Loading...It was a blow to my ego to find myself dealing with an online dating service. Lonely Hearts club is what it was. No matter how nice they dressed it up. No one wants to find a partner that way. Hell, there was a time when I could just snap my fingers and…
OK, there never was such a time. I always had a hard time talking to women.
And an even more difficult time getting them into bed. Women seemed to like me but only “As a friend.” Or even worse: As a brother!. So, eventually, after the end of my marriage and a lot of lonely nights, I signed up at this online dating service.
“No commitment!” It promised. “Just a coffee date to start out with!” It continued. “Move along at your own pace!” It concluded. Pushing fifty, I was actually more interested in finding a woman I could get along with. For sure I wanted sex and wouldn’t be interested in a relationship that didn’t include plenty of that but, on a continuous ongoing basis, I was looking for a drama free lady. Someone I could kind of be friends with.
Easier said than done, I know. Anyway, I listed my “Interests,” being careful to avoid stuff like “Long walks on the Beach” and “Weekends in Santa Barbara” and sent the thing in. I hate being photographed and declined to include a picture. I’m not, you know, really ugly or anything but I just look so much like my Dad these days that it makes me uncomfortable.
Sure as you’re born I got a couple of hits the first day. One looked kind of interesting too. Rachel was her name. She said she loved music and went to concerts at least once a month. She had been married but had no children and claimed she just wanted a comfortable physical relationship, adding she “Wasn’t a gold digger.” Good thing. I own a small business but Lord knows, I’m not rich.
We contacted each other online and exchanged the obligatory emails. All friendly. I might have goofed up when I mentioned that I was a fan of the Grateful Dead. There’s a certain amount of…embarrassment, for lack of a better word, about admitting you’re a dead head. People assume you spend every possible moment out gyrating in the sun, taking dope and boogying like there’s no tomorrow. I like all kinds of music but when I saw the Dead as a young lad, I was blown away by the level of their musicianship. The ensemble passages they routinely played and played so well. It was like, all the other bands back then were trying to get to a certain musical place…and the Dead were already there!
Anyway, Rachel emailed back enthusiastically about her love for the band and asked me if I wanted to attend their upcoming show at the L.A. Sports Arena. I was not sure I wanted to spend an entire “Blind Date” at a Dead show so I countered with, “How ’bout a coffee date…like it said on the website?”
So we met after work on a Thursday evening. Rachel agreed to wear a rose in her hair so I would recognize her at the Pantry which is Downtown. Crazy restaurant. “There’s always a line! The food must be good!” is what “They Say.” Actually it’s a dicey neighborhood so you have to get buzzed into the place and they don’t let you in unless they’re good and ready so, yeah. There’s usually a line.
Rachel was a good sport about going there and so I was outside, waiting when, at last she walked up. Sporting the Rose in her hair and a vintage Grateful Dead tee shirt. I was…underwhelmed.
“She’s too young for me.” Was my first thought. I know, I know. It sounds crazy cause, the younger the better right? But I was really looking for something more my age this time out. Rachel couldn’t have been more than 35. And physically, from what I could see, she was OK. Blue Levis, tennis shoes, the Dead shirt, long black hair. But her face! Maybe it’s the pot calling the kettle black here but she had the deep set eyes, set close together, kinda big nose, thin lips…just not my type at all. I couldn’t just bag the whole evening so we went in the Pantry and ordered dinner. I know I said just coffee but, hell, it was dinnertime.
We waited for our food and, it was awkward to say the least. I was finding it hard to make conversation so Rachel carried the ball the bulk of the time. I kept thinking “I can’t picture myself with this woman. She isn’t horrible and she seems to have a nice body but…but she’s just somebody else’s girl, not mine.”
Midway through the meal, which I was gobbling down hoping to end it as soon as possible, Rachel mentioned that she lived in a loft just a few blocks away. We chatted about what it was like living downtown and she said basically it was fine unless the Lakers won the title in which case it was bedlam! “I love the Lakers.” I blurted out.
