Date: Wed, 19 Jan 2005 10:07:21 -0600
From: SW
Subject: The Advisor 4

After a night attending a gay orgy, and then coming home and fucking a
constantly horny college student, it's understandable that when I finally
woke up the next day my dick was sore. I puttered around my house naked, not
even wanting the feel cloth against my cock. Or maybe I just wanted to be
naked.

Actually, I didn't do much at all during the weekend. I had some work to do
and errands to run. Besides, the past few weeks of seemingly constant
fucking had left me pretty drained physically and emotionally. I did talk to
Josh during the weekend. We talked about the party and how we had both
enjoyed it. He said that William and Ken had called him and encouraged him
to bring me again. I appreciated being accepted.

During the weekend I had tried to call Kate to find out more about the
proposed spring break trip coming up in three weeks. However, she apparently
had a new boyfriend who no longer needed his brains because she was fucking
them out. Each time I called, Casey or Alexa told me that Kate was either
sucking his cock or fucking him till he couldn't walk. One time Casey had
held up the phone near Kate's bedroom door and I could actually hear their
grunts and groans. Casey and Alexa thought it was kind of funny at first but
by Sunday night it was getting to be a drag for Alexa trying to get clothes
and such out of the room she shared with Kate. Finally, late Sunday
afternoon the poor guy stumbled out of the room, and things pretty much
returned to normal.

I had a nice long conversation with Casey, the t-girl of the group. Although
over the past couple of weeks most of my sex had been with gay or bisexual
men, I still had a thing for Casey. We actually hadn't fucked in about two
weeks. She seemed OK with it when we talked. She did say that she had missed
spending time with me, but understood I was going through a time of
discovery. God, she was mature beyond her years.

After hearing that the stud had left, I went over to talk to Kate. "What's
the spring break deal?" I asked.

"OK. My grandfather worked on an ocean-going freighter during the 1930s,"
she said. "It mostly carried goods to the Yucatan Peninsula but also to
Central America. Anyway, one night on liberty he got in a card game in
Mexico. Some guy ran out of cash but put up the deed to a dot of an island.
My grandfather won the hand and the island.

"It's about half a mile off the coast of Mexico in what has been a fairly
remote area. It's starting to develop some now but is still pretty much
local. It's only about 200 acres from one end to the other. Over the years,
he remodeled and expanded the house that was there. Now it has four
bedrooms, a nice big living area, three baths and a small swimming pool. It
has a great beach on the ocean side.

"When I was growing up, my parents weren't too into going down there but my
grandfather and grandmother loved it and took me for weeks at a time.
There's a small village on the coast and I've gotten to know many of the
people there. My grandfather can't go anymore because of his age and health,
but he can't sell it. He says I will inherit it."

"That sounds incredible," I said. "He made enough working on ships to fix up
the place?"

"Oh, no. He only worked on boats for about 12 years, and then met my
grandmother and didn't want to be gone that much," Kate said. "He was always
good with money, though. He eventually became a real estate agent, saved his
money and invested it well. He was incredibly wealthy for a black man living
in the South. But he was well respected, even by the white people. He
retired at 55 and would spend six months a year on the island. When his and
my grandmother's health began to fail, they quit going down there."

We talked about cost of the trip. We would each be responsible for air fare
and part of the cost of groceries. Kate said she had also invited Josh, Mary
and Blair to go with us. That made six people. We estimated it could cost
about $500 each. Later, Casey and I went out for a burger. I could tell
something was on her mind and asked her about it. She admitted she wasn't
sure she could go on the trip. Her relationship with her family was not on
good enough terms for her to ask for the money to go, and she didn't have
enough by herself. I wasn't about to let her miss the trip.

"I'll pay the difference for you," I said.

"No, I can't let you do that," she said. "I really can't."

"Casey," I said, looking into her eyes, "I want to and I won't go without
you. You pay as much as you can, and I'll make up the rest."

"Are you sure you're not doing this because you feel sorry for me? I mean, I
want to go and all, but I understand that sometimes we can't do things we
want if the money's not there. I won't be crushed if I don't go."

