Date: Thu, 14 Jan 2016 15:59:03 -0600
From: Jack Parke <letsdothedeedagain@gmail.com>
Subject: Rick and Bob (tt, mm, TG, TV, oral, anal)

Rick and Bob/bi
J Parke <letsdothedeedagain@gmail.com>


I've been an avid reader of the stories posted on Nifty for a number of
years.  This is truly a unique site and provides some great times form the
wonderful stories that are uploaded to it.  It also provides a venue for
authors to publish their stories, which may never see the light of day
anywhere else.  I would urge you to consider making a donation at
http://donate.nifty.org/donate.html so we can enjoy this site for a long
time to cum.

This story is pure fiction. It's about sex between teens, sex between
adults but not with each other, and not across the age gap. It also has
spanking play it in. If any of this bothers you, or it's not legal where
you are, just hit the `delete' button and be gone!

I love feedback so feel free to comment about the story and/or the writing
style. I ignore all spam but love hearing constructive criticism from
everyone! Let me know what you think... <letsdothedeedagain@gmail.com>



My name is Rick, I'm 15 years old and a sophomore in high school. I grew up
in a normal family; mom, dad and a younger sister, Jen. Dad had a full time
factory job as a supervisor and mom worked part time to help with the
family's needs. But this story is about some strange things that happened
to me the past few years.

When I was in grade school, I was kind of a loner. I played with the boys
on the playground at school; we played soccer, basketball and baseball
during our lunch period and also in PE class. But after school, I kept to
myself. I didn't have any real friends, just a few casual acquaintances. My
athletic skill was wanting, I wasn't coordinated enough nor was I as
competitive as the jocks were for the win. I was an average student, got
mostly Cs and sort of "slid" through grade school. After I got out of
there, I was enrolled in junior high, 6-7-8 grades. But this is where I
want to "introduce" Bob into this story. Bob was the same age as me and we
were classmates through grade school. Bob, or Bobby as many called him, was
smaller than I was and rather thin. He had a long face and his hair was
very dark, shoulder length. Thinking back now, I guess he was actually cute
but at the time, I didn't see it. Bobby was smart, he was at the top of the
class academically and excelled. A lot of the kids didn't like him because
we reasoned he killed the "curve" when our teachers graded us. So even in
grade school there were nerds!

When we got into middle school, it was a confluence of 12 schools so there
were a lot of new faces. My grade school class only contributed 8 boys,
some had moved away and others to different schools. So in my first home
room, I saw, and sat next to, Bobby. We hadn't talked much "back then" but
I said "Hi" to him and he returned the greeting back. As we had 15 minutes
before class, I asked "so what did you do over the summer?"

"Nothing much, me and my two brothers went to the Grand Canyon on vacation"
he said, "but it was a long trip driving and we're all glad to be home."

"I didn't know you had two brothers, are they older or younger?" I asked.

"They're both older, one is 16 and the other is 18. John is in high school
and Evan is going to the local junior college here in town. So what did you
do this vacation, did you go anywhere?"

"Not much, I went camping and fishing with my family. Dad loves the outdoor
tent stuff so we took a one week trip to the national park and got a huge
tent and we camped. It was a pain, my little sister Jen is a brat and
scared all the fish away!"

That's about all I remember of our "first" conversation. The year got
started and we shared a US History class and the teacher had us triple up
and do a few projects, I made sure to include Bobby in my group as our
grades were better for it. Things went on about the same over the next year
also and then after 7th grade, Bobby's dad was killed in an industrial
accident and they moved away.

As I think back now, I remember starting to wonder about Bobby, he didn't
seem to grow as much as I was growing, he kept to himself and I think I was
only at his house four or five times, and only for a project. But I
remember he acted sort of effeminate and our conversations stuck to the
matter at hand and never into sports or whatever he was into doing;
basically we never got past being just academia acquaintances.

