Wife Watching Vacation

This was a story that I never thought would have
happened in a million years. My wife, Cindy, and I had
been married for five years and took an anniversary
vacation to Jamaica. We had been planning it for 6
months and were both extremely excited about being able
to get away from the day-to-day tasks. My wife is a
wonderful mother of our 3 year-old daughter. She is
very beautiful both in her looks as well as her out
going personality. Many of my friends have commented
openly that they are jealous that I have a wife with
such attractive features and fun loving approach to

She is 5 feet 4 inches tall with beautiful blond hair
and blue eyes. Nice size breasts, not to large but
perfect for her body. She is very conservative though
and would never wear anything that was overly daring.
She rarely wears a skirt, and when she does, they are
always about knee length. She would never go out in
public without a bra and has only done so a few times
around the house.

For this trip I told her that I would handle most of
the details of packing, reservations, etc., so she
would not have to worry about it. She gladly accepted
the offer. She picked out the clothes she wanted and
left them on the bed for me to pack while she was
putting our daughter to sleep and finishing other last
minute details. I did the rest of the packing, gathered
the plane tickets, etc.

As a surprise, I had bought all new under garments for
her from Victoria’s Secrets for the trip. No G-strings
or any thing like that, but all lacy things and many of
them somewhat or very transparent. Clothes that she
would normally never buy for herself but that I felt
she would enjoy. I also bought her two new swimsuits.
One was kind of a standard bikini but very cute. Made
more of a silk material where she usually buys one-
piece cotton swimsuits.

I bought a second bikini that was a three triangle silk
material bikini. It had ties at the hips and a tie at
the neck. I debated a long time on getting it because I
did not want her to end up wearing one suit all week,
or shopping for another one while we where there. I
finally said what the heck and got it.

I laid out the clothes for her that morning and she
noticed the new clothes commenting on how lacy they
were, gave me a quick kiss, and thanked me for the
thoughtfulness of getting the vacation started. We took
our daughter to her grandmothers for the week and
headed to the airport. The flight was great and we
really seemed to relax immediately. The place where we
were staying was a series of individual units with a
main area that housed the restaurant, pool, etc. They
had been recommended by friends of ours and really
offered much needed peace and quiet.

We walked the beach and just looked around the first
day enjoying the area. It was all that we had hoped.
My wife headed up to get a shower and I got more
information from the lobby. I noticed an offer to get
massages and inquired. I found the cost very
reasonable. They offered single sessions or packages
for multiple days. I went ahead and bought a package
that would get Cindy a one hour massage every day we
where there at 2:00 in the afternoon. They would bring
the table to the room and everything at 1:45 to set it
up. They recommended the afternoon session because the
beach gets very hot for the average traveler that is
not used to the sun. When I got back to the room, both
of us were fairly tired, so we kind of just cuddled and
fell a sleep in each-others arms.

The first morning, I showed her the swimsuits and she
was excited but kind of uncomfortable that I had not
thrown in even one of her one-piece suits. She looked
a little bit leery of the three-triangle suit as she
held it, but genuinely seemed happy at the surprise and
that I had taken the time. We both put lotion on in
the room and headed toward the beach. When we got to
the beach and got settled, we both loved the view and
were so excited to have several days just for us.

I told her about the massage sessions and she said that
she did not know if she would like having another girl
rubbing oil on her skin. She tried to kind of back
out, but after talking about it and remembering a
couple of her friends telling her that they had one
before, she said it would be OK to try. We did the
usual lazy beach stuff and had fun rubbing suntan
lotion on each other. We headed back to the room and
ordered lunch. At 1:30 I told her I would take off and
walk the beach and that the girl doing the massage
would bring the table to the room at 1:45.

My wife seemed to relax, when she knew I was not going
to be there. I left and started toward the beach but
realized I had not brought the sun tan lotion. I
headed back and started to open the screen door on the
deck located on the back of the unit when I suddenly
saw a large very muscular black man setting up a
massage table in our room. I could hear the
conversation through the screen door and my head was
kind of spinning in confusion. I had not even thought
about a man doing the massage on my wife.

I could tell Cindy was really caught off guard as well
because he was going through his normal routine of
asking about anything that hurt, etc. I thought she
was going to tell him that she had changed her mind, by
the questions she was asking and the way she was
acting. When he had finished setting up the table, he
asked what she wanted to wear during the massage.
Cindy paused for a long time, and then asked what most
people wear.

He indicated that it just depended, some swimsuits,
some undergarments, some people want a towel only and
some do it nude. He indicated that any way was fine,
but that the oil can get on clothes. He said the oil
was similar to suntan oils. He also said that he would
only massage the exposed skin and that any motion could
be stopped at any time if it hurt or was uncomfortable.

