Red Headed Delight Pt 01

Twenty years ago, I used craigslist to post anonymous ads looking for older women interested in ongoing friends-with-benefits relationships. I was in my late twenties and had been exploring age-dynamic relationships through most of my sexual life, with both women and men.

Sometimes even together. I was attracted to the 'kink' of the age gap, but also found that those 15-20 years my senior, especially women, were more confident and knowledgeable about what they wanted in a sexual relationship.

Bubbles responded to one of my ads in early summer, so early it was still, technically, spring. She was light on details of her life, and wasn't big on sharing photos of herself either, which is how I ended up calling her 'Bubbles' throughout our relationship. The email she used to respond to my ad was bblgmgurl, and it wouldn't be until our first meeting in person that I would learn her real name was Denise. Which was also my sister's name, so I was happy to keep using a pet name with her.

Bubbles and I exchanged a lot of emails over the course of our first three weeks chatting, usually with more than one reaponse a day from each of us. Our communications started out very vanilla as we discussed our lives and what each of us hoped to receive from a relationship together, but soon turned to very lurid fantasies of what we'd like to do with the other. As an exhibitionist, I was very happy to snap and send photos of myself for her to lust over, while the most revealing thing she ever shared with me was a green, thong-covered shot of her ass.

Bubbles was hesitant to meet in person, citing a string of 'no-shows' she had experienced over the last few years which had left her a little jaded; she also was open and honest about her perception that I was 'fucking with her' and not serious about meeting. She had divorced her husband a few years ago and found dating again to be difficult and challenging.

But after a couple weeks of chatting, I left town for a week to attend an annual family gathering, and our seductive chat ratchetted up considerably, our emails leaving me with a near permanent hard-on throughout my vacation. I was lusting after her hard and made concrete plans to meet her in person after work, the Monday I returned from my trip. I proposed meeting up for lunch on Sunday -- mere hours after I returned -- but she had other plans and we settled on Monday night.

Monday was excruciating for me at work: trying to play catch-up from a week out of office while my mind was fully focused on my plans that evening. I agreed to drive the 30 minutes north to where she lived, agreeing to call her when I was on the way, and she'd confirm a meeting place for us. I didn't receive an email from her all day, and my concerns were heightened when the first call I placed to her, as I was leaving the office, went directly to voicemail. Was she going to no-show on me after all her concerns about me standing her up?? But I kept driving and 10 minutes later when I called again, she picked up in a very hushed tone on the first ring, telling me she was still at work and would call me back in 5 minutes.

When she called back, she asked me to meet her in the back section of the parking lot of a well-known retailer and hung up before I could even confirm the location with her. But when I arrived, I spotted the purple Trans Am she had described to me previously sitting alone in the back of the parking lot. I pulled up next to her and asked if she wanted to grab a drink or something, but she declined and instead asked me to come sit in her car and talk for a bit.

I exited my car and joined her in hers, sitting in the front passenger seat. The photos she sent me did her no justice, and I was quick to inform her that I thought so. She demurred, and said I was obviously lying, but I took her right hand in mine and placed it on my erect cock, then looked back into her eyes and told her how I had been thinking about her all day. She squeezed my cock through my pants and gave a low volume, "oh my" as she started running her hand along the full length, her eyes watching her hand slide along my erection. I tapped her chin with my right hand and leaned in for a kiss, soft at first but soon my tongue penetrating past her lips as I brought my right hand around to her neck and pulled her in closer, our kiss building in passion and she took her hand off my hard cock and brought it to my cheek.

"Whew' she responded as I ended the kiss, eliciting a smile from my lips. "That was nice," she added.

"I've been thinking about kissing you for a long time," I injected, bringing her lips back to mine for another quick kiss.

"There are so many places on your body I want to put my lips," I said to her as our kiss ended, looking her squarely in her bright emerald-colored eyes.

Bubbles didn't respond but shifted her position in her seat to rest against the car door and sit facing me from the side. Her long, curly red hair flowed well past her shoulders, and she wore a modest black t-shirt and slacks. I leaned in for another kiss, but she moved her head away and took my hands in hers, letting us sit there together staring into each other's eyes as silence filled the car again.