I remember I was racing into puberty and found all sorts of "new" things to
do! My 3½ inch cock, which later grew to a nice 5 inch cock was cut and
was the most fun thing I had ever discovered! I had a couple of school
buddies and we exchanged notes on what we were doing, albeit all made up,
and what we'd like to do to "her"! Or her. Or her!! And then one day
towards the end of my last year in middle school, dad came home and
announced he was being promoted and we were moving. We moved of all places,
to London for a year. Holy cow, did that open my eyes to a plethora of
things in humanity! I went to an "American school" so my education was on
track with what the kids in the US were doing but we also had a lot of UK
kids share the classes with us. I met up with a few of them and we used to
run around together, and get the Bobbies after us too!

One time we wandered into the SOHO district and did I get an education!
Gays are very fluid in London and are accepted, not like in the USA. I got
to see what I learned were men in drag, prostitutes, pretty well whatever I
might have wanted to see. We talked to a young girl and asked why she was
there, she informed me, by taking my hand and putting it down the front of
her shorts, that she was a shemale and that's how she supported herself. I
was springing a boner about then and she asked how much money I had, so we
decided £5 was enough and I got my first blow job! It didn't take her
long, after all I had seen, I was primed and ready! After she was done, she
said "thanks Yank, I hang around here and maybe you'd like to try my pussy
next time? Just £10!" We left and I never saw here again but it made a
strong impression on me. I wasn't gay but I had just shot my load of cum
into another boy; I liked girls but the shemale had made an impression on
me and began to question my feelings towards the gay or "other" parts of
our society.

After a year had passed, my dad was transferred back to the US, only in a
bigger city but still in the Midwest. I enrolled in a high school that had
close to 900 kids and was like a little city amongst itself. I had the
usual classes and found myself a little popular since I had spent a year in
the UK. But one day as I was walking to a class, I noticed someone that I
thought I knew but couldn't place. It was a cute, short girl, light colored
hair you could tell was dyed but still not too hard to look at. She saw me
and smiled but then looked away. I didn't think too much of it for a few
days until I found we shared a social studies class. The girl's name was
Bobi and during a lab one day, I went up to her and introduced myself to
her.

"Hi Bobi, my name is..." she cut me off saying, "Rick"; my mouth dropped
open and started at her.

"Do I know you? I mean, you know my name!"

"Rick, my name was Bob or Bobby, back in grade and middle school. We did a
few projects back then. A lot has happened to me the past couple of years;
it's just nice to see someone I know. You were always nice to me when the
others picked on me and I don't have any friends here at all."

I was dumbfounded and just stared at her! Finally I found my mouth start to
form some words and said "what happened to you?" I was almost stuttering
but got out, "would you tell me?"

"Yes, can you come home with me after school?" and I replied I would. I
called my mom and told her I was going to meet up with an old friend from
the old place and she said fine and to be home around six for dinner. After
school, I got on the same bus as Bobi and rode to her stop but I stayed
away from her, I didn't want anyone to know I was with "HER"! The bus
dropped the two of us off and away it went. She looked me in the eye and
said "I'm not going to bite! You don't have to be afraid of me!"

We walked to her home, a very nice place, way above the style or luxury I
lived in. We went in and she got us both a soda and we sat at the kitchen
table, facing each other. She could see the questions on my face and began
by explaining all that happened. She said that after her dad was killed,
there was a `substantial' (later learned it was multi million) damage
payment made to her mom for their safety and well being. She went on to say
"you can also see I'm a girl too. Or at least I live as a girl now. When I
was born, I was a boy and I have `boy equipment' but I know, in my heart,
I'm a girl so that's how I live now. Mom was upset but we talked about this
and she said she had some knowledge of boy/girl `confusion' and allowed me
to lead this life. She used to take me shopping and she helped me pick out
pretty clothes and we had a lot of fun!" She continued, "After we moved
here a couple of years ago, both my brothers were in college and my mom
said that she would invite `her' sister out for a visit. I was sort of
shocked, I didn't know she had a sister, I had heard she had a brother."

