This series of events took place several years, when Craigslist still had their Personal Ads section. Going back to earliest days of becoming sexually active in my late teens, I've always loved giving oral to women. There's something so personal, erotic, and powerful about being able to get my partner off using my tongue.
Over the years, my passion grew and it has become my preferred sexual activity. So much so that I had taken to posting on CL offering to provide oral satisfaction while asking nothing in return. "Your pleasure is also my pleasure" became my motto. While I wasn't overwhelmed with responses, I definitely had some success connecting with women who were interested in just laying back and receiving with no pressure to perform. Many times, I would hear from ladies who were recently divorced or separated and hadn't experienced good (or any) oral in a very long time. I loved it!
One morning, I was checking my email and had a response from my CL ad from a woman named Patricia. Her only initial questions were whether I was for "real" and if I was serious about not requiring she do anything for me. I responded assuring her that I was very real, talented, clean, attractive, and discreet. We exchanged a few more emails and I learned Patricia was 45 years old, originally from Jamaica, divorced, and an executive with an insurance company. She explained she was a very busy woman with a couple of teenagers and didn't have much time or opportunity to date. She loved receiving oral, and was intrigued by the idea of a simple, no hassle arrangement to get off without the entanglements of a relationship. I suggested she give me a try and if she was impressed, maybe we could make it a regular thing. Patricia asked for my cellphone number and told me she'd think it over and text me if she wanted to move forward.
The following Tuesday morning, I received a text from a number not in my contact list. It simply read, "Eddie?" Grinning and hoping it might be Patricia, I replied that it was indeed Eddie.
"This is Patricia. Are you available at lunch time today?"
I should mention that I was working second shift at that time so I didn't go to work until 3:30pm. Mornings and early afternoons were prime time for me. I advised her that I was free and she texted me an address and told me she had a few rules. The first was that I was to remained clothed the entire time. The second was that she would leave the garage door open. I should park a couple houses away, and then enter through the door inside the garage. She would leave it unlocked and her bedroom was just to left after I entered. Third rule was that she would be on lunch hour from work and when she told me she'd had enough and needed to go, I would agree to immediately leave. I texted her back to say I was good with all of that and would be there at 12:15 sharp.
I had a general idea of what she looked like as she shared a couple of pics of her in business attire (head/face cropped out). She appeared to be petite and in decent physical condition. I was excited to unpackage her and dive in. I arrived 15 minutes early just to make sure I was able to locate her home. It was in a fairly upscale subdevelopment and the garage door was closed at the address she gave me. My heart sank a bit wondering if the whole interaction was someone messing with me. But I also knew she was coming home on her lunch hour so maybe she just hadn't arrived yet? I drove back out the main road and headed to a convenience store to kill a little time. At 12:10, I drove back down her street and sure enough, the garage door was now open! As instructed, I parked on the street two houses down and casually walked back the house, into the garage, and turned to knob on the door. As I pushed it open, I heard a voice call out, "please close the garage door." I tapped the button on the wall and the garage door descended. I stepped inside and glanced to left.
I could see Patricia sitting on the edge of the bed. She was wearing a white blouse and knee length navy skirt. Her heels were laying the floor at her feet. I stepped into the bedroom and she stood. It was the first time I'd seen her face. She was cute, about 5' tall and in decent physical condition. I told her it was great to finally meet her and thanked her inviting me over. She nodded, smiled, and spoke matter of factly.
"I don't have a lot of time. I'm trusting your promise that you are discreet?"
I assured her, "100%!" And with that, she unzipped her skirt and let it drop to the floor. I still remember that first meeting vividly. She was wearing a pair of yellow lace panties. She laid back on the bed, lifted her hips, slid them down, and kicked them to the side. I climbed onto the foot of the bed and started at her calf, slowly kissing and licking my way up. As a reached her thigh, I pulled my lips away and lowered myself to do the same on the other leg. Patricia was polite but firm, "I don't have a lot of time and I don't need much to get warmed up."
