies as she impatiently waited to be fucked. Telling me that they know was nothing like a stud slowly rubbing lubricating oil into her pussy and on the dildo before she started penetration. Judi reminded me how much she hated intercourse but getting fucked by Dana was something different. Judi's said she could tell by Dana's dominant sexuality she wouldn't take no for an answer. I could hear Judi beginning to breathe a lot heavier and her words started getting interrupted as she started to begin her climax. Because of all the prostate fingering my cock was spewing copious amounts of pre-come and I to was getting close to its shooting another load. Judi's said that once Dana was in place behind her and she could feel the head of the dildo teasing her labia lips open pressing inside she had no choice but to allow the butch to take her without asking. Judi's said that Dana grabbed her hips tightly as she expertly shifted her hips forward thrusting the dildo all the way into her pussy. Just then Judi started to come and she dropped the phone and my cock at the same time started refilling the panties with fresh sperm. I couldn't believe that Judi had done all this behind my back and all I could think of is that she didn't allow me to watch and see all the action as I continued ejaculating. Judi picked up the phone still moaning as the vibrator continued buzzing inside of her pussy. She asked me if I and came yet as I confessed still stroking my cock rubbing fresh come all over it. I told her that was the hottest confession I ever heard and I couldn't help myself from coming. Giggling she admitted either could she. Not wanting to hang up the phone Judi told me that I was good for another orgasm as long as she kept talking. She asked me how her panties looked and I laughed telling her I would have to take them to the dry cleaners twice. Judi told me she would save the rest of the story about Dana for later but now she wanted to get to her most favorite part what she did with the brand new clothes. Asking me if I remembered where she put the vibrator she left at my house told her he was in a drawer next the bed. She told me to get it out and also find my favorite masturbation cream. My face got red with embarrassment because I knew that she knew I frequently masturbated. Grabbing my bottle of oil and the vibrator I told her I was ready. Judi told me my asshole should be more than relaxed to push the vibrator inside so lubricate my asshole and slowly push it in until the tip is on my prostate gland. I told her I'd never had a vibrator and my asshole before so I was a little self conscious. Cursing again Judi warned me that this wasn't a coming out ceremony I was in the privacy of my own home experimenting with a vibrator. She told me that this time she was going to push her vibrator into her own asshole just to let me know that it's possible. Judi told me that she was now over a pile of pillows slowly pushing the vibrator into her butthole and fingering her clit at the same time. Demanding that I would push it in or she would hang up I obeyed and started pushing reminding myself that no one else was watching. Judi The Cockteaser! Anxious to hear if I had obeyed her orders Judi threatened to hang up. I quickly told her that the buzzing vibrator was on its way making Judi squeal. I had to take a deep breath and push outwards as the vibrator spread me open wide causing some pain. I told Judi that it would hurt at first but she told me to continue masturbating to take my mind off the pain. This time I used my hand because panties were soaking wet with sperm. Order me to turn the vibrator on Judi said she was going to start telling her second story. She warned me that the third time I orgasmed with a vibrant directly on my prostate I was going to be screaming as emptied every last drop of sperm. Judi guarantee that I wouldn't be able to get hard for a week after this last orgasm. Judi told me that she had the phone in the pillow next to her and she was busy fucking her butthole with the vibrator turned on fingering her pussy at the same time still thinking about Dana fucking her pussy and then her asshole with the dildo. Phone sex was getting quite exciting especially with Judi confessing her sexual exploits from the past. Telling me buying the outfit worked a perfect. The red "V" necked blouse which opened up showing off her brand new black brassiere that pushed her breasts together exaggerating the size of her tits adding the black miniskirt with no panties as her black thigh length leather boots pointed directly to her crotch. I almost lost it right then and there as I envisioned her dressed that way. I told Judi I was so excited that I wanted to go shopping and by her the same outfit. Giggling she told me to keep stroking and listen. Taking a cab to a downtown hotel Judi's said she was easily able to grab a businessman all alone for the weekend and looking for entertainment. She could tell he was excited about her looks and they went to the bar for a drink to make things look more legitimate. The guy's name was Dave and he sipped a double scotch and Judi had a diet soda. She told me he couldn't keep his eyes off her boobs and she could tell by his crotch that he was already getting hard. Giving him a squeeze when no one was looking She told David she would go up to his room with him for $250.00. She said Dave didn't even blink an eye and that took her hand and quickly led her to his room under the suspicious eyes of the management. Judi's said that there was a fine line at this time about soliciting so the only thing she agreed to was to go to Dave's room and look at it for $250.00. Part of me and was getting angry but I didn't want to show my emotions over the phone because Judi was openly confessing as both of us were masturbating as if everything was OK. In really didn't matter who were already divorced and there was lots of water under the bridge. True sexual