"You're going and that's all there is to it," I told her.

We were sitting in a booth in a restaurant. She looked at me with watery
eyes. She smiled, leaned over and gave me a big kiss. I felt her tongue dart
into my mouth and it was like an electric bolt in my crotch. She pulled back
and said, "That's the nicest thing anyone has ever done for me."

We decided she would pay her part of the grocery bills, and I would purchase
her plane ticket and share of the van we would have to rent. After finishing
our burgers, as we got in the car Casey said, "Let's go back to your house."

We drove to my house. Casey walked in very casually. Went to the
refrigerator and got out a bottle of wine and poured both of us a glass. She
turned on some smooth jazz, turned off most of the lights and sat with me on
the sofa. We just sat there for a long time, talking some but mostly being
together. I had my arm around her and occasionally fondled her breast, but
we mostly enjoyed the quiet time.

After a time, she pulled my arm from around her shoulders but placed my hand
on her crotch. Through her jeans I could feel her hard-on. I fondled her a
moment, and then stood and, without saying a word, took her hand and led her
to my bedroom.

Once we arrived, I took her in my arms and kissed her deeply. Our tongues
intertwined and we both felt the heat building in our bodies. I pulled her
T-shirt over her head and began to suck and fondle her tits. We were still
standing in the middle of the room. I sucked each of her nipples to full
attention and then dropped to me knees and began kissing down her firm
belly. When I reached the top of her jeans, I unbuttoned them and eased them
over her hips. The jeans dropped to the floor, and she stepped out of them.
She wore bikini underwear and kissed all around the edges, licking some
places, kissing others. I turned her around briefly and planted kisses on
each of her ass cheeks.

She turned around again and looked down directly into my eyes. Without
taking my eyes offer hers, I pulled down her skimpy panties. I then looked
right at her hard, six-inch cock. I took it gently in my hand, then leaned
forward and planted a soft kiss on the tip. Casey gasped.

I put my lips around the very top of her penis and sucked gently and she
gasped again. I took another small amount of cock into my mouth and ran my
tongue around the ridge of her cockhead. I then began working more and more
of her cock into my mouth, gradually sucking harder and harder.

Before long, I was into full blowjob, bobbing my head up and down the shaft
of her she-male cock. Casey was moaning softly, whispering softly, "Yes,
yes. That feels sooo gooood. Oh, Dave, that feels so good."

Finally, Casey was ready to cum. I had been gently holding her balls and
felt them start to twitch. She didn't say a word, just starting spurting her
juice into my mouth. For probably the first time ever, I managed to take all
of it into my mouth and swallow it all. Not a drop leaked out. I was quite
proud of myself.

I stood and kissed Casey deeply. She began to massage my raging hard-on
through my jeans. I pulled away from her and guided her to the bed. She lay
down and watched as I did a quick strip. When I pulled off my jeans she sat
up as if to take me in her mouth, but I gently pushed her back onto the bed.
I found some lube and applied it to my cock and gently greased her asshole.
She pulled her legs back and apart as far as she could. I placed my cock at
the entrance to her ass and pushed in.

With little effort, my cock went balls deep. We lay still for a few seconds,
and then I began to make love to her. What I had been doing over the past
few months had been fucking. This, however, was something more. This was
intimate. This was two souls merging.

Thinking about it later, it had been similar to not the last time my late
wife and I had made love but to the last time we had been able to really
give ourselves to each other. It had been the most gentle and intense sex of
my life. We had made love after that, but it been more desperate; more like
trying to draw life from one another.

This time with Casey was giving. Every moment I made was complemented by
Casey. Every move she made fit perfectly with me. It probably actually
lasted just a couple of minutes, but it felt like hours. Eventually, my cock
began to strain and I knew I was about to come. I had not fondled her cock
much, but as soon as I began to spurt my cum into her ass, her cock jerked
and cum began to boil out the top and down the shaft.

