by Dudetodude ©
Comments and suggestions are always welcomed.
Please do not copy or distribute this story without my permission.
This is a story involving sex between a middle aged 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.
* * * * *
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 then they get rude or 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.
Being around Cindy was good for me.
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 her age.
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 self esteem biulding
compliments she showered me with, made me feel better about who I was.
I began to swim around. I think I was developing a school girl crush on her.
I’m thinking this is crazy, it’s another woman, I hardly know her, 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 and began to panic.
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, but with each touch
I felt electricity buzz through me and I liked it. 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 I allowed my imagination to soar into thoughts
that were outside of any experiences I’ve ever had. I even thought of swimming
up to her underwater and bumping into her gently 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 favorite 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 at the initial thought and I was horny now.
Maybe that had something to do with the way I admired Cindy 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 and Cindy didn’t seem to notice. 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 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. My skin was wet and slippery from the steam and her skilled hands
felt like silk as they moved effortlessly over my body.
I secretly hoped that 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 needed affection,
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.” She requested quietly and with a casual tone.
I lifted my lazy head slightly and asked her to do it.
I reasoned to her that 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 unclip it.” I said.
Cindy easily unclasped my bikini top strap 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 brushing and lightly touching them. I was in a daze.
When her hands brushed 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, but ever so subtle. Cindy also began to message in close to my
inner 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 but being to obvious about it.
Cindy then undid 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 sly smile and said jokingly,
“You witch! that’s not very nice!.”
I twisted slightly and went re-clip my bikini bottoms but forgot about my
top being undone before sitting up. Startled that my top had not come up off
the bench with my body, 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 back on. “Ok you rat!” I said, “I’ll get you back!.”
Continued: on part 2
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