I looked up, nodded my understanding and began lowering my mouth to her pussy. It was compact and she was completely shaved. I pressed my thumbs against the outer lips and admired the contrast between her dark skin and the glistening pink they revealed as I spread them. She was right, she was already very wet. I started by pressing my tongue into her wet hole, easing it in and out several times. I then slid my tongue slowly upwards until I reached her clit. Patricia shuddered and put her hands on my head.
"Put a finger inside me," she instructed. Over the years I've come to learn that there's no one technique for giving good oral to a woman. Everyone is a little different so it's important to read body clues, pay attention to what's getting a reaction. And there's nothing better than a woman who's willing to tell you what she likes!
I pushed my middle finger into her taut slick pussy and concentrated on her clit with my tongue. "Just like that!," she encouraged me as she steadily rocked her hips into my face. I could feel the muscles of her pussy tighten even more and her breathing was turning to pants. Her fingers dug into my temples and with a sudden violent buck of her hips, she orgasmed! As she began to twist her hips, I fought to keep my finger inside her and my lips on her clit. After a few more spasms, she pushed my head away. We lay there in silence for a few moments and then I began licking around her outer lips again. Patricia lowered her hand over her pussy and said, "I can't cum again right away. I'm good. You can go. I need to get dressed and go back to work."
I stood, told her I really enjoyed it, and hoped she had too. I exited through the door, opened the garage, and walked out to my car. The entire encounter had lasted less than 10 minutes, but I hoped she was impressed enough that it wouldn't be a one time thing. I drove back my house, dropped my jeans and jerked off reliving it in mind!
Around 4:00 that afternoon, I got a text from Patricia.
"Are you available at the same time on Thursday?" A huge smile spread across my face as I answered that I would make sure I was! When I entered the house on Thursday, she was already undressed and lying on the bed. This time she was completely naked (she hadn't removed her blouse the first time). She had nice breasts, probably B cups with small nipples. They fit her petite body well. We didn't exchange any words, I knew what she wanted and expected. My mouth went immediately to her wet pussy. As I began to lick, she spoke, "play with my nipples." My hands slid up her body and I pressed both palms to her breasts and began rubbing lightly but steadily. Not quite what she wanted and she wasn't shy about clarifying.
"Pinch them!" I obeyed, applying pressure with my thumbs and forefinger as my tongue darted steadily over clit. "Good...good...yes." Again, she grabbed my temples and began grinding into my face. I continued pinching her left nipple but dropped my right hand between her legs. This time I pushed two fingers into her sopping pussy and began working them steadily. It couldn't have been more than 45 seconds until she was bucking and twisting in orgasm. Again, we lay in silence for a minute or so as she recovered and she thanked me and said I could go.
This became our routine every Tuesday and Thursday over the next 6 weeks. I'd show up to her naked in bed, get her off, she'd get dressed as I left, and she'd head back to work as I headed home. It was an awesome deal for a guy who loves eating pussy!
Then one Tuesday, I walked into Patricia's bedroom to find her sitting on the bed fully dressed and she said, "I need to tell you something." She explained that a longtime friend and coworker had asked Patricia why she was seemed to be in such a good lately. Patricia confessed to Marie that she'd been getting some great oral sex lately and it was improving her mood and energy. Marie expressed her envy and told Patricia she hadn't had any sex for nearly two years since her divorce. Marie was 60 years old and not comfortable with the new online dating world. She was also an upper level manager, very busy and just hadn't met anyone new. Patricia confessed the details of our arrangement to her, expecting Marie to be shocked. Instead, Marie was intrigued and had several questions. Patricia promised she hadn't given Marie any specific information about me, and wouldn't do so without my permission. She apologized and hoped I wasn't upset that she had shared. Conversely, I was flattered and turned on! Before I could ask the first question that popped into my head, Patricia asked me if I might be interested in talking to Marie. I didn't want to act overly excited, but said it sounded interesting. Patricia asked if it was okay to tell Marie my first name and show her a picture of me. I said that was cool and asked if she had a pic of Marie that I could see. Patricia said, "I'll see if she's really interested and if she is, we'll go from there."