"Mom's sister, Salvatore is, or was, actually her brother at birth. I never
met him as a child, mom explained that he began to dress as a woman and has
lived that way for a long time and loved the entire life style as being a
woman. Anyway, a couple of weeks later, `Aunt' Sally flew out for three
weeks and it was the first time I ever met `her'. I always knew of her but
we never met, even at any family gatherings. I guess the rest of the family
wasn't as accepting as my mom was of her `sister lifestyle'. Anyway, Aunt
Sally was very nice to me and we had a lot of deep discussions of what I
was going through and she explained about the changes I would be going
through."

"So what happened, how did you become a girl? Did you just start wearing
girl stuff, I can see you have boobies, and they are nice, (with a big
grin) but did you just switch one Monday morning?"

"No, it's not like that. Mom took me to a psychiatrist downtown that
specializes in gender issues. She wrote a prescription for hormones to help
start me growing breasts, which took close to a year to get to my smallish
C cups I have today. I still have my penis and it works just like yours
does, it gets hard and I can make it shoot off, just like you do. But I
love being "Bobi" and love being a girl."

I just sat there, looking at her. She had a tear run down her cheek and I
leaned over and took it on my thumb, drying her face. She then asked "can I
ask you to not tell anyone that I used to be `Bob'? I don't mix with the
school groups, I keep to myself and my school work. Mom has a academic
coach working with me and I plan on going to college but not sure what I
want to major in but I don't date, I'm scared I'd get found out that I'm a
`queer boy in drag' and that'd ruin me."

"Mom has been talking to a lawyer about my gender, I don't have any
`official government IDs' as yet but if I want to drive, I'll have to state
gender when I get a driver's license."

"Bobi, I'm not going to say anything to any of them. I've known you for
several years, we sort of grew up together and you sure did help me with my
school work stuff `cause you're so damn smart!"

She gave me a huge grin and reached across the table and took my hands into
her hands and I have to admit, that gave me some `stirrings' in my
crotch. I took a good look at her, she was cute, maybe 5'6", 100 pound if
she was soaking wet, nice tits and a very nice round ass. Just about then,
her mom walked in the door and I got `THE LOOK' from her!

"Mom, this is Rick, we went to grade and middle school together. Do you
remember we used to get together and work on some of those assignments back
then?"

"Yes, how are you Rick?" I could tell she was working things out in her
head and Bobi was bubbling on about having a real friend!

"I'm fine Mrs. Blakely, I saw Bobi the other day and she looked like
someone I knew and we finally talked today. She told me about what she has
been going through and it doesn't matter to me; as long as she helps me
with my school work, I'm cool with whatever she wants to do."

The three of us sat around and talked for a couple of hours, I told her
about living in London and she asked what all I had seen! I didn't tell her
about the shemale that blew me but did mention how fascinated I was with
the SOHO district and she grinned ear to ear so I was sure she knew I had
done some `exploration' while I was there. It was getting close for me to
go home and she offered to drive me and we all jumped in her car and she
drove me home. Bobi and I decided to be friends in school and that ended my
day.

As time went along, Bobi and I worked together on a few projects and she
helped me with my grades. As this was a huge high school, none of the
coaches were looking for someone like me to play any sports so the jocks
left me alone, Bobi kept to herself and I continued in my `loner'
personality from when I was young. The `word' going around was that we,
Bobi and I, were a couple and everyone left us alone. But I'll never forget
our first kiss!