“So do I!” She fired back. And on the went about team. How much she admired Kareem. Loved Chick Hearn. She’d actually met Jerry West once upon a time and Pat Riley was her ultimate heartthrob!
Now we were clicking and the conversation started to flow. My dinner was getting cold but I didn’t care. She mentioned Kareem’s love of jazz and it turned out both of us were deep into Miles Davis and John Coltrane.
It was right about then that I noticed her little smile. She shot it once in a while and it was very subtle. Just the corners of her mouth would turn up and this twinkle appeared in her eyes. She would hesitate before speaking as if she had thought of something funny. Rachel was actually kind of pretty if you knew what to look for.
So Rachel invited me to see her loft over on Sixth street and I was ready to go. We walked to my truck and I opened the door for her like a gentleman. As I did so, I noticed that her ass was doing a pretty good job of filling out those Levis!
It was dark now and Rachel’s black hair was shining in the street light. We entered her Loft and it was beautifully furnished. I would call it modern Chinese style with lots of black and red. Wonderful Chinese prints on the walls, and sparse but comfortable furnishing. Rachel went over to the Hi fi unit and put on a vinyl LP of Miles’ Kind of Blue.
I made my way to the kitchen and quickly cooked up a couple of Martinis while Rachel went to the bedroom to “Change into something more comfortable.”
Now I was really interested! Her home was not adorned with dozens of Grateful Dead posters, She appeared to have a job and she loved the Lakers. I found myself thinking how quickly I’d made a decision about this woman based solely on her face. What a stupid thing to do.
Rachel emerged from the bedroom wearing a black dress. And it looked good on her too. Low cut in front, I could appreciate her womanly breasts with this outfit. And they were pretty big! I’m not a tit man per se and I was thinking about what I checked on the Personal Information page of the dating service. I generally like small busted women but I couldn’t remember what I wrote. The only thing I did remember was, it asked if I had any sexual “Kinks” and I wrote “Panties.”
Rachel sat down next to me and we sipped our cocktails as “So What” filled the room. I’ve heard that song a million times but somehow, it sounded different that night. My ex-wife had no use for Jazz insisting it “Made no sense.” Rachel obviously understood what the musicians were going for when they recorded that tune.
We listened silently to Adderly’s solo and then, at the end, Paul Chambers wonderful bass line which is so perfect. I was looking into Rachel’s eyes during Blue in Green and then we were kissing. Her lips were soft and welcoming. I didn’t rush things and we smooched and cuddled for a few minutes as the album played.
Rachel got up to turn the record over and when she bent down to do so, her panties were briefly exposed. Oh, just for a nanosecond but I saw her little white panties. She started side two and padded softly back to the sofa. She snuggled up to me and whispered “Did you like what you just saw?”
I felt just drunk enough to answer: “I liked it a lot Rachel.” We looked into each others eyes for a moment and I was suddenly at a loss for words.
Not to worry. Rachel seemed to know what to say. “I put these panties on just for you Matt.” She gave me that little smile when she said it. I assumed she had read about my little “Kink” and so I didn’t need to apologize or anything. She knew what I liked even beyond Jazz and the Lakers.
“Would you like to…touch my panties Matty?” She whispered.
I didn’t need to be asked twice. My cock jumped when I heard what she’d said and I never spoke but just moved my hand down to her legs. More kissing ensued and I slowly slid my hand up Rachel’s leg until I was way at the top of her thighs. I hesitated for just a moment and then grazed my fingers up further until I was touching Rachel’s white panties!
“Mmmmm…that’s nice Matt.” She cooed softly in my ear. “Slip your fingers inside the legband.” I did as she had requested and then I was touching the smooth pink flesh of Rachel’s pussy! I felt her move her legs slightly further apart so I could get a little better feel of her tightly closed lips.
“Don’t take off my panties Matty!” She told me. I wasn’t really close to doing anything like that but I loved it every time she said the word “panties!” I wanted to hear it again and again!