Patricia looked at her watch and scrunched her face. I can be a few minutes late from lunch. She hiked up her dress, pulled her panties to the side, and sat back on the bed. I dropped to my knees and got to work. Three minutes later she had cum and we were both on our way. The next morning, I got a text from Patricia at 11:30am asking if I was busy. I told her I wasn't and she asked if I could get over to her house at the usual time. Wednesday wasn't our usual day, but I wasn't going to turn down an opportunity. As I walked into the house, I heard conversation. Patricia called out, "in the kitchen."
I realized I'd never been the kitchen, but I turned right this time and followed the voices. I entered to Patricia motioning towards me, "Marie, this is Eddie. Eddie, Marie wanted to meet you. I trust that's alright?" I smiled and responded, "Of course! It's great to meet you, Marie." She stood and extended her hand, clearly uncomfortable. Marie was much taller than Patricia and more full bodied. Definitely thicker and curvier. Her dark hair was in a bun and she was dressed impeccably in slacks, a blazer and a floral blouse. Patricia asked Marie if she wanted to speak with me alone or wanted her to stay. Marie pondered the question and then informed Patricia she was good. Patricia excused herself saying was headed back to office and asked Marie to lock up when she left. Marie and I sat across the table from one another and she nervously explained that Patricia had told her about our arrangement and said that I was very good at what I do. I smiled and said it was a passion of mine. She asked why I didn't expect a woman to do anything for me in return, and I explained that I wouldn't refuse but that I didn't require it. My biggest thrill is giving pleasure.
Marie sheepishly asked, "could you find a women like me attractive enough to do that? I'm much older than you and I'm definitely not in the kind of shape Patricia is." I assured her that I found all types of women attractive and that included her. Marie was looking down at the table now, "you should know, it's been a really long time since anyone's done anything, let alone THAT, to me."
I offered, "seems like it's time you got back on the horse then?" Marie looked up and made eye contact. She seemed to like that answer. "So, if you did that and afterwards I were in the mood to do the same thing to you, you'd be alright with that?"
I smiled broadly, "You're the boss! Whatever you want." Marie confessed that she also enjoyed giving oral. She asked if she could think about and let me know. I gave her my # and said she could reach out anytime. The following day was my regular Thursday meet-up with Patricia. I arrived and she was naked and ready to go. I dove right in and within minutes she was screaming in orgasm. As she lay recovering, I started to ask if she'd spoken with Marie.
Patricia cut me short, "I introduced you because she's a friend and I think she could use your help. But I don't want any of us comparing notes or talking about one another. If you two make an arrangement, that's fine. As long as it doesn't interfere with our Tuesdays and Thursdays. Good?"
"Got it!"
Several days passed without any word from Marie and I started to think she'd decided she couldn't follow through. I was bummed because I'd never had the pleasure of a woman in her 60's and I was eager to help her break that lengthy drought. On Sunday evening, I received a text from an unknown number.
"Eddie, if I meet you, nobody can know! I mean nobody." Although she didn't say so, it was clearly Marie. I reassured her of my discretion and recommended she talk to Patricia. Marie responded that she wasn't going to say anything to Patricia about it. They had agreed there would be no more discussion of me between them regardless of what happened. Marie asked me if I could come to her home on Wednesday at lunchtime. I agreed and she sent me an address. She explained there was a bike/walking trail that ran along the back of her property. She told me she'd leave the sliding glass door into the kitchen unlocked. I should park on the next block, walk down the trail and enter through the back door. After leaving Patricia's on Tuesday, I drove to Marie's neighborhood to make sure I could navigate getting to her place as instructed. After assuring myself I had the route, I headed home. I returned Wednesday strolling down the trail. Checking to make sure nobody else was around, I walked through Marie's yard and pulled the sliding door open.
