Relaxing Ride Ch 1

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Please do not copy or distribute this story.

This is a story involving sex between a middle aged woman and a 21 year old woman. This is a subject near and dear to me. If anyone has any lesbian stories involving age differences, I would appreciate reading them.

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I was invited to spend a few days at my older brother's condo in Florida with his wife and my niece and nephew.

Since I was between jobs, I thought it would be a good idea to take the drive down from Michigan to Fort Lauderdale. What the heck, I've never seen that part of the country and the long drive would give me a chance to figure out my life. You see I'm 21 years old, dropped out of college after a year to work, and now I'm between jobs, between boyfriends and I'm still living at my parent's house. I've only had 2 boyfriends and those relationships weren't serious ones. I haven't had very much sexual experience, and I guess, I'm comparatively naive in many things. I always considered myself a little shy and a little on the ugly side compared to some of my girlfriends. Although I have a reasonably nice figure, 34-26-36, at 5'4", I always thought my butt was a little chunky and I'm self-conscious of it. In reality I'm really not built too bad for a 21-year-old. My biggest enemy is my own lack of self-esteem.

Well I packed up my little Sunfire car and headed out early on this beautiful spring day hoping to get in a full day's ride. The trip began virtually uneventful and boring. I even nodded off to sleep from time to time while driving. Thats when I thought I should find a rest area. The most exciting part of the trip so far, was another woman driving by herself and I would pass her and she would pass me. This helped to break up the monotony of the drive. I later pulled off at a rest area to have a pee and take a needed break. I noticed the woman in the other car pulled into to the rest area as well. I did my bathroom thing and then sat out on the park bench to enjoy the sounds of the birds and have a cigarette. I didn't see her go into the bathroom but I noticed her when she came out.

She came over and sat on the bench beside me and lit up a cigarette. We made small talk about the birds and the weather and the long drive. She lived in Ohio and it so happened that she was on her way to Florida as well, Jacksonville I think she said and she was regretting that she didn't fly instead since she's a little uneasy about the long drive. I told her I felt the same way but was looking forward to seeing some sights along the way. To describe her, I figured her to be around 45yrs old, maybe a little older.

Heck you can't tell the age of people these days, at least I can't. I know that she was much older than me. At 21, everyone looks older. At any rate, she certainly looked good for an older woman. She was slim, around 5'6", slightly taller than me. She was wearing tight fitting CK jeans, a pair of Nike runners, and a plain white T-shirt neatly tucked in that emphasized waist line and her breasts protruded out just slightly under her slightly loose fitting T-shirt.

She wore a dark blue silk jacket and she had it undone. I'm thinking, for an older woman she sure has perky looking breasts and wondered if they were real or just her bra doing an exceptional job. She was slightly slimmer in the ass than I was which just further confirmed to me that my butt was too big. I could see from her jewelry make-up that she was well to do. I admired her appearance and could see that she looked after herself, with her nails just perfect, her hair nicely set, and cut just above her shoulders. This lady was classy. Most of all in that very short period of time that we spoke, I was impressed by her bubbly and positive attitude. I like being around positive people, maybe because I'm so unsure of myself I tend to feed off the positive atmosphere.

When she spoke, to me, she symbolized the portrait of an ideal, classy and graceful woman. The type of adults I admire most. Her make-up looked like it was done professionally and I noticed that she wasn't wearing a wedding ring. Not that it was important but it's just something I noticed. In all, she was a very classy and attractive woman and I was sure that even at her age she was still causing a few men's heads to turn.

We finished our cigarettes and she introduced herself as Cindy. I told her that my name was Rose, I said "its short for Roseanne". She suggested that since we're going in the same direction, we could stick together on the road and that way watch out for each other in case of car trouble or whatever. I thought that was a wonderful idea and I would feel more secure especially since I've recently has some car trouble. She thought it to be a good idea as well. We hit the road, and after about 3 hours more of driving, she signaled that she was going to pull off at the next exit.