When it was over, I lay on top of her for a few moments, then raised up,
pulled my cock out of her ass, and then licked her cum off her dick and
stomach. She snuggled in close together and fell asleep. As we drifted off,
she whispered, "I love you, Dave."

I simply gave her a squeezed and slept.

The next three weeks passed quickly as we made plans to spend spring break
on Kate's island. We had to purchase plane tickets and rent a van big enough
for six people and all our luggage for the three hour drive from the airport
to the village closest to the small island. During that time, Casey spent
more night at my house than her apartment.

Finally, the big day arrived. We gathered at the airport, got on our flight
and took off. The flight lasted about four hours. We got the van with little
trouble. Since Kate was the only one who had ever been to the village or
driven in Mexico for any extended time, she was elected driver. When we
finally reached the reached the village, we were all getting tired. However,
arriving gave us an andrenaline rush. It turned out Kate's grandfather paid
a family a small retainer to make a boat available for trips back and forth
to the island. The boat was waiting on us when we arrived. Our group and
luggage filled the boat, but we managed to all get in. It took about 30
minutes to navigate the half-mile out to the island.

It was great. On the shore side of the island was a small dock and boardwalk
up a slight rise to the house, which sat on a small hill. Josh and I lugged
most of the bags to the house. While not ready for House Beautiful, it was
roomy and comfortable. Kate assigned bedrooms. Casey and I in one, Kate and
Alexa in another, Josh and Mary in the third and Blair alone in the fourth.

The view from the house was great. The small hill where the house sat gave a
nice view of the ocean on both sides. The widows were big with open shutters
and screens. The beach was on the ocean side. It was about 100 yards long
and maybe 25 wide with beautiful white sand. Even though it was late in the
day, we all walked down to take a long and all decided it was perfect.

We went back to the house. The refrigerator was fulled stocked with food and
beverages, thanks to Kate's grandfather. We found some chicken in the 'frig,
so Josh and I volunteered to grill out on the deck overlooking the beach.
Before long we were all chatting excitedly as we ate chicken, salad and
vegetables.

We retired to the deck as night drew closer. All of us, except Blair, had a
glass of wine. As the sun settled into the western horizon, Kate took the
floor. "OK, here are the ground rules," she said. "First, now arguing. We're
here to have fun. If somebody bugs you, take some time alone. No. 2, take a
turn cooking and/or cleaning. We can call on help from my grandfather's
housekeeper, but I'd rather not because of the third rule.

"The third rule is that bathing suits are optional all week. Now, before
anybody asks, yes, I cleared it with Josh, Mary and Blair. If you want to
wear a suit, fine, but if you don't that's fine, too. Last year, the three
of us came down by ourselves and we were naked all week. Any questions?"

Nobody had any. We sat and talked for another hour or two before folks began
to yawn. I saw Casey stifle a couple of yawns and suggested we go to bed. We
said good night and went to our room. We had a big room with a king bed and
walk-in closet. We had already unpacked, so we stripped and get in bed. We
snuggled close and talked softly for a long time. The window faced the beach
and a cool breezed blew in through the screen.

During our quiet times, I thought I heard something. I whispered about it to
Casey and we started listening closely. sure enough, we heard the sounds of
people having sex. Trying not to giggle, we began picking out individuals
based on the noise they made. We soon picked out Alexa and Kate. Casey said
that she could tell that Kate was diving into Alexa's pussy. We also figured
that Josh was fucking Mary from behind by the tell-tale slapping of his
thighs against her ass. They all came within a few seconds of one another. I
figured they all heard each other, at least subconsciously. Not to be left
out, I took Casey's hard cock in my hand and she took mine in hers and we
jerked off each other. Poor Blair was the only one not getting any.

We woke to a postcard morning. I got up and pulled on some shorts and a
T-shirt and went to the kitchen. Josh and Blair were already up eating
cereal. I poured myself a bowl, and Casey soon joined us. The other three
came in over the next half hour. The women, including Blair, had on skimpy
bikinis. Alexa's was a thong that showed off her excellent ass. We joked and
talked for about a half hour, and then Kate showed us where the beach chairs
and towels were stored. We all grabbed a chair, a couple of umbrellas and
put some drinks in a small ice chest and made for the beach.