"I can't believe I'm doing this!'" Marie's voice came from the family room off the kitchen. I turned to find her sitting on the couch wearing a full length pink robe. "Come sit down." I sat at the opposite end of the couch as she toyed with belt of her robe. Without making eye contact, she asked me to follow her. I watched her large ass sway under the robe as we walked down the hall towards her bedroom. She stopped when she reached the bed and turned towards me, "how do we do this?" She was still fiddling with the belt of her robe and took it from her hands. Untying it, I let it fall and the robe opened partially. She was completely nude under the robe and I could immediately tell her breasts were larger than I'd imagined. She was shaking a bit as I opened the robe and pushed it over her shoulders. Her breasts sagged some but looked delicious with huge pale areoles and nipples. Her stomach, hips had thighs had some girth but she definitely looked good. Very womanly! I ran my fingertips down the front of her body, starting at her shoulders and ending at her lower stomach. As I teased the soft area just above her pussy, she whispered, "I shaved it all. I hear that's popular now."
I grinned and replied, "it's all good. Whatever works for you." I gently pushed her back onto the bed and told her to relax. I stopped to ask how soon she had to be back to work and she told me she'd taken the afternoon off. Perfect, no need to rush like with Patricia. I started by sucking one of her nipples while rolling the other. She immediately responded and began squirming. I licked and kissed back and forth between them while pressing my thigh against her bare pussy. I could soon feel her wetness and heat through my jeans. I began kissing my way down her stomach while sliding my hands under her big ass. She was already breathing heavily when my mouth reached her freshly shaven pubic area. I pulled back a moment to get a good look at her pussy. It was swollen, thick meaty lips spread, and pulsing. She had a very large clit that extended a good half inch beyond it's hood. I blew lightly on it on she shuddered, "Please! It's been so long."
I closed my lips over her clit and flicked my tongue twice. As I started to take a third lick, she screamed, her body contorted, and she began shaking as she came. I held my mouth tightly against her pussy and rode it out with her. Her orgasm lasted nearly a full minute. As her legs collapsed over my shoulders, she immediately began apologizing for cumming so quickly.
"It's just been such a long time since I've felt anything like that..." I interrupted her laughing, "Marie, that was awesome. Don't be sorry. We can start all over as many times as you'd like."
"Okay, but first can I, ummm, can you, ahhh, maybe take off your pants?" I stood, pulled off my t-shirt and undid my jeans. Marie sat up and watched intently as I slid my jeans and boxer briefs down together. She gasped audibly as my stiff cock popped free. She slid off the bed and onto her knees.
"Look how hard you are. Do you know how long it's been since I've touched one of these. Even longer since I've touched one this hard!" She handled my cock very delicately at first, almost like she was afraid to break it. After running her fingers along the shaft several times, she looked up at me, "can I...taste it?"
The difference in demeanor between Marie and Patricia was stark, but both very hot in their own way.
Marie took my cock into her mouth. She may not have given head in awhile, but she clearly knew what she was doing. I mumbled that if she kept it up, it would be my turn to apologize for cumming so fast. She pulled her mouth from my dick long enough to smile and stick her tongue out at me. Then she went right back to work. Stroking my shaft with her right hand, swirling her tongue around the head, and caressing my balls with her left hand. It wasn't long before I felt the pressure building. My hips were moving involuntary and I groaned, "I'm close." Marie removed her mouth and began stroking the full length of my shaft and head faster.
"I want to see you cum. Shoot it on me, Eddie." That pushed me over the edge and exploded, spurting my load on her chin, neck, and huge swaying titties. "Oh God, that's so hot," she moaned as my cum ran down her chest. Once I composed myself, I laid Marie back out, licking and fingering her to 4 more orgasms. I barely made it home to get cleaned up and to work on time.
I continued to meet Patricia just about every Tuesday and Thursday for a couple more months until school was out for the Summer. It became tougher to find times that worked and we eventually lost touch. I got to meet up with Marie 3 more times over the following month. The experience seem to give her a lot more confidence and she ended up meeting a guy and getting into a relationship. She assured me that if she found herself single again, she'd be in touch. I never heard from her again.
I have to say, I really miss Craigslist!
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