We had been assigned to write a story for English and since I had lived in
London, we decided to use that as the premise of our story. I went home
with her one Friday afternoon after clearing it with mom. Bobi got us sodas
and we sat around in her family room, trying to decide on what stories we
were going to tell. We finally decided to tell my story on going to the
American school and have Brit students in the class amongst us and the
funny things that developed from that. We were sitting side by side at the
table as I was making notes and she asked me a question about something and
our faces were real close. She was looking me right in the eyes and we just
sort of leaned over and tenderly kissed each other. She broke the kiss and
pulled back about a foot, still not saying anything but looking me in my
eyes, I took my hand and pulled her back towards me and kissed her again,
only a little more aggressively. I felt her lips part and knew what was
going to happen, I wasn't an expert at kissing but I had kissed a few girls
in the past and knew what a French kiss was.

I felt her tongue on my lip and opened my mouth, inviting it in. We kissed
for several minutes with our tongues battling each other and exploring our
mouths. Bobi broke the kiss and she said "I've wanted to do that for the
past couple of months. I hope it didn't freak you out" and that's when I
realized I had just kissed a guy! I also realized I was as hard as a rock
too.

"Thank you Rick, I needed that. I don't have a boyfriend and I consider you
my boyfriend, if you want a girlfriend. I hope you can accept me as a girl,
can you?"

"Yeah Bobi, I can. I know I sure did enjoy the kiss, hell, I got hard from
it!"

She laughed and said "can I ask you a question?" I nodded yes and she said
"have you had sex with a girl yet?"

My face got as red as a firetruck! She started to giggle and her eyes told
me she knew the answer. "Who was it? Did you date her? Where did you meet
her?" I finally told her it was a girl in the American school and we had
oral sex. I didn't tell her it was a shemale and that I had paid her for it
either!

The next few months, we became boy/girl friend with each other. We went to
the school games, dances and school parties together; held hands like young
kids do and enjoyed each other's company. Bobi's mom was happy we were
together and I began to spend more and more time with Bobi. Finally one day
my mom asked what was going on and I told her I had met a girl and liked
her. She said if we were at a function and her parents were there, that I
was to introduce her to them and I agreed. I was a little worried, I didn't
know if she knew Bobi was actually Bob, or if she even remembered. I was
really surprised that my brat sister, Jen really liked Bobi and pestered us
to take her with us when we went out.

It was in March that Mrs. Blakely had planned to make a trip for a week to
visit her other sister over family matters. She called her `sis' Sally to
come and stay with her but Sally suggested Bobi fly to her house and stay
there. It was spring break and it would be a fun time for her to see where
her `aunt' lived. Bobi and I didn't want to be apart but finally Bobi's mom
decided to see if I wanted to go with her! I was up for it, so was Aunt
Sally, who knew the story between us, but I had to work on my mom. Aunt
Sally lived in New York and Bobi's mom talked to my mother and told her it
would be a good educational experience for both of us kids and that her
sister would ride herd on the both of us; mom agreed and I packed my bag
and away we went!

Aunt Sally picked us up at JFK and whisked us away to her condo. I had seen
a few pictures of Aunt Sally, she was about 5'8", maybe 120 pounds, nice
tits, fantastic ass and long dark hair. She was a very good looking woman,
even to a 15 year old, she was HOT! Aunt Sally was LOADED and it showed,
the condo had to cost a fortune, it was a four bedroom 2500 square foot
place with a restaurant, gym, pool, room service staff for whatever you
might want, basically a self contained city within the city. As soon as we
got there, she had the doorman take the bags up to her apartment and took
us to the restaurant as it was close to dinner time. I wasn't too hungry
but Bobi ate the hell out of a NY Strip steak! As I sat there eating, I
realized it was three guys that were going to be together for a week and
started to feel my groin stir awake!

When we got upstairs, we were shown to our bedrooms which shared a `jack
and jill' bath and I understood that this might be a monumental opportunity
for the two of us! We got unpacked and met Aunt Sally in the living room
and had a desert of pie and ice cream plus sodas. Aunt Sally had a scotch
or two and got very mellow. Then she dropped the bombshell and asked "have
you two had sex yet?" My mouth dropped and Bobi grinned ear to ear! I began
to stutter and all I got out was a "no" and Bobi started giggling!