"What do you want to do now?" I asked, breaking the quiet.

"Let's go grab a drink" she declared, starting up her car. "You want to follow me over to the bar in your car?" she asked.

"Ummm, sure" I stammered, confused by the changing events. "Where are we headed?" I asked for clarification.

"There's a little bar just down the road here called, 'Dewey's'. Meet over there, you can follow me over" she added, reaching down into her purse and pulling out a pack of Virginia Slims. I opened the car door on my side and slide out, walking around the front of the car as I watched her light up the cigarette. I poked my head in and asked slyly, "So this is how you're going to ditch me?" laughing a bit at the end.

"Maybe." she confirmed. "Do you not want to get a drink?"

"Oh, I'm happy to get a drink" I responded, poking my head inside her car from the open window. "I'd rather take you home and get your naked though" I added, leaning in for a kiss that she accepted, her cigarette held between two fingers against my cheek.

"Let's go get a drink first" she declared, pushing me away slightly and putting the car into reverse. She pulled out of the spot quickly and raced away as I stood rooted to the spot next to my car.

I was sure this was all on put-on, but as I pulled into Dewey's parking lot a couple minutes later, I noticed her empty purple Trans Am and parked next to it. I walked inside and found her returning from the bar with a pitcher of beer in one and two empty glasses in the other, nodding towards a high-top table nearer to the pool tables. She set the beer down and headed back to the bar, retrieving two shots of brown liquor, and setting them down on the table, pushing one towards me while she held up the second. Standing next to her, I realized I was about half a foot taller than her which we must not have discussed during our chats.

"To tonight" she declared, clinking glasses with me and throwing back the shot before I had time to think clearly. "Wooo," she shouted, before picking up the pitcher and pouring us each a beer, both of us quickly chasing the shot with a large gulp of beer. I topped off our glasses as she came around the table and grasped my arm, pulling me over to the nearest pool table and asking me to, "rack em up."

"I have to be honest with you," I told her as she started to let go of my arm, "I am a terrible pool player. Like I'm not going to get one ball in bad."

She smiled in return and whispered close to my ear, "oh, this will be fun for me then" and gave me a quick kiss on the cheek before walking towards the far wall where cue sticks were hung on the wall. "Rack em up and I'll break for us," she declared, chalking up her chosen stick as she walked back towards me.

And I'm sure she had a lot of fun because on the first game, she ran the entire table before I even got a turn to go once. And then she killed me in the second game, which caused me to buy the second pitcher of beer. And indeed, she won the third game even though I successfully managed to pocket two balls in that game.

As the games continued, and the drinks flowed, our bodies got closer together. She'd squeeze my ass when she walked by me or stand right in front of my and wiggle her ass into my crotch. For someone who hadn't had a lot of sex over the last few years, she knew how to tease a man.

About midway through our fourth game, activity in the bar started picking up and I realized we'd probably have to surrender our table pretty soon to other patrons. As we finished, a couple of guys approached and asked for winner for the next game, but Bubbles replied that wouldn't be necessary and we handed over the table to them.

"What now?" I asked her as we returned to our table. She finished the remains of her beer in one quick gulp and putting the glass back on the table, asked, "Well I have a pool table at home, so we can continue this party there if you want?"

"Well of course you kicked my ass, you have a table at home!" I declared in shock outrage, as if I stood any chance at beating her in pool. "But yes, I'd love to go back to your place" and gave her a big smile.

We left the bar holding hands and walked out to our cars together; we agreed I'd stop and get a case of beer on the way to her house, and she gave me her address before we departed with a long, sensual kiss, my hands grasping her plump ass cheeks for the first time. Bubbles was slightly pear shaped and had a noticeable ass I was aching to touch.

I stopped at the liquor store to grab some beer, and popped into the adjacent pharmacy to grab a box of condoms, and was pulling up out front of her house within 15 minutes of our separation, her purple Trans Am sitting in the drivewat and the front door standing open behind the screen door. I poked my head in and shouted out a loud, "hello" as I entered the living room, catching the screen door behind me so it didn't slam shut.