We fueled up and pulled into the restaurant next door for a bite to eat. We ordered diner and a glass of wine. "At least it wasn't a dry county," she said. I agreed and I felt pretty cool now that I was drinking legally. Not that I could never get a false I.D. before but now I didn't need it. As we ate our diner we talked about everything and anything. She asked me all sorts of questions. What I liked, what bands I like, my dislikes, my ambitions, my goals and my life. Cindy appeared to be genuinely interested in knowing about me and I liked that since I didn't really have any close "best girlfriend" to talk to. No one has ever taken the time to get to know me. I guess that goes both ways though.

This woman made me feel pretty good about myself. Looking back, I suppose I was a very naive and impressionable 21 year old. I asked her a few questions about herself and Cindy told me that she has been a widow for the last 5 years, her two grown boys just moved to Florida and now at 48, she's finding it lonely by herself. She has a few friends but with all the moving around her husband did for work while he was alive, she was never able to firm down a close and true friend. She explained that although at first impression, most people view her as being very confident and professional, Cindy confessed that she actually felt rather insecure about herself. It wasn't until after her husband died that she became a stronger person. She said that time and experience can be great teachers. That blew me away! I could relate to her so well. It was like she understood exactly how I felt about things. Well after listening to her experiences, I knew there's so much more in my life to experience. After hearing about her experiences I actually wasn't feeling so depressed and could see my own personal problems much so smaller now than they were this morning.

We paid the bill and she asked me if I was planning to stop for the night or try driving right through. I said "actually I hadn't made up my mind but that I guess I really should find a room for the night,"

"and try getting an early start in the morning." She said that that was her plan. Neither of us felt like driving at night anyway. I told her I was on a tight budget so I had to find something inexpensive. She chuckled, "Yes I know how that is" she said. It was already 6:00pm, we agreed we might as well try for a room right across the street at the Hampton Inn.

When we checked at the front desk, only room available was a no smoking room with one king-size bed. The clerk didn't think there were any rooms available in the immediate area since there was some spring flower festival of some sort going on. This presented a decision for me. I considered quickly to let her have the room and I would just keep on driving. We looked at each other, she noticed my concerned look and waited for me to decide. "Go ahead and take the room," I said "I'll just keep driving I guess" I really didn't feel like driving anymore tonight I thought. Then she said, "don't be silly," we can share the room if you don't mind, my treat"

"That's very kind of you but really you don't have to inconvenience yourself for me."

"nonsense," she said it's no bother at all," and with that, she turned to the desk clerk and said "we'll take it." Turning back to me with her now familiar smile she said "besides it's either this or that dreadful drive." As for me, I didn't mind at all, since my finances were low and I didn't want to stay in some rest area part of the night, this would be perfect. Besides, I thought it would be fun, she's a really nice lady. I liked my newly found friend. She was pretty cool, more like a big sister or close friend than just another adult.

We got up to our room on the second floor and I was feeling a little excitement since I've only been in a hotel on two other occasions with my parents when I was very young. I was thinking to myself how grown up and sophisticated I was feeling right about now and how considerate Cindy has been. I thought it pretty cool that in such a short time, Cindy and I had become friends. I especially liked how comfortable I was talking to her. Like I said, she made me feel good about myself, like I was on her level. Putting it all together in my mind as I climbed the stairs to our room with this older woman in front of me, almost a stranger yet a friend, I felt a wave of excitement come over me.

Anyway, we got to the room and I had never seen a king size bed before. It was huge! I said " I could get lost in that thing" Cindy laughed at the expression on my face and said "then we'd have to send a search party out for you." We unpacked a few things, put out our make-up bags, and hung up some clothes for tomorrow. I couldn't help admiring some of her clothes as she systematically hung them in the closet. She folded her fine lingerie neatly as she placed them in the drawer. Then she plopped down on the bed letting out a gasp of relief and I sat on the sofa feeling relaxed.

