It Started At The Pool – Part 4

It Started At The Pool – Part 4

I you haven’t read the first three installments, you might want to do so to get the background of what
has transpired with Greg, Cindy, her daughter Jen, and her friend Diane.

Part 4 finds Cindy and Greg are in Bermuda at a boutique hotel just outside of Hamilton. Jen and Diane are
both having roommate problems, and since Diane’s roommate decided to give her notice, the two of them
want to move in together, but are awaiting Cindy’s ok.

Greg is interested in this development, as it might make things easier around the house, and it might also
be safer or less risky to drop over to “visit” the girls on occasion.

Bermuda.

Considering the time of year, Bermuda was still a pretty quiet place, as the tourist season had yet to
begin. Subsequently, Cindy and I had the place to ourselves for the first few days. Then another
younger couple, Tom and Sandy arrived. Cindy and I were hanging around the pool area and patio,
but as the pool wasn’t terribly great for lap swimming, one could still get exercise. Cindy was
lying in the sun on one of the chaises in her bikini, catching some rays. She looked like the image of
her daughter lying there, and still has that capacity to make men (and me) stare despite being north
of 40 years.

We met Tom and Sandy as they came to the pool to relax, and they were clearly a much younger
couple. Each of them was probably about 30 or so, and Sandy, who wore a lovely little (and I mean
little!) bikini that was comprised of little more than maybe 5 square inches of cloth (tops), and a few
strings to hold it all together. I’d guess she was maybe a size 6, and her breasts were easily C-cups.
Her muscles were toned, so it was obvious that she lifted weights or did some other kind of exercise
on a regular basis. Her hair was short and dark brown, and as I learned later, had green eyes.

Tom was a bit shorter than me, but also in reasonable shape. He wore a standard boxer-style
bathing suit, had sandy-brown hair and a medium build.

I took notice of Sandy as soon as she came out of the side entrance to the hotel wearing robe, and
when she shook it off I was taken back by what a great figure she had. She pulled one of the other
chaises over near where Cindy was sunning herself (as she was fully exposed to the sun, the other
chaises were in a shaded area) and reclined back on her chaise.

Tom followed her out, dragged another chaise over next to Sandy’s, dropped off a few things, and
then dove into the pool. We eventually introduced ourselves, and started to chat. Apparently, they
had both decided to take a few days off, and had dropped their only child (a son) at Tom’s parents
house to spend some time alone relaxing. We took note that the women had started chatting, and
Tom asked me how old Cindy was. When I told him she was over 40, he was visibly stunned, and
told me I was a lucky man. I grinned and agreed with him, saying from the looks of it he was also
fortunate.

We chatted about current events, sports, our careers, and other stuff when he piped up with “how
liberal is Cindy?”. No one had asked me that question before, so I asked him “can you define
liberal?”. He smiled, and said he hoped I wouldn’t be offended, but said that his wife Sandy was
also rather fond of women. When they arrived, Sandy looked outside their window down at the pool
after they checked in, saw Cindy sunbathing, and insisted on heading for the pool immediately. I
told him that that was a topic I had never explored with her, as she was my girlfriend, and though
we lived together for some months that topic never came up. As far as I was concerned, it didn’t
bother me, but I couldn’t speak for Cindy.

Tom laughed, said that Sandy would take it slow, would very likely find out, adding that she
usually preferred younger women, but that Cindy just blew her away when she first saw her. I
smirked at that comment, saying that I’d had the same reaction when I met her myself.

It wasn’t long before one of the hotel staff came out and walked over to the ladies, who were chatting
up a storm. Cindy called over, and asked if I’d like a cocktail. I looked at Tom, he said “sure”, and
I said “we’re both up for a drink if you’re ordering”. She waved and the guy from the hotel vanished
inside, eventually returning with some drinks. I hadn’t gotten the full workout, but figured what the
hell, and called out to the women and asked them to bring our drinks over. Cindy and Sandy both
got up and brought our drinks over, and sat with their legs dangling in the pool. When Cindy put
hers down I reached up and pulled her into the pool with me as she shrieked with surprise. Tom
quickly followed suit, and Sandy also got dragged into the water.

Cindy quickly jumped up on my back, so I was giving her a piggy-back ride around the pool. Tom
and Sandy were soon doing the same thing. The horsing around quickly deteriorated into Cindy
and Sandy trying to dislodge each other from my or Tom’s backs, each riding their man as if they
were jousting. They were shrieking and laughing like school girls, when Sandy was successfully
dislodged from Tom’s back by Cindy. When she fell off, her top became unfastened, and mostly
fell off. Cindy then let herself off of me, and swam over to sit in front of Sandy while she put her
top back on. I heard Sandy say “here – get closer – I don’t want him to see me”, and as Cindy
backed herself to her Sandy reached for her shoulders and pulled Cindy in front of her. So close
I was sure, that her breasts were pressed into Cindy’s back.

Tom and I were laughing (me pretending I had no idea of Sandy’s attraction to women), but I was
watching Cindy carefully. Her eyes got really big, and she was clearly surprised, but pretended that
it was all in good fun, as Sandy took longer than I would’ve expected to put her top back on (women
who are in a hurry do that very quickly, I’ve noticed). After she got her top back on, I saw Sandy
whispered something into Cindy’s ear, and then released her. Cindy then swam back over to me,
pulled me close to her, and then suggested we get out to enjoy our drinks.