Bubbles appeared from around the corner of the kitchen, having removed her jeans and appearing in just her black t-shirt and a green thong that I thought matched her eyes well. I wondered if it was the same green thong from the photo she sent me.

"Wow, look at you" I said as she came over, threw her arms over my head and initiated a long, sensual kiss at the open door, in full view of the neighborhood. I wanted to touch her so badly, but with the case of beer in my hand, I was stuck and soon pinned up against the wall as she continued her kiss more aggressively. When she broke it off, she thanked me for stopping for the case of beer and took it out of my hands, turning towards the kitchen as I followed behind, admiring her naked ass cheeks and the cute green thong she was wearing.

"I love your thong," I said to her as I closed the space between us and grabbed her ass cheeks in both of my hands, causing her to give a startled jump before relaxing and letting my squeeze her plump cheeks.

"Thanks," she responded, before adding, "do you want a beer?" as she opened the case and removed two cans, then putting the remainder of the box in her kitchen fridge. I took the opening as she turned her back to me and pinned her against the fridge, my lips quickly finding hers awaiting my kiss, my right hand immediately reaching up and grasping her left breast in my hand for the first time. As she moaned into the kiss, I picked up the intensity of my kissing, before removing my hand from her breast and bringing it down to her sex, cupping it in my hand and squeezing slightly, feeling heat emanate through the clothing. She swiped my hand away from her crotch, and broke off our kiss, squeezing past me and exiting the kitchen after grabbing her can of beer.

"Follow me" she instructed, and I did, following in-step with her down the hallway as she pulled her black t-shirt over her head, then reached around and unclasped the black bra she was wearing, leaving each item strewn on the carpeted floor as she continued into her bedroom.

She walked a few steps into her room before turning to me, exposing her nearly naked body to me for the first time. I was taken away by how beautiful her body was: her long, curly red hair extending past her b, not quite c, cup breasts that still held their weight and shape but were accented by delicious looking long nipples, 3" erect she had told me over email. I couldn't contain myself and brought a hand to each breast, feeling their shape and weight in my hands as I groped her, leaned my head in and brought my mouth down to her left nipple, sucking it into my mouth, running my tongue along it to extend its length before dragging my teeth over it and letting it escape from my mouth.

She moaned in encouragement, bringing her left hand to my head to invite me in for more as I shifted my oral attention to her right breast and began to kiss, suck and nibble on the flesh parts before devoting extra attention to her nipple. She had described her long nipples to me in detail, and I had fantasized about this moment when I'd finally be free to explore them with my hands and tongue. She told me they were extra sensitive and the shortened breaths and audible moans indicated to me that was certainly true.

I lifted my mouth off her breast and brought my lips to hers, my right hand automatically finding her left breast again as she raised up on her toes to get closer to me, her hands now running through my hair as my right hand left her breast and moved to her ass, both of my hands kneading her ass checks as we continued our tongue dance.

Needing a breath I broke free from her lips, a disappointed sigh leaving her lips that was quickly replaced by light moans as I started to kiss down her neck and shoulders, leaving little nibbles back along her collarbone as I brought my lips to hers quickly for one last kiss, before I started sliding down her body with kisses, crotched in a catcher's position as I placed light kisses along the slight pouch of her stomach. She brought her hands down to cover, a little bashful of her midsection, but I knocked her hand away and slid all the way down to my knees, her green thong the only thing keeping me from her most intimate spot.

I place my face against the green cloth and breathed in her intimate scent as her hands found their way to the back of my head again and my fingers started pulling down the remaining fabric keeping me from her full nakedness. As I tugged on the right side of her thong, she shifted a bit and gave me the freedom to yank them half-way down her thighs from the other side, exposing a very full, bright red bush to my hungry eyes.

As she helped me rid herself of her thong, I couldn't take my eyes off her pussy, and as she completed the task and sat on the edge of the bed, I spread open her legs and started a trail of kisses along her inner thigh, stopping to breath in her excited pussy, and run my tongue through her full bush.