"So do you want to watch TV?" I asked figuring it was too early for bed. She suggested we try out the pool. After a long drive and a refreshing swim, we'd sleep like babies. "Great idea" I said as I dug for my new bathing suit and moved toward the bathroom. I had just bought a new two-piece for this trip and was dying to try it on. It was black and I thought, apart from my chunky butt, I looked great in it. I looked at myself in the mirror in the bathroom as I adjusted the straps thinking not bad. I felt a little self conscious though now realizing that I would be barely dressed in the presents of an almost perfect stranger but then again I reasoned, we're both woman and she would be changing into her suit as well so what's the big deal. When I came out of the bathroom, Cindy's face lit up and she commented how lovely I looked in that bikini and that black was defiantly my color.

My face turned red with embarrassment but I did enjoy the compliment, especially coming from her. I said thanks and told her I had just bought it. I showed her the cool little adjustable snap clips on the sides of the bikini bottoms, she said "how neat! easy on, easy off model eh?" we giggled. Cindy had already changed into her suit and had been doing some final adjustments in front of the mirror just as I came out of the bathroom. I caught a quick glimpse of her as she adjusted herself and I must admit, I enjoyed the peak. I thought she looked sexy! I said "geez I hope I look as good as you do when I'm 48. She smiled and said thanks but that I looked great and would defiantly look better than her at 48 any day! Cindy had complimented so many times today I lost co I felt myself get flush again and I hopped she didn't notice. With both of us changed into our suits, we donned our wraps, and towels, and headed for the pool.

It was an indoor pool and surprisingly to us, it was deserted. We were the only ones in there. With the hotel being at full capacity, Cindy had expected it to be crowded. Cindy commented "great! I hate it when the pools are crowded I feel so self-conscious," I'm thinking to myself, ya right! "It's usually occupied with screaming kids or old fat businessmen that constantly undress you with their eyes." She says. "Some of those old guys can be such pigs, it really turns me off."

"Yea" I said, "I get that sometimes and I hate it to. I don't mind the younger hunks checking me out but some of those old farts at the mall or wherever can be such perverts." She gave me that knowing nod.

Tonight, being around Cindy, I was really feeling grown up and mature. She had a way about her that made me feel safe and comfortable. I knew I could talk to her about almost anything. Since losing my job and my boyfriend, I've felt inadequate and immature but today, well not today.

Cindy took off her wrap and laid it on a chair with her towel. She walked to the poolside with a little wiggle in her steps almost as if she was purposely exaggerating her sway. Cindy stepped down into the water. She was really quite slender with hardly an ounce of noticeable fat on her. Her figure still exhibited those envious curves and yes, I envied her. For some reason the thought of Boticcelli's Venus, the sculpture that I selected to write about in one of my art classes came to mind. I didn't realize then but I was staring at her.

"I bet you get a lot of young hunks and old farts checking you out Rose" she said as she stepped into the water and turned to face me. I was a little embarrassed thinking she noticed me staring. For a moment I had been mesmerized at the site of this classy lady in her two-piece. I was noticing again just how attractive and how confident of a woman Cindy was. I was admiring her and thinking how I would like to be more like her. Her yellow two-piece contrasted against her tanned figure and I wondered if I would be able to wear a bikini like that when I was her age. Like I said, although she was much older than me, her figure didn't look it.

She looked up at me and said "come on in, the water's warm." By now I had removed my wrap and to my embarrassment, my nipples were hard from the cool air. I think she noticed that! I tried to jump in as quickly as I could. I knew the air was a little cool but it was more than just cool air that hardened my nipples. I never considered myself to be very attractive but being around Cindy, with her positive attitude and the compliments she gave me had made me feel better about who I was. I began to swim around. I was beginning to have a crush on her. I'm thinking this is crazy, it's another woman for God's sakes she's old enough to be my Mother. Maybe it's because she's so mature or maybe I'm mistaking admiration for lust. Whatever, I was getting that familiar tingling feeling down there.