We got out of the pool, picked up our drinks, put them on a side table, and I went and pulled
one of the comfy easy chairs over, next to Cindy’s chaise. Tom and Sandy also climbed out as
we sat down, clinked our glasses, and took a good pull off our drinks. Cindy had ordered
us mai-tais, which were pretty lethal – whoever poured them was heavy handed on the rum
bottle. We hung around the pool for a while chatting with Tom and Sandy – they were both from
New York and had gotten married in Bermuda at this hotel several years prior. Another few
rounds of drinks went by, and eventually the sun got a bit hot, so I suggested to Cindy that we
head inside for a nap prior to going out for dinner. Cindy excused us, saying that we were heading
for our room for a nap, when Sandy suggested that we have dinner together.

There wasn’t much going on on the Island since it was still too early for tourist season to begin, so
Cindy took down their room number and said we’d get back to them a little later, and otherwise we’d
see them tomorrow. They said that was fine and back to our room we went.

As soon as we got into our room, Cindy let her robe drop, took off her bikini, and announced that
it was time to wash the chlorine off. So I dropped my swimsuit and towel and we stepped into the
oversized shower in the bathroom. We soaped each other over and kissed deeply in the shower,
enjoying the feeling of the slipperiness of the lather as we held our bodies together. I became
aroused while I was soaping down Cindy’s back, and I pressed my cock into ass as I caressed her
breasts. She moaned happily and quietly suggested we get out of the shower. We rinsed off and
dried each other carefully. Cindy took out the hairdryer, and turned it on while I moved into the
bedroom and lay out on the bed.

She finished her hair quickly (her shorter hair made that a much faster chore), opened the door,
and sensuously walked over to the bed where I was laying. I watched her as she came to me,
smiling. I moved over to make room for her. She climbed onto the bed and lay on her side next
to me, pulling me close, and kissing me deeply. She turned over and asked me to hold her, which
I did happily, running my hands up and down her body, as she sighed.

I asker her if anything was wrong, and she said “I’m not sure”. “How so?” I asked. “Remember when
we were in the pool, I knocked Sandy off Tom, and her top fell off?” she asked. “Sure do” I said,
“that was hilarious”. “Well, remember that I went in front of Sandy to hide her breasts from you while
she put her top back on?” she asked. “Yes – I saw her pull you back” I said.

“She sure did, in fact she pulled me so far back that I could feel her pressing breasts in my back” she
said. “Oh. And?” I sad. “She said she hoped it wasn’t too forward, and didn’t want to offend me, but
that she really found me very attractive” said Cindy. “Really. And how did you feel about that?” I
asked her. “I’m really not sure” she said, “she is a lovely woman, so in a sense I suppose I should be
flattered. But I love you” she said. “And I love you” I said. “Is there anything else that happened
there that I should be aware of?” I asked, and I slid my hand down and pulled her over so she was
lying on her back. I then ran my fingers between her legs, and noted that Cindy was really wet.
“Hmmm…” I whispered into her ear. “Hmmm what?” she asked.

“You’ll have to pardon my observation, but you’re awfully wet. Are you sure you’re not really sure?”
I asked softly. “I’ve never been with a woman and never even considered it” she said, “and I just
don’t know about that. Still, she is a lovely woman and I found it flattering”, said Cindy. “And
arousing” I said. I started to kiss her shoulders, and slowly up her neck. Then I moved over her and
gave her a deep kiss, as she put her arms around me and clung to me. I ran my tongue down her
neck to her breasts, took each one into my mouth, working her nipples until they stood up, and kissed
her down to her abdomen while I ran my hands over her body. I soon moved between her legs, and
kissed the insides of her thighs, eventually centering on her pussy. She was soaking wet, her inner
lips already parted, open, and inviting. I reached to her with my tongue and licked her from the bottom
to the top of her slit, finishing at the top of my initial assault on her pussy by sucking her clit gently into
my mouth as her hips thrust up to meet me. Her back arched in pleasure, and she moaned lustfully.
I stayed centered on her clitoris and kept sucking it into my mouth, drinking her juices as her hips
gyrated slowly and her fingers ran through my hair.

I moved down a bit and then dug my tongue into her opening, pushing it in and out to fuck her. Now
her hips were moving with me as much as she could, when I moved back up to her clit, found her magic
button, and circled it with my tongue. Her body instantly tensed, she pulled me into her pussy as
I sucked her clitoris and she rewarded me with a rush of wetness, grinding her pussy into me while I
sucked her. I rejoiced as I looked up at her tight body, frozen, with her abs beautifully defined, her
eyes clamped shut, and mouth open, as she held me in place. When I moved my tongue she pushed me
away and covered herself, gasping out “too sensitive, too sensitive”. I looked down, and there was a
considerable wet spot on the linens.

I pulled myself up over her, and my now rock-hard cock found her opening. I slid into her in one
motion, and lowered myself to her giving her a deep kiss as she tried to drink all the fluids out of my
mouth. “See how good you taste?” I whispered, as I started to move in and out of her. Her body
began to respond immediately, and soon I was up with my arms fully extended, watching her push
herself up to meet my thrusts, her breasts heaving, eyes shut, and smiling. I was really turned on
watching her, and I felt my orgasm building. Her body began to tense as her inner pussy muscles
started really working over my shaft. I looked down to see my cock sliding in and out of her, felt
my balls slapping against her pussy, when it all became too much and I felt my cock almost vibrate
as several ropes of sperm injected into her womb, the impact of which made her come. I watched
her body thrash as her inner muscles almost squeezed me out of her. I pushed back, feeling her
pussy grasping my cock. Eventually I collapsed on top of her, leaving my still hard cock inside.

“Ya know” I said, “I don’t blame Sandy for propositioning you.”

Cindy smiled and said “oh yeah? Why?”. “Because I find you deeply attractive mentally and physically,
and I love sharing a bed with you, thats why” I said. “You were right”, she said, “her propositioning me
did kind of arouse me”.