"Aunt Sally, you scared Rick to death! We've done a lot of kissing and he's
played with my boobies and I liked it!" Then the second bombshell...

"Well you've got an adjoining bathroom and I don't plan on going into
either of your bedrooms while you're here. You do what you want to do!
There's lube, toys, most anything you want in the bed table in each bedroom
so enjoy yourselves" and with that, she said she was tired and was going to
bed, and, `poof' and she was gone!

I was sitting on the couch next to Bobi, overlooking Central Park and
looked deep in Bobi's eyes and smiled, she leaned over and we began
kissing. The view overlooking Central Park was beautiful and very romantic
and as we were kissing I began to rub her tities, I could feel her nipples
getting hard, as was my cock.

She suddenly jumped up and pulled me by the hand and led me to her bedroom
and sat me on the bed. She did a strip tease for me, slowly taking off her
clothes. When she was naked, her cock was sticking straight out and this
was the first time I'd seen it. It was a little smaller than mine, maybe 4
inches long and very thin. We had been chaste with each other at home,
other than her rubbing me a little and me feeling her tits, nothing had
occurred. But now I was presented with a hard cock! "You know, this is the
first time I've seen you naked, you do have a nice cock!"

"No Rick, it's not a cock. Us girls call it our `clit', it's kind of the
same thing that real women have. It feels good, like a woman's clit does,
and when a woman has an orgasm, she has a lot of fluids come out of her
pussy and when I cum, I have cum fluids that comes out of my clit!"

Bobi came up to me and started pulling my shirt off, over my head. My mouth
was at the perfect level to take her nipples in my mouth so I placed my
hands on her hips and drew her close to me, allowing me to suckle on her
nipples and caressing her nice bottom. This caused her hard clit to touch
my stomach and I could feel it was wet and sticky with precum!

She then got on her knees and took my shoes and socks off, then rose up
before me and started unbuckling my belt. Then she opened my waist button,
lowered my zipper and had me push up so she could pull my pants and
underpants off. I sat there with a hardon half way to Jersey and it was
leaking precum like crazy.

Next she had me stand and she turned the bed down, lay down and led me to
lie beside her. We started to make out like crazy and she started stroking
my cock. I told her to stop, I was going to shoot and she did. I kissed my
way down her neck to her tits again and sucked on them and at the same
time, stroking her clit with my hand. She held my head and directed it from
side to side, all the time moaning. I think it was right then that I
realized what I had to do next and kissed my way down the rest of the way
and kissed down to her clit. She didn't have any pubic hair, it was as bare
as a baby's butt. I kissed the end of her clit and slowly took it in my
mouth and she shook like she was having a seizure. I ran my mouth up and
down, paying special attention to her glans with my tongue as I fondly
recalled the blow job I had in London and how good it felt! I was stroking
her balls with one hand and rubbing her bottom, her legs were raised and
wrapped around my back and neck. My mouth was very wet and spittle was
leaking down her clit, over her balls onto her perineum region. I took a
finger and got it wet and put it on her boi pussy, pushing a little and the
finger went in to the first knuckle.

"Oh my gawwwwdddd Ricccckkk, I'mmmm gooonnnaaaa cummmmm..." I felt her
clithead swell and she jerked a couple of times and then froze and she shot
a strong load of cum in my mouth! I don't know what told me to do it but I
swirled her juice around in my mouth on her clit and as she shot more,
swallowing what I was unable to have room for in my mouth. She finally
started to shrink in my mouth and she pulled me up beside her and gave me
as deep a kiss as I've ever had in my life!

She broke the kiss and looked me in the eyes and said "I love you Rick, I
wasn't sure for a long time but I know I love you so very much."

"I love you too Bobi, we are a perfect couple and I want to be with you
forever!"