"I love how much hair you have down here," I said to her, looking up as I ran two of my fingers through her hair. "I've never been with a redheaded woman before, and this is more than I could dream of," I added after she didn't respond.

"Well, I wasn't going to shave it for someone who probably wasn't going to show up," she stated, returning to that line.

"Noooo" I said, dragging out the word, "I fucking love your pussy, I don't want you to ever shave this off."

"OK," she said curtly, ending our minor conversation. Which was fine, because I used the two fingers playing with her pubic hair to part her lips and I took my first taste of Bubbles' sweetness, running my tongue starting from her very wet vaginal opening up her slit and over her large, engorged clitoris.

Like her nipples, Bubbles had a clit that was larger than most women I'd been with, and my tongue was immediately drawn to it; after that initial pass, I took another full pass from her opening to her clit, then a third before I began to focus on her clit, circling it with my tongue, sucking it into my mouth before repeating the circular passes from the other direction.

For someone who was quite demure over email, Bubbles found her voice in her aroused state, moaning and grunting loudly, audibly directing me which spots I should focus on, begging me to return when I pulled off to drive up the tension.

Her first orgasm caught me by surprise as there wasn't a noticeable change in her moans or language, just a couple quick thrusts of her hips against my tongue before she violently started convulsing against the bed, her hands grasping either side of my head and squeezing it firmly in place as her thighs tightened against my head as well, pinning my face against her pussy as she continued to hump my face from her bottom position.

She relaxed her grip as her orgasm waned, but I wasn't done with her pussy by any means. Bringing her to orgasm gave me the freedom to explore more of her pussy with my tongue, opening her lips wide and running my tongue along the inside of her, avoiding her sensitive clit for the moment. I took time to run my tongue through her pubic hair and suck out whatever spit or wetness lingered, before diving my tongue back into her pussy.

Bubbles writhed on the bed above me, her grunting becoming more primal and instinctual as I resumed my focus on bringing her to orgasm. As she shifted higher on the bed, I was able to rise off my knees and partially join her, placing my right knee on the bed while my left leg stayed extended on the floor. I pushed her legs up and spread then open; she grabbed the backs of her knees to keep herself in that position.

I looked down at my prize and could see her engorged clit standing out, begging my tongue to find it, which I quickly did. Three, four passes over her clit and Bubbles was convulsing on the bed again, screaming out, "I'm gonna come, I'm gonna come" as another orgasm washed through her body.

As she recovered on the bed, I stood up and removed my shoes, pants and shirt and joined her on the bed in just my boxer briefs. I slide up next to her, bringing my left hand to her face to turn her to face me, bringing my pussy-coated lips to hers and initiating a slower, more passionate kiss as my left hand left her face and quickly found her right breast, even more quickly finding her elongated nipple that my fingers began squeezing and extending it from base to tip. The orgasms, the kiss, playing with her aroused nipples left Bubbles sensitive to my touch, and as our kiss continued, I felt her bring her right hand down to her pussy and start to vigorously rub her clit, breaking away from the kiss as she couldn't contain her moans of pleasure any longer.

"Let me help you with that," I offered, starting to slide back down her body, but she grabbed me with her left hand to stop me.

"No, keep kissing me and playing with my nipple" she barely got out as her mouth sought out mine, the kiss lasting just a moment as she closed her mouth tightly then emoted a long, "shiiiiiiiiiiiiit" as a very powerful orgasm ripped through her. I grabbed her tight to me as she continued to rub her clit over the crest of her orgasm before collapsing like a starfish against the bed as it passed.

"That was amazing" I said to her, placing little kissed down her chest, slowly licking around her left nipple.

"You're telling me,' she replied, as she reached out her left hand first to my thigh, then to grip my hard cock.

"Mmm, thanks for taking your clothes off," she said to me as she turned her body towards me, opening her eyes and looking into mine, before closing them again and leaning in for another kiss.

She rolled on top of me as our kiss continued, allowing my hands to run along her back and grab her plump ass. I gave it a small smack with my right hand which caused her to moan into my kiss.