She paused again and then quietly said that she would
stay in her swimsuit. My wife laid-down on the table
face down and he began the massage. I could not
believe I was watching this. The living area of the
unit was kind of sunken down, so I was 5-6 feet above
the table giving me a great view. My wife was really
tense as he went over her body. He was very
professional but I was still excited by the site.

He did ask if she wanted the straps off her shoulders
when he did them and she moved them off to the side of
her arms. She flipped over and he did the front. She
moved the straps off to her arms again and he did the
rest of her. It was like he followed the edge of her
swimsuit never touching it. It was still exciting when
he was doing her upper thighs and coming so close yet
not touching her intimate areas.

At the end he took her arms and kind of stretched them
across her body and then in a circle. Then he
stretched her legs, having her move her hips down to
the end of the table. He stood at the end of the
table, bent her leg up toward her chest, rotated it out
and around really spreading her legs, which gave me a
good view of her swimsuit bottom.

It excited me to know he was seeing her spread like
that. Well, he packed up and I took off back toward
the beach. I was filled with excitement that I really
did not understand but liked. When I returned about 30
minutes later. She seemed normal and had just gotten
out of the shower and finished getting dressed for

I asked her how she had enjoyed the massage and if the
girl was good. She said that she enjoyed it very much
but gave no indication as to it being a man that did
the massage. We had a great evening and Cindy was wild
in bed that night like it was our honeymoon, so I new
she had to have been at least somewhat excited as well
by the whole experience.

The second day I talked her into wearing the three-
triangle bikini but she wore shorts over it until we
got to the beach. We had a good lazy morning on the
beach and she finally got comfortable with the guys
coming by and taking, giving appreciative glances in
her direction. At 1:30 I again left and came back to
the screen door a short time later. He was already
there and I overheard Cindy call him Rolan. Rolan was
quick to set up the table and Cindy kept the triangle
bikini on.

He did the same routine but Rolan and Cindy talked much
more today about a bunch of general stuff. She
unhooked the tie at the neck when he did her shoulders
but tied it back before she turned over. He did the
front of her again following the edge of her swimsuit
but never touch her intimate areas. He asked if she
wanted the straps to the side when he did her
shoulders, she paused a second, then went ahead and
undid it but tensed up a bit. He massaged her
shoulders for a while and the top stayed covering her
but did move around some showing a little more of the
non-tanned part of her breasts.

I thought she would tie it back but did not. When he
took her arms and did the stretch at the end of
session, the top moved even more but still covered her.
Then he did the leg stretches. He did this even longer
today and seemed to really be looking at her bikini
bottoms, but all the while keeping the conversation
going. He packed up and left and when I came in she
was again coming out of the shower and was very happy.
We again talked a little about the massage but again
she did not mention a man was doing them.

The third day we spent the morning seeing sites and had
lunch. They had a free laundry service so we gathered
up a few things and I took them to the lobby to turn
them in at 1:30. When we counted them I noticed I had
both of her swimming suits. I went to pull one and
take it to my wife for her session, but got a wicked
thought not to, just to see what would happen.

I hurried back to the room and Rolan had not arrived.
Cindy was looking all over the room and in the
suitcases but there were no swimsuits. I felt like I
had really made the wrong decision. Rolan knocked at
the door and she let him in. He set up the table while
my wife went to the other room and closed the door. He
called for her when he was ready and she said just a
second. It was 3 or 4 minutes until she came out. She
came out in a robe turned way from him and kind of slid
on the table face down in one swift movement.

I could only see that she was wearing under garments
but could not tell exactly which ones. The massage was
the same except Cindy did not talk as much at first but
then continued the casual conversation like yesterday.
She had moved the straps to the side when he did the
shoulders same as the day before.

When he asked her to turn over she commented about both
her swim suits being washed and he just said that it
did not matter. She turned over and I saw that she had
worn one of the sets of under garments that were lacy
but not transparent. You could still see the outline
of her nipples and blond pubic hair though.

I was so excited because this was probably only the
second man to ever see my wife like this. The massage
continued the same and Cindy did move the shoulder
straps to the side the same as before. He really spent
a long time on her thighs, but it still did not look
like he was touching her intimate areas. The whole
time they were just talking casually. Then it
happened. Something I would not have believed if I had
not seen it with my own eyes. When he turned around to
get more oil, she quickly reached up and dropped the
cup on the bra just enough so that one nipple was
completely visible.

My cock instantly got hard.

When he turned around he was doing her stomach but I am
sure he saw the exposed flesh. When he went to the
shoulders and arms, he did them in the same order as
before. But when he came to the shoulder with the
exposed nipple, his hand gently moved low enough to
cross directly over the nipple. Cindy did not make a
move to say anything, only the normal casual
conversation. Cindy’s nipples are the most sensitive
area on her body so I knew she had to be really

Rolan’s touches were quick almost as if by accident at
first, but then were much more deliberate. When he
finished up with the shoulders he actually played just
with the nipple itself for about ten seconds. Rolan
did the stretches the same only her other nipple became
exposed but he did not touch it. When he stretched the
legs he really pulled her clear down to the end of he
table and spent a long time, watching her panties the
whole time.