“Let me pull down your panties Rachel.” I begged. “You know you want me to touch you down there…on your bare pussy!”
“Noooo!” She teased. “You can’t just strip me naked like I’m your little whore!” Rachel was again giving me that little smile. “I’m a good girl! You can’t take off my panties and see my pussy all naked!”
I kissed Rachel deeply and stuck my tongue way into her soft warm mouth. She moaned in appreciation as she felt my amorous attack, kissing me back for all she was worth. “I’ll…I’ll let you look at my panties Matt…but that’s all!”
With that said, Rachel lifted the hem of her slinky black dress and slowly pulled it up until, at last, she exposed her tight little white panties to my excited eyes! Just simple white cotton bikini panties but my God, the sight of them was causing me to harden like crazy! And the heavy lidded look in her eyes seemed to promise more! I glanced down and you could just barely make out her black pubic hair through the thin fabric of her panties.
“I know you’re a good girl Rachel.” I told her with at least some sincerity. “And I don’t need to take off your panties tonight.” I watched for her expression as I added, “How about some Chet Baker? Got anything by him?”
Rachel caught my drift and went over to the record rack where she looked for a moment and then pulled “My funny valentine” out and then knelt down to put the record on. She looked back at me mischievously and then reached back and lifted her dress to expose her panty clad ass! The shapely black haired girl took her time setting the needle and wiggled her butt a couple of times before returning to the sofa where I waited.
“You’re lookin’ good honey!” I told her. I kissed her again and reached around to unzip her pretty black dress. Rachel offered only token resistance before allowing me to tug down the zipper and free her breasts. They were magnificent! I gave an involuntary gasp when I finally saw Rachel’s tits and she smiled at my reaction.
Thinking about it later I realized that Rachel is one of those women who just plain look a lot better out of their clothes than they do dressed. Her big ripe tits were capped by delicate pink nipples. No sag whatsoever when she moved. Just a bit of jiggle which I found to be wildly exciting.They were a handful that’s for sure. I managed to slip the black dress off of her body which left my date dressed only in her little white cotton panties.
I pulled Rachel to me and gently slid my hand down to fondle her pussy through her panties as she moaned horsely into my ear. “Oh Matty, Don’t take off my panties! You can…you can suck on my nipples but please don’t pull down my little panties!”
Again she kept saying that word “Panties.” And she was getting to me…big time! I needed no further encouragement and went after those big firm titties right away, locking my lips on her nipple and immediately feeling it harden in my mouth.
“Oh that’s it Matty!” she gasped. “Suck my nipples while you feel up my…my pussy!
I took that as an invitation and stole my hand beneath the waistband of Rachel’s panties. She had shaved the lips bare but left a patch of pubic hair just above. I had to see her pussy! I just had to!
“Let me see your pussy Rachel!” I pleaded. “I won’t take your panties off but please honey! Please let me see it!” I ran my forefinger right over her now very wet pussy lips and then pushed into her desire swollen hole. Rachel buried her face in my shoulder as she allowed this intimate contact and then whispered in my ear.
“You stay here, OK? I’ll…I’ll let you see.”
With Chet now singing “Let’s get lost,” Rachel moved to a small mahogany chair with red tufted upholstery that sat across the room. She sat on the chair and eyed me to be sure I was paying attention…like I was going to look away now! She then reached down and slowly pulled the legband to one side and completely exposed her tight little pussy to me!
My black haired blind date looked down at her pussy and then up at me. She moved her finger down and lightly teased herself as I watched. I felt the time had come and stood to remove my pants. Rachel watched me as I did so and, when my now furiously erect penis came into view she seemed pleased. I remembered her comment on the Information page of the website about wanting a “Physical relationship.” Well, she was about to get it from me.