As soon as everyone had staked out a spot, the women began taking off their
bikinis. I had to admit it was quite a site, three fine-bodied women taking
off all their clothes without hesitation. Casey and Blair stripped off their
tops, but didn't take off their bottoms. Casey leaned over and whispered
that she should go nude since Blair was there.

Blair had really nice tits. They had the perkiness all teen girls seem to
have, standing almost straight out with hard nipples. I noticed that Blair
kept stealing glances at the other girls, including her mom.

Josh stripped off his shorts and shirt and stretched out naked on a beach
chair – with a nice hard-on. "OK," he said, "this is all going to take some
getting used to, all these naked and half-naked hardbodies around."

Having been self-conscious about my own growing hardness, I joined Josh and
took off all my clothes.

We were all close enough for easy conversation but separated enough for a
smidgen of privacy. I looked up from the book I was reading and saw Mary and
Blair talking. Blair was nodding her head as Mary appeared to question her.
My curiosity aroused (behind my sun glasses), I watched Mary go talk softly
to Josh. The talked for several minutes. Mary had squatted next to Josh's
chaise lounge chair, which opened her pussy nicely, so the view was quite
good. After several minutes, Mary stood. Josh took a sip of water, and then
he stood, too.

"Folks," he said. "Gather round. We have something important to say and do."

We all turned our attention to Josh, Mary and Blair. "Blair has made an
important decision. She's noticed that as everyone undressed, some seemed a
bit uncomfortable around her," Josh said. "She appreciates your concern, but
wants everyone to feel free to enjoy themselves completely. Therefore, Blair
is going to go nude, too.

"This will be a special moment for all of us, and when she takes off her
bikini bottom you'll know why."

With that, Blair stepped up on sturdy wooden chair. Josh and Mary stood on
either side of her, their fingers holding strings at her hips where the
bottom of her swimsuit was tied. "One, two, three," Josh said, and then he
and Mary pulled the strings.

Blair's bikini bottom fell away to reveal – a cock! Blair was a t-girl.

Casey jumped up and ran over to Blair and hugged her tightly. I was stunned,
as were Kate and Alexa. But they quickly recovered and also hugged Blair.
This was indeed a big moment as what we thought was a teenaged girl was
sharing with us that she was a guy.

After the initial reactions, everybody basically returned to what they had
been doing. Blair gave each of her parents a big hug. Casey moved her chair
over close to Blair's, and they began talking softly and giggling. They had
a special bond.

I had to admit, Blair was damn fine looking. She had exposed those nice tits
and now I learned she had a nice cock, too. It appeared to be about the same
size and Josh's, although maybe a bit thicker.

We pretty much enjoyed the sun until lunch time, then most of us went up the
house for sandwiches and to cool off a bit. Blair and Casey stayed a bit
longer, talking. Then after Casey had eaten a sandwich, she went with Blair
to Josh and Mary's room, closed the door and talked to them for several
minutes. I figured she was just passing along some wisdom of her own
experience and didn't worry about it.

That afternoon, the six of us sunbathed and swam in the ocean naked as
jaybirds. It was really quite freeing. Soon, Josh and I were able to be
around four hot women without constant hard-ons. I wasn't sure if that was
good thing or not.

We cooked out again that night, and again retired to the deck to watch the
sunset. Being in the sun all day had drained all of us, and folks began
making their way to bed early. Shortly after Casey and I had gotten to our
room, Josh, Mary and Casey came in.

"What's up, guys?" I asked.

Mary began. "Blair has obviously taken a bold step today," she said. "We
want to start by telling you her story. Early on she had more feminine
characteristics than male. Her situation became more difficult as she got
older. She wanted to be a girl. When Josh got the job he has now, Blair
asked if she could live as a girl in the new town. We finally agreed and
began raising her as a girl. We found a doctor who was willing to give her
breasts appropriate to her age and every couple of years, they are adjusted.