Each time he did the leg stretch up to the shoulder he
would lean into her and today it seemed as though his
shorts were pressed directly up against the crotch of
her panties. I was so excited about today but she
again was getting out of the shower when I arrived and
acted as if nothing out of the ordinary had happened.
She was really crazy in bed that night though.

The 4th day she had her swimsuits back in the room and
I really felt she would wear one of them. She came out
in a robe again and when she quickly slipped onto the
table face down, I knew instantly what she was wearing.
Only one of the sets of under garments had transparent
material on the back of the panties, and that was the
one that she was wearing.

I could not believe what I was seeing my shy Cindy was
wearing almost completely transparent clothes in front
of Rolan. The massage went the same, but when Cindy
turned over I was so excited. Here she was in almost
transparent under garments that I had not even seen her
in yet. The massage was the same until he got to the
shoulders. When he turned around to get more oil she
undid the clasp that was between her breasts. As he
massaged her shoulders, the bra fell to the side
completely exposing her breasts.

She looked so beautiful, and it was not long before
Rolan was completely massaging her breasts and nipples.
All this time they are still having a casual
conversation. Cindy is really getting excited though
and had trouble continuing the conversation as she
normally would. When Rolan did her hips she commented
how good it felt and he said that if she wanted to
lower her panties he could get even deeper.

She hesitated, but then lowered them a couple of inches
and he worked on her hips. When he turned around to
get more oil she reached down and shoved them even
lower exposing about half of her bush. When Rolan
turned around even he was surprised. I noticed that
this time when he started doing her hips he brought his
shorts right on top of her hand that was palm down on
the table, all the while still carrying on a casual

Cindy pulled her hand back a little which he
instinctively massaged and placed it back on the table
palm up. The next time he leaned forward, he placed
his balls in her hand but she did not move her hand

He continued the massage but always left his balls in
her hand and after a couple of minutes I saw her hand
start slowly massaging them. His cock instantly got
hard and was visible through the shorts. He did the
stretches the same but when he did the legs the panties
were down so far it limited the motion but instead of
pulling them up he took them off. I could not believe
this stranger was staring at my wife’s pussy. As he
stretched her leg up to her chest he placed his shorts
right up against her.

The session quickly ended at this point and I was so
hard. I came back to the room as she was headed into
the shower, but instead we had wild sex then and there.
We both usually are not like that but neither of us
asked the other why.

The 5th and last day before we had to leave was one
that I was not sure what to do. I was afraid of what
would happen if she and Rolan had the final session but
was also excited to see what would. I almost stayed in
the room that afternoon but at 1:40 decided to leave.
I quickly came around and waited.

Rolan came in and set up the table the same as before.
Cindy wore a bra and panty set but those were removed
similar as before. As he did Cindy’s breasts she
commented she felt funny being naked in front of him.

Rolan kind of laughed it off and made an attempt at a
joke by saying that he had a couple of lady customers
that tried to talk him into getting naked as well but
that he would get fired if he took off his clothes. He
said one clever lady actually slid his shorts off of
him, which he said was out of his control. They both
kind of laughed.

Rolan went on in the same manner but when he started
doing her hips he again placed his balls in her now
waiting hand. She massaged them and again I could see
he became hard. Cindy then slipped her hand up and
started slipping his shorts down. Rolan just kept
talking about the island and what to see. She finally
had his cock completely exposed and the shorts slid to
the floor. Rolan was very large, thick and long. I
could not believe it.

My wife started slowly stroking him and I was going
nuts. Then he slowed stretched her arms the same as
before. When he moved her all the way down on the
bench to stretch her legs, I knew what was going to
happen. He positioned himself so that his cock just
touched her at first. Then he started to move just the
tip of his cock slowly in and out. He must have
continued this for ten minutes slowly going deeper and
then slowly stretched her leg up to her chest and drove
all the way in to her.

After a few quick movements Cindy came and Rolan shot
deep inside of her. I almost came with them. Soon,
Rolan started to put up the table and I quickly went
around to the front. As soon as he had left I came in
the door. Cindy was a little startled but had just
slipped on her robe.

I came over and gave her a kiss and she said that she
wanted to take a quick shower and then we could cuddle
but I held her tight and said I could not wait that
long. She was very tense that I would notice the come
inside of her, but I just quickly moved and inserted
into her. Once she saw I did not notice, she really
started to respond. I could not believe how wet and
loose she was from Rolan. It was too much for me to
handle, I came with only a few strokes. She just
commented that I had not come that fast in a long time.
She quickly darted to the shower.

Well, I have never told her what I saw that vacation
and I think it was just a one-time thing that happened.
It has definitely fueled both of our sex drives because
we have never been quite the same since that