I stroked my cock a bit as Rachel watched and then she climbed off the chair. She turned around and then knelt on the seat, putting her world class rear end on display. Knowing she had me now, Rachel reached back and began to roll her panties down to show me all of her ass. Wow! Easily the best ass I’ve ever seen! Not fat mind you, just all plump and ripe and ready to be spanked!
I had all kinds of lewd thoughts going through my mind right about then but Rachel took the bull by the horns. “Come over here Matt.” She quietly said.
I was there in an instant and began to run my hands over her butt enjoying the silky smooth feel of her flesh. I slid my fingers over her little dime sized asshole on my way to her now glistening pussy lips. She was good and horny too now and I took hold of the waistband of her panties and began to pull them down.
“No! Please, No Matt! Don’t take off my panties! You can have me any way you want but don’t strip me all naked!” She pleaded.
I was now over the top excited by all of Rachel’s teasing and unable to wait much longer for release. I knew she wanted to be fucked so I took hold of her hand and dragged it to my cock. She eagerly grasped it and moaned when she felt just how thick and hard it was.
“Put it where ever you want it Rachel.” I told her. Then I waited to see what she would do.
Chet Baker was singing “Like someone in Love” when Rachel drew my prick right into the valley of her splendid rear cheeks. She touched it momentarily to the slippery lips of her pussy before lifting it up to the tightly closed hole of her anus. My eyes widened in surprise but I gave her no chance to back out. I began to apply pressure to Rachel’s little asshole until I felt it begin to cave in. And then…gloriously I surged into her ass!
“Oh Matty!” Rachel gasped in protest, “Don’t fuck my asshole! Oh please no!”
“Well then take off your panties and I’ll stick it in your pussy honey.” I shot back, all the while forcing more and more of my hardon into her incredibly tight asshole.
“Not…not my panties!” She wailed. “Oh…Oh go ahead then! fuck my little asshole! fuck it good Matty! Shove it all the way in there!”
I did just that. Pushing harder and harder I finally managed to root myself right to the balls in Rachel’s teasing little asshole and I gasped in pleasure when I realized how completely I now had her. “Rub…your…pussy…with…your …panties Rachel.” I told her as I fucked into her ass over and over.
“Not…not in front of you Matt!” She complained. “Don’t make me…masturbate right in front of you!”
I continued to bury every inch of my cock in Rachel’s poor little asshole as I felt her fingers now working just below, teasing her panties into her pussy flesh. “Oh Matty, It’s…It’s so nasty!”
And that it was. We’d only met a few hours ago and here we were in her loft, Rachel virtually naked except for her useless little panties, my cock plundering her defenseless little asshole while she did her best to pleasure herself with her fingers.
I knew I was going to come and very soon now. I reached around to Rachel’s nipples and got a good feel of them as I continued to sodomize her. “You’ve got a hot little asshole Rachel,” I confessed. “You’re something babe!”
“Damn right I am Matty!” Rachel smiled. It was as if she was waiting to hear that. “Now go ahead and fuck my asshole hard and deep and, when you’re ready to come, come all over my nasty little panties!”
There it was again…that word that seemed to short circuit all of my senses. “Her panties!” I thought to myself “She wants hot come in her panties! Well OK baby, here it comes!” I poured everything I had into a dozen or more ball jarring strokes and then jerked my erupting penis from the depths of Rachel’s forever stretched asshole and began to spurt sticky jizz right into her panties!
“Oooo Matty!” Rachel called to me, “That’s it…come on my panties! Give me all you’ve got now! Wet my panties with your creamy hot sperm!”
It was one of those orgasms that, for the next half hour or so, my cock would occasionally twitch from the intensity of the experience. I held Rachel until Chet was through and then we listened to “Sketches of Spain” and had a glass of wine. We talked until dawn.
I don’t know if it would be accurate to say that I “Love” Rachel. I’m also pretty sure she doesn’t feel that way about me either. Maybe love like that is for younger people. But we seem to scratch each other’s itches. We have a great time together on our “Dates” and I don’t bother looking for anyone else on that website. I guess you can be lucky in this life.