"That's understandable," I said. "It appears everything's working out fine.
I'm sure Casey would be willing to sort of mentor you."

"Yeah, that would be cool," Blair said and blushed.

"Dave," Josh said, "telling your Blair's story isn't the only reason we
wanted to talk to you. Blair has started attracting some interest from boys,
and, well, she's ready for her first sexual experience. She, and we agree,
would like for that to be with you."

I looked at Blair, who again blushed deeply, but held my gaze. "Shouldn't it
be with someone else?" I said. "Don't get me wrong, but shouldn't her first
time with some guy she's got a crush on?"
"Blair?" Josh said and looked at her.

"I want you. I know you are a sensitive person and will be gentle and
loving. I know you are bisexual and that makes a difference, too," she said.

I thought for a minute, and then said, "Well, if that's what you want, I'm
willing. I have to admit it's a little strange for me."

Everybody smiled, and Mary said, "We understand, but Josh and I know you
well. We trust you."

With that, everyone left the room except Blair. We sort of looked at each
other and then she giggled nervously and sat on the bed. "Well!" I said
because I didn't know what else to say. I walked to the bed and sat beside
her.

"You've got a guy you're interested in?" I asked.

"Yes," she said.

"Does he know about you?"

"I think he suspects. I've sort of dropped a hint or two."

"Is he OK with it?"

"I think so," she said. "He's virgin, too, and we've been friends a while. I
think when he finds out he'll be OK."

As we talked, I put my arm around her. After a few minutes, she looked up at
me, gently pulled my mouth down to hers and kissed me. Our tongues tangled
quite a bit and I felt my cock harden. I reached up and began to massage her
tits through her t-shirt. She wasn't wearing a bra and her nipples were nice
and stiff. I gave each a light pinch and Blair shivered.

As we kissed harder, we fell back on the bed and I ran my hands under
Blair's t-shirt and fondled her tits. They were a nice size for a
16-year-old. I felt my cock getting harder and harder in my shorts. I pulled
Blair's t-shirt over her head. I licked and sucked her tits. Her nipples
felt good on my tongue and when I lightly bit them it sent shock waves
through her body. I continued sucking her titties and ran my hands up and
down her back, getting closer and closer to the top of her cutoff jeans,
which barely covered her ass. I ran my hands all over her hard, smooth ass,
slipping them under what was left of the legs of her shorts. I ran my hand
down her ass crack.

Finally, I gently pushed her onto her back and, still kissing her mouth and
tits, unbuttoned her shorts and reached inside. She worked her shorts down
to her knees, while I grasped her hard cock. It felt good in my hand, hot
and eager. Most of her pubic hair was shaved except for a strip right above
her dick. I ran my hands down between her legs and hefted her balls. She
moaned.

I then started kissing down her abdomen, working my way closer and closer to
her cock. Just as I was about to reach the tip, I lifted my head and asked,
"You've never had your cock sucked?" She just shook her head no. I dropped
my head back down and put my mouth right up to, but not quite touching her
cock. I let my hot breath blow onto the head of her cock, where precum was
already oozing. She gasped and her cock jerked toward my mouth. I slowly put
my lips around the head and ran my tongue over the slit at the top. Blair's
body stiffened for a moment, and then relaxed. I gently sucked just above
the rim of her cockhead for a moment, and then took a bit more into my
mouth. Again I stopped and ran my tongue all around the rip of her cock's
head, letting her get used to the feel of my mouth. Slowly I began working
my way up and down the shaft of her cock. In the meantime, I gently massaged
her balls.

Blair was moaning and gasping. I felt her hand on the back of my head and
figured that, like most first-timers, she was about to cum. I swallowed as
mucho of her seven-inch dick as I could and increased the pressure. As I
bobbed on her cock, I shortened the distance down the shaft I went until I
was basically just sucking the head. Blair lost it.