We swam around a little. Cindy was trying out some swim strokes. We had a one-lap race, and I think she let me win. We splashed around and from time to time, we wrestled in the water to try and make the other fall. We were carrying on just like a couple of kids! Cindy would swim under water to see how long she could hold her breath before coming up for air and sometimes, while swimming underwater, she would bump into me or touch me by mistake with her arm or leg. Once she even bumped her head into my butt underwater. When that happened, she popped up and said "sorry! I had my eyes closed." I thought nothing of it. I was having fun. It had been sometime since I've had a smile on my face and I was actually enjoying myself.

I was swimming underwater as well to try and beat her record for holding our breath. I found myself using that opportunity to sneak a peak at Cindy. I especially enjoyed watching her doing the crawl as her legs opened and closed underwater and causing my imagination to soar. I even thought of swimming up to her underwater like she did to me but I chickened out. Really I thought to myself, Cindy was a pretty hot looking woman. Now for me, it had been awhile since I had any sex at all other than with my toys which I kept well hidden in my room so my mom wouldn't find them. Heck! I've been so desperate lately that once I even considered trying to get the dog to fuck me but that thought left me just as fast as it came up. Needless to say, I was horny.

Maybe that had something to do with it but I knew then that I was attracted to this woman and I didn't know what to do about it. I quickly dismissed the thought and came up for air. To get away, I complained about the kinks in my neck from driving and with that I jumped out of the pool into the bubbling hot tub. She said "great idea" I'm right behind you. We floated and relaxed together in the hot tub in silence. I could feel her feet touching my legs in the water as we allowed our bodies to just float and relax. Unintentionally my feet and legs would casually float and touch her. I was becoming light headed, I suspect from the hot tub and the change in temperature from the pool so I decided to head for the sauna as a final stop before taking a shower.

I lay flat out on my tummy with my arms folded underneath my head on the top bench in the sauna. Alone, now I could collect my feelings about what's happening. The heat from the sauna felt good. In my mind I'm thinking I'm letting my imagination run wild. This woman has no interest in me that way. Hell what am I saying, I've never even looked at a woman that way before. This is crazy!

Just as I was about to doze off, Cindy came in. She scooted up to the bench below mine and began to message my shoulders. She startled me at first then whispered in her bubbly manner, "this should loosen those kinks, a hot sauna and good message does it for me every time." After the long day of driving, the message felt good. I was feeling so relaxed, I let out an involuntary moan and I after, hoped she didn't hear it.

Cindy continued to message my shoulders and neck. She would move her hands down my back, across my shoulder blades, and from time to time her hands would move to the sides of my ribs and lower back, then back up to my shoulders. I couldn't help it I was getting very horny. Crazy thoughts raced through my mind of getting a full body message in the nude by this woman. I secretly hoped that for a moment this is what she had in mind. My hormones were getting the better of me. I decided right there and then that if anything was going to happen, I was going to go along with it. I wanted something to happen, I wanted it to go somewhere, I wanted Cindy!

I felt so relaxed as she rubbed her hands up and down my sweaty back. Then she caught her finger on my bikini strap and broke a nail. "Shit!' she says "I broke my nail. Unclip your top so I don't break any more, it's getting in the way." I asked her to do it. I reasoned that I can't be responsible for any more broken nails but I'm too comfortable to move. "If you can't work around it then take it off." I said. She easily unclasped it and I was feeling calm and free with out my restricting top cutting into me. Cindy continued to massage my back and her hands would move much closer this time to the sides of my tits actually touching them. I was in a daze. When her hands came close to the side of my globes again, I would instinctively raise myself slightly so that she could get to them better and she did, ever so slightly. Cindy also began to message my thighs. Her hands would move along the inside of my legs, around the outside and up again to my back. Each time she would message my inner thighs, I would again ease myself up just a little and spread my legs just a little more hoping she would go further.

Cindy managed to undo the clasps at the sides of my bottoms and started to laugh. She said "ok you can get up now" Still in a lazy daze, I looked at her with a smile and said "you witch! that's not very nice!." I re clipped my bikini bottoms but forgot about my top being undone before sitting up. Startled I covered my breasts with my crossed arms and we both started to laugh. Cindy was on the bench rolling over with laughter at the look on my face. I quickly put my top on. "Ok you rat!" I said, "your turn."