confessions were actually sexually stimulating and even though my own x-wife was telling me she was fucking men behind my back I was getting excited. Judi's said once the door was locked Dave took out his wallet and handed her $300.00. Judi said she had been paid for sex before but never had been given that much but she kept a tight lip anyhow. Judi told me that Dave was a real gentleman and the first thing she did was sit on the bed unzipped his pants and suck him hard. Once she saw how big of a cock he had Judi complemented him on his size promising him she was stay two hours allowing him to fuck all he wanted if he took her out to dinner afterwards. Dave actually I agreed to her surprise. I couldn't believe that while I was camping fantasizing about fucking Judi she had a lesbian affair and was hooking on the side. I wondered if she had been seeing other man on the side for cash because remembering back she always had a wallet full of money. I kept buttfucking myself with the vibrator and stroking my cock as my mind went bananas. Judi told me that gave wanted her get naked but keeping her sexy boots on. She helped Dave get naked saying he had a great middle age body slim from playing tennis. Judi estimated his cock being around 9in. long and almost 2in. wide bragging she has accommodated even bigger ones before. I was a little bit taken back because my cock is only 7in. long and a lot slimmer. To make me feel better and Judi noticed my pause reminding me of all the times she sucked my cock telling me was the perfect size for oral sex. After rolling on a condom Judi said that Dave grabbed her tossed her all over the pillows on the bed entering her from behind. Even though he fucked her hard and fast with full strokes Judi said she took everything he had fingering her clitoris at the same time and actually orgasm when he came. Judy said he was a little rough spanking her butt as his thighs pounded her bottom. Judi said she could actually feel his huge balls slapping her pussy lips on every lunge forward. Claiming she could feel his powerful throbbing cock as he climaxed on top of her. Telling me she felt no remorse for having sex for pay behind my back and that she actually enjoyed every minute of it. She liked the hunt, getting the cash and then fucking their horny cocks limp. The vibrator was actually doing a good job getting me excited again even though Judi was confessing some things that in the past would have really hurt my feelings. I'd then expressed to her that we both knew that I couldn't satisfy her sexually and that she was looking for an outlet to explore her sexual needs. Judi agreed but told me that she always felt guilty and that these confessions are actually helping her to get over that guilt and heal the past. I assured her that I totally understood encouraging her to continue her story about Dave. Judi confessed that she was getting quite excited wondering how the vibrator was doing in my butthole. I could hardly answer her question thanking her for getting me out of the box and trying something sexually new. Judi told me that Dana and Dave had two things in common. Dana fucked her from behind to orgasm just like Dave did. For Dave's second orgasm he surprised Judi by fucking her in the ass just like Dana did. Judi said she actually had an orgasm having a powerful man holding her down and fucking her this way. Telling me she definitely earned every last nickel. When Dave pulled out of her asshole he asked Judi if he could give her a spanking. Judi's said she barely got her breath but her mind was still on collecting money so she told him she would let him give her a spanking for another $200.00 thinking he wouldn't pay it. I had always fantasized about spanking Judi because of her hardheaded attitude if I knew I could have done it for only $200.00 I would have paid her long time ago. I was just about ready to come but I wanted to hear about the spanking so I encouraged Judi to keep on talking. Judi said she was quite surprised and really didn't want a total stranger to spank her but she took the money anyway. Sitting on the end of the bed Dave forcefully pulled Judi over his lap and started striking her butt with his powerful right hand. Judi said she started crying out from the painful swats cursing and swearing wiggling all over his lap trying to fight the painful blows. This was exactly how I envisioned spanking Judi as I told myself maybe it was fates way for a perfect stranger to finally get even with a hard headed woman. My cock was rock hard ready to shoot as Judi added more titillating facts of the spanking telling me that Dave spanked her bare bottom until it was flaming red and hurting like hell. He let her fall off his lap with her head between his crotch pushing his erection into her mouth. Holding the back of her head he fucked her face until he came down her throat. Judi said he came so much she was gagging on his come forcing herself to swallow to keep from drowning. Of all the times that Judi sucked me off she never swallowed my come. This was the final trigger that sent me over the edge as I fantasized Judi swallowing my semen as I came. I dropped the phone grabbed my cock shooting a 4ft. squirt of semen all over my bedspread followed by two more 2ft. squirts as my cock continued pulsating in my hand emptying my balls. When I pulled the vibrator from my asshole I came again filling the palm of my hand. Picking up the phone I apologize to Judi who also was in the throes of orgasm crying out as she fingered her pussy and fucked her butthole with the vibrator crying out into the phone. I was so turned on I kept stroking my cock with the spent come in my hand getting it nice and sticky. Both my balls and prostate were painfully throbbing from the orgasm. I told myself that Judi for once told me the truth treating me to the orgasm of my life by confessing the past which turned out to be more orgasmic then hidden pain.