With a scream, she tried to push my head down (I was ready for it), but I
held firm and sucked on her cockhead as hard as I could. She began spurting
cum into my mouth and down my throat. I sucked until she begged me to stop.

As I stretched out next to Blair on the bed, she said, "Oh, my god. That was
incredible. Is it always like that?"

"No," I said with a smile. "You got extra effort."

"I'll bet you always suck that good," she said. "I just know it."

I sat up and took off my shirt, and then stood to take off my shorts. "Let
me," she said and reached over and unbuttoned the khaki shorts. They dropped
to the floor and my cock stood at attention, almost hurting it was so hard.

She took it in her hand and began stroking it. "Like this?" she asked. "Not
quite so tight," I told her and she loosened her grip a bit. "That's very
good," I said.

She stroked me for a moment but I was so hot from getting to take her cherry
that I knew I wouldn't last long. She then looked up at me and asked, "Do
you want me to suck it?"

"Yes, very much," I said.

"How do it do it?" she asked as she licked some precum off my slit. It was
hard to believe she really knew nothing about giving a blowjob but I said,
"Sort of like drinking a milkshake through a straw. Use more tongue than
teeth, more lips than tongue."

She looked up me and smiled, and then dropped her head back onto my dick.
She took it into her mouth and began sucking. She didn't take much into her
mouth, but that was OK with me since it was her first time. She worked her
tongue around it some, allowed some saliva to coat it and sucked hard. As I
suspected, it didn't take long.

I felt my nuts tighten and without thinking, pushed her head down so that my
cock was down her throat. I began to spurt and she began to gag. I quickly
pulled back and my third and fourth spurts shot onto her face. As my
twitching cock began to subside, more of my cum landed on her throat and
tits.

"Sorry," I said when I had recovered. "I should have warned you I was about
to cum."

"That's, OK. Did I do all right," she asked.

"You did great," I said.

We lay on the bed next to each other sort of catching our breath. Finally, I
asked her, "Why me? Really."

"Well, I sort of have a crush on you, but I know you like Casey. I've heard
you talk about her and seen you together. I guess I decided I wanted you to
fuck me the day I saw you fuck Mom. Even thought it was kind of just a wild
fuck, I could tell you really wanted her to cum; you didn't want to just
shoot off in her and leave. I don't know, that got me kind of hot," she
said.

Fortunately the light in the room was low because I think she was a tad
embarrassed but wanted to say it. I pulled her into the crook of my shoulder
and she lay her head on my chest. We lay like that for a few minutes, and
then she began to fondle my cock. It responded and I felt her cock harden
against my leg. She continued gently rubbing and squeezing my dick, until I
had a full hard-on.

She looked up at me with innocent eyes and said, "Dave, will you make love
to me now?"

I didn't say a word, simply pulled her up to my mouth. We kissed deeply, and
I rolled her onto her back. I went to the dresser for some lube. When I
turned back around she was lying on the bed with her heels on the edge of
the bed. Her balls were on display and I could just see her ass. I stood so
she could see me, squirted some lube onto my hands and began greasing my
cock.

"This might hurt a little bit," I told her, "but I'm going to go slowly. If
it hurts too bad tell me and I'll stop moving, but I'm not going to pull
out. If we're going to do this, let's go all the way. Understand?"

She smiled and nodded.

I stepped to the bed and lifted one her legs bit higher and pushed back
gently. Her asshole was now more exposed. I put the tube of lube against her
ass and said, "I'm going to squirt some lubricant into your ass so it will
be easier."

"OK," she whispered and I squeezed the tube. "Oh, that's cold," she
exclaimed.

"Yeah. Never figured out why its always so cold," I said as I dropped the
tub and began tearing open a condom.

"No," she said. "Don't use that."

"Are you sure?"

"Yes," she said.

I dropped the condom and took her other leg in my hands just below her knees
and pushed them back. She reached up and held her legs back and apart. I
took one hand down and positioned my cock at her asshole.

"OK, the key is to relax as much as you can. Have you fingered your ass
before," I asked.

