* Preface – So I’ve been a longtime lurker in this sub. I have swayed back and forth on sharing my experiences, but finally decided to start. Not only to share, but also to solidify my memories and spend some time revisiting them in detail. I was only in long-term relationships in HS and Uni. Then, I discovered adult dating sites right as they hit their stride in the early 2000s, and it certainly led to many wonderful memories and friendships.
* I’ve seen a few things that turn people off in this sub, so I’ll be clear here: names will be changed, I’m always safe but mention of protection is left out unless it was important to that encounter, and there’s no reason to embellish as reality was fantasy enough for me. I will break stories apart for brevity’s sake, but never hold follow-up parts hostage just for attention and feedback. They’re coming.
*Season 1 – Lani*
I had just started my final year of undergrad and was living on my own after a serious breakup. Being single for the first time in almost 6 years and having money from great part-time work and lots of free time led to lots of sex on the mind :). I came across an adult dating website on a porn site and despite being doubtful, had nothing to lose being single. I quickly had luck talking to, and meeting, a few women that quickly developed into a real thirst for that wonderful rush of being intimate with someone you’ve only known for the span of a meal or a coffee.
A few days of chatting online to create tension and anticipation all released in person was such a delicious thrill. If it matters, I am white, 6′ and was a little chubby when younger. However, I was in quite good shape from the end of high school on, yet I didn’t realize it… always thinking of myself as the undesirable guy. This led to a real humility that I think women appreciated and kept me modest. I was also a photographer and writer, so according to the women, my profile and photos really stood out as polished.
Lani wasn’t the first, but she was the first that developed into a real FWB situation that lasted. So I’ll start with her.
One thing that immediately became clear when I started getting replies on the site, was that as a young guy, I seemed to be attracting women in their 30s and 40s way more than the 20-year-olds. I was fine with this and it was a rush after only having women my age prior.
Lani was 46 and from Hawaii. We chatted for a couple of weeks before meeting. She was married but they were beginning an open relationship (later to be divorced) and I seemed to be the first experiment. She clearly was eager while never seeming desperate. This was such a turn on. There were no games. She said what she liked. She said she liked me. She said it often and yet stayed safe about the whole situation and never rushed. She liked the anticipation too. An appreciation for drawing out a moment.
We decided to meet at a hotel and spend the night together if things went well. She lived about an hour away from me, so there I was, parking at a hotel in a big new city I hadn’t been to before. I sat down in the lobby, awaiting her text or appearance.
I wasn’t there long enough to relax because in she walked, way overdressed for the hotel, in a short, black, sparkly dress which would have been appropriate for a formal gathering and not an interstate-accessible Hilton. She was mocha-skinned and about 5’9″, quite tall in black heels, with long curly hair. She had enormous eyes and they had locked onto me well before I had turned my head to see her enter. Lani (Leilani), used to be a dancer and had maintained the strength and stature despite being twice my age. Her breasts were small but shared online photos had shown me gloriously thick, dark nipples.
A smile of a shared secret, which seemed to evaporate 15 years from her, creased her lips as she motioned for me to stay seated. She walked past me to the front desk and checked in, getting the key. She walked back past me and I followed, too eager to give her a berth. I was a tad nervous because of her seeming confidence. She looked stunning and I could already smell her flowery scent. It was plumeria, which is a white Hawaiian flower with a yellow center that’s an intoxicating smell if you’re familiar. Looking back, I’m sure everyone else in the lobby knew exactly what was going on, but in the moment, I was sure we were so discrete and cool.
There were no lights in the parking lot just outside the lobby and all I could see was the gleam from her eyes and glossy lips, exposing a giant, uncontained smile as she was waiting for me to close the final few feet between us. Her wide eyes got impossibly wider as she grinned and opened her arms to me. Hands slipped up to each of our faces as we seemed to symmetrically embrace and cradle the other’s neck as we just dove straight in for a kiss. Her smell wrapped around me. I was in a passionate embrace with a woman 25+ years older than myself. The heat of her body pressed up against mine on a warm desert night. Her fingers traced back and forth along my jaw and her lips were slick and full. Her hips jutted up against mine, the same height with her heels, as if locked in with magnets, squishing away any possible space between us. My excitement was outlined clearly against my jeans, standing straight up towards my stomach, and peeking out the top of the hem. She was hungry.