Blair nodded. She looked a bit nervous so I tried to give her a re-assuring
smile.

"So you know how important it is to relax. Now, it also helps if you kind of
push down, like you're taking a dump. Ready?"

She nodded again and I pushed gently forward with my greasy dick. She
stiffened when it first began to push in, but took a deep breath and relaxed
and part of the head of my cock entered her ass. I didn't move for a few
seconds, and then began pushing some more. Her face scrunched up as if in
pain and I whispered, "Take deep breaths. Try to relax." She took a deep
breath and as she exhaled, my cock slid in a bit father. God her ass was
tight.

"You doing OK?" I asked and she nodded again.

Once again I began to slowly ease my cock farther into her ass. Finally, I
pushed past her sphincter and my cock slid into the balls. Neither of us
moved for a moment.

"I'm not a virgin anymore," she said with a smile. "I've got a nice cock up
my ass. I'm a real t-girl now!"

I smiled at her, feeling the pressure of her tight ass ring around my cock,
which was buried as far as it would go. "You're doing great," I told her.
"That actually was easier than I thought it would be."

"It hurts a little but not too bad," she said. "Besides, I want this, so
that makes it easier. Will you start fucking me now?"

"You got it," I said and began gently pulling back, and then pushing
forward. I couldn't have been moving more than an inch or two, just slightly
moving my hips. Blair seemed to like it, though. She lowered her legs just a
little and I reached down and began to stroke her now rigid cock. "Oooohhh,
that feels so good," she said.

Her ass was really tight and the heat of the room began causing me to sweat.
It did feel good and my strokes got slightly longer. I fucked her for a
minute or two longer and then, almost without warning, began shooting cum
into her ass. Since I had already cum once, it wasn't a big load, but she
felt and it liked it. When I stopped cumming, my cock was still wedged in
her ass. I slowly pulled back and it popped out. "Ooooo," she cooed when it
left her ass, stretched and open.

Her cock was very hard. I didn't want to waste much time, so I picked up the
lube and began putting it on her cock. It was hard to not simply jerk that
hard meat, but I wanted it my ass. When I had slathered her dick with lube,
I climbed up on the bed, got on all fours and handed her the tube.

"Put some in my ass and then fuck me," I told her.

She jumped up and put the tube against my asshole. She squirted in some lube
and then put her cock against my ass. "Just try to do like I did with you,"
I told her. She pressed forward, and I felt her cock begin to enter my ass.
Since I had a little (but not much) more experience, I was able to relax and
it didn't take long for her to push past my sphincter and slide her cock all
the way up my ass. She began stroking gently, but I was ready to fuck. I
began moving my ass back and forth. Her thighs began slapping into mine as I
moaned, "Fuck me good." She increased her rhythm a bit and a minute or two
later shot a big load into my gut. Like most teens she had plenty to shoot.
She pushed hard into my ass and froze as the cum shot out of her balls and
into my ass.

We both collapsed onto bed, me on my stomach and Blair on top of me with her
cock up my ass. After a minute or two she stirred and slowly pulled out her
cock. I felt her cum run out of my ass and onto my balls.

"Oh my," she said as she laid down next to me. "That was wonderful. Thank
you so much." She kissed me and gave me a big hug. We both giggled, and then
lay quietly. Eventually we drifted off to sleep.

The rest of the week was spent being lazy and fucking. By now, everybody was
fucking everybody else. After losing her cherry to me, Blair fucked Casey
the next afternoon, then Kate and then Alexa. It was as if she got started
and couldn't stop. We just sort of joked about it and let her go. I'm sure
her parents would have a talk with her about being a bit more discriminating
when they got back to the States.

One afternoon Kate and I were the only ones on the beach. "Daaavvve," she
said in a little girl voice from behind a book she was reading, "my pussy's
wet."

"It is?" I responded.

"Yeah. I think it needs to be licked," she said.

"Probably."

"Daaaaave. Will you lick my pussy?"

"Weeelll," I said then almost dove between her leg as she lay in a chaise
lounge beach chair. I licked and sucked her to a strong orgasm. As I
finished, Mary came down to see if we wanted anything to drink. She had a
beer in her hand and was naked.

"Shit," she said. "That must have been some good sucking."

"It was," Kate said. "Dave could be a lesbian."

"Here," Mary said handing me the beer bottle. "Take a drink and suck my
cunt, too."

Which I did. By the time Mary almost crushed my jaws with her thighs as she
came, my cock was about to explode. When I stood up, Kate got on all fours
on the sand and Mary did the same, offering me their pussies, or asses, if I
preferred. I didn't have the strength to ease my cock up an ass. I plunged
into Kate's pussy, slammed her a few strokes and then moved over to Mary's.
I slammed her cunt once, twice and then starting pumping cum. I cried out
loudly as I emptied my balls.

When I was done, Kate and I ran into the water, but Mary said she would wait
and walked back up with my cum running down her leg. I later learned that
she dragged Josh into their bedroom, let him licked my cum off her legs and
out of her pussy, and then fucked his brains out.

Also during the week, Josh and I found time to enjoy each other's bodies. We
had one fivesome with me, Josh, Kate, Alexa and Mary. However, the rule was
you could only fuck your same gender. It was hot, sitting in the living room
of the island house watching three women fuck each other while another guy
stroked my cock, eventually sucking me off. I sucked off Josh, too.

One night we went to the local cantina and had a great time. It got a little
on the wild side when Alexa had one margarita too many and tried to blow
some guy on the dance floor. "Cock! I want cock!" she started shouting. We
hustled her (and the guy) out the door, to the boat and back to the island.

We tried to sit around and talk, but Alexa made too much noise fucking her
guy. So we all went to our own beds. Kate slipped into Blair's room. By now
Blair had gotten cock from me and Casey and pussy from Alexa and Kate.

Finally, the day came to pack up and leave. We packed our clothes, stored
away the beach chairs, towels and other items and thoroughly cleaned the
house. Actually, our return came at the right time. My dick was getting
sore.

When we arrived back at our homes, we discovered a tragedy had struck. Two
nights before, fire had hit the apartment complex where Alexa, Kate and
Casey lived. It had gutted an apartment in their building and their
apartment had sustained minor damage. They didn't lose anything, but they
were forced to move out. Kate and Alexa called a friend who had room for
two, but not three. As we gathered Casey's belongings, she wondered out loud
where she would live.

Without giving it any thought, I said, "Move in with me." As soon as I said
it, I knew it was the right thing. She looked at me with a huge smile. "Do
you mean it?" she asked. I paused and said, "Yes, I mean it. I'm not just
saying because of the fire. I mean, if there hadn't been a fire, I don't
know if I would have suggested it this soon, but, well, I want you to move
in."

Casey ran across the room and hugged me tightly. A few weeks before, I had
finally packed away all of my late wife's clothes and things. I wasn't ready
to give them away, but I was ready to share the dresser again.

Kate and Alexa were also excited. We moved Casey's things to my house,
storing most of it in boxes in the garage until we figured out what was
need, what was not and where things would go. That night we slept in my bed,
arms around each other but too tired to make love.

Then next day when I got home from work, Casey was in the house wearing a
t-shirt and a sexy pair of jeans. She had a candle-light dinner ready. We
ate the meal with some soft jazz playing. After it was over, Casey stood and
did a slow strip tease for me, finally turning her back to me and bending
over as she slid thong panties down her great legs, pushing her ass toward
me. She slowly turned around so I could see her cock standing hard and
proud. I stood, picked her up and carried her back to the bedroom. We then
fucked until we couldn't. I fucked her, she fucked me, we fucked each other.
We finally collapsed into each other's arms, too tired to move. As I fell
asleep, I pulled her close to me. He ass pressed against my cock. It didn't
stir. It couldn't. I slid my hand down to her cock and gave it a gentle
squeeze.

In just about six months, I had gone from straight single man to bisexual
living with a college-age t-girl. I couldn't wait to see what the next six
months would bring.