I wasn’t checking my watch, but I’m sure it lasted a full two minutes before we let go. I jokingly said “Hi, nice to meet you,” and she slapped my shoulder in jest. It was instantly comfortable without losing the edge of newness and taboo because of the age gap and her being married and just meeting each other. There was no small talk. We felt what we wanted and saw it blatantly mirrored in each other’s faces. The air felt electric with excitement. I’d had glimpses of this a couple of times in the past month with other ‘dates’ but this was on an entirely other level. We both knew what would happen next and not talking about it was achingly good.
We went up to the 2nd floor using the stairs and I followed, getting a wonderful view of silky smooth thighs disappearing beneath the jagged edge of the dress. We entered the room and only turned on a bathroom light with the door almost closed, so the room stayed dim and mysterious. We stood there for a moment, both barely highlighted from the only sliver of light in the room. She had brought a bag and pulled out a fruit and cheese platter of all things. She said she wanted to have snacks if we got enough exercise. Plus, she’d always wanted to feed someone grapes while naked.
It was such an endearing and unique confession. I had already been hard since before getting out of my car, but now I was pulsing. It’s difficult to describe but there was such an instant connection and familiarity with Lani. There was never a moment of feeling rushed or nervous of what comes next. We settled into what we knew would be a long, sleepless night of sound and sweat.
She was standing against the edge of the bed and I stood right up against her, my hand at her sides. We paused our cute banter to kiss again while my fingers started to gather up the material of her dress in my palms, slowly raising it to her hips. She was wearing black, lacy thigh highs and a garter belt, which I told her was my absolute favorite. She surprised me though, saying she had already taken off the matching black panties in the car.
I cradled the bunched-up dress against my forearms and her waist, as my hands snaked across her naked hips, angling down to her center, to test her claim. My fingers met hair a few days past the point of being scratchy, maybe a half-inch long and uniformly even across her mound. There was none along her lips and below though, giving my fingertips a slippery smooth slide across the edge of her pussy. I was loving how confident she was. There was no hesitation in her. She moaned into my kiss and my mouth broke into a grin against hers. It was on.
Pent up excitement exploded from both of us as clothes were stripped and I pushed her back, falling onto the bed. She tried to pull me on top of her, but there was no where I was going except on my knees. I love, LOVE, going down on a woman and if I had my way, I’d start there before even a kiss. I was dying to feel her thighs against my cheeks and her hands in my hair as I explored her, seeing what sounds I could illicit from her lips as I kissed here and licked there. Test driving her feast of sex, proud of each spasm and twitch her body responded with. I took my time and I built her up to a point of no return. She whimpered nonstop as I rolled her clit between my lips. My tongue cradled her bud as I sucked on her, adding pressure to the mix.
When her hips were in a state of constant slight shaking, I brought a hand up to my chin and started to massage the base of her opening with the flat of my thumb. Rotating against her tiny chasm between pussy and ass. Everything was so slippery, I’d occasionally let the tip of my thumb slide into either hole, waxing and waning between. Meanwhile my mouth was centered on her clit, my warm tongue enveloping it and rocking back and forth, not pushing for an orgasm, but letting it inevitably build to a forgone conclusion.
I looked up at her, across the soft, slight curve of her torso to her face. Her eyes were clenched so tight I could barely see her long lashes. One had was gripping the sheets and the other was at the base of the back of my neck, holding me firm against her sweet, thick lips. She came then. The first of hundreds we would share together. She opened her eyes as her jaw dropped and we looked right at each other as she repeated my name over and over and over through the spasms. It was so fucking hot. I honestly just paused in writing this to have one myself…
I was in heaven. Here was this sophisticated woman that I was proud just to have caught her attention online. Now she’s laid out before me, legs splayed wide, with her toes curling up each time I clamped down on her clit for a buildup to an orgasm. After her second, I let a broad smile stretch across my face, pressed deeply into her lips. She could feel my smile form against her pulsing wetness and she craned her neck up to look down and me. Two succulent, brown nipples framed her face. They became the rest stop on my journey up her torso with my lips. My cock dragged higher and higher against her calf, then thigh, as we came face to face again.
Source: reddit.com/r/gonewildstories/comments/5nvhac/passionate_friendship_with_an_older_woman_mf
do you mind me asking which sites you have found most successful?