"Baby, lay back and let me return the favor you just gave me. I laid back
and Bobi kissed her way down my body but not before paying special
attention to my nipples, which I found rather sensitive and it felt
good. She made her way down and slowly gave me a blow job that almost made
me pass out as I shot my load in her mouth. She came up beside me, gave me
a peck on the cheek and we fell asleep holding on to each other.

The next morning, we made our way to the kitchen in our bathrobes and found
Aunt Sally making breakfast. We sat round the table, ate scrambled eggs and
sausage, toast, coffee for Aunt Sal and juice for Bobi and I. she asked if
we both slept well and the both of us blushed and it told her all she
needed to know! After breakfast, Aunt Sally told us she had plans for us
and to get a shower, and we'd do some sightseeing. We walked back to our
room(s) and realized the shower was big enough for both of us so we jumped
in, showered and got dressed and ready to go.

We had a fantastic day, Aunt Sally took us to see all sorts of things I've
only heard of. We had a leisurely lunch and ended the afternoon with a walk
in Central Park. The entire time, Aunt Sally sounded like a guided tour
director, pointing out things to see and told us she had tickets for a
couple of days later to a Broadway show! On the way back we stopped in the
restaurant and I had a piece of cow that would normally feed a platoon of
Marines! And then we went back up to her apartment. Aunt Sal told us to get
in our bathrobes and we'd try something new. When we returned, Aunt Sally
gave us a cup of what looked to be coffee, I've had coffee before but it
was only so-so to me but this was really tasty. It was a rich blend with a
shot of good bourbon in it; we sipped it and sat on the floor in a circle,
talking.

"I know you two finally `met up' last night and have discovered each other
but I want to give you a little instruction on other things you can
do. Have either of you ever fucked anyone or been fucked?"

I went beet red but Bobi said "no, but Rick put his finger in me last night
and it felt beyond anything I've ever felt in my life!"

"Sweetheart, that's great!" then looking at me, "Rick, you need to be very
careful when you fuck your girlfriend. You can do a lot of damage to her
`pussy' but if you're careful, she'll love everything you do for her. I've
been fucked a million times and I love taking a nice cock in my pussy, it
makes me feel so much like the real woman that I am!"

She stood up and went to a drawer and came back with a small velvet bag
with several items inside it. She sat back down, opened the bag and pulled
out a smallish, thin dildo. "This is what you should start with, you get it
well lubed with the KY jelly and after you get a nice dollop of jelly in
her pussy, you push this in real slow." She looked directly into Bobi's
eyes and continued, "it will hurt a little when it first goes in but your
man will help you by stroking your clit."

I know I had a questioned look on my face and she said "Rick, Bobi's cock
is her clit, women have clits and they feel real good when played with and
especially when you kiss them. You push this dildo in and out, real slow
and she'll relax. As long as you take the time, she'll be ready for
you. How big is your cock? Here, pull your robe apart!"

My face went red but she pulled my robe apart and exposed my now hard cock,
"Baby, you're going to need the second dildo in you before this guy fucks
you, it's large!!"

She continued, picking up a second dildo, "Rick, get this one lubed up and
work it in, but only after she is comfortable with this smaller one. Take
your time and I swear to you, she'll be ready to take your cock and you can
breed her. And sweetheart," looking into Bobi's eyes, "you take this one
and while you're sucking his cock to get him ready, you put this in him and
he'll love you for it, just make sure it's well coated with lube and you
should get a finger lubed up and put it in first. It's the best way to make
love!" She was holding up a slim, curved item with a small bulb on the end
of it. She told us it would massage my prostate.

Then looking at me she said "and Rick, there's no reason she shouldn't put
her clit in you, it's a lot smaller than yours and I swear, you'll enjoy
having her pussy juice in your bottom!" (more blushing!!)

While all this was going on, we had had two more coffees and it was close
to midnight. Aunt Sally told us it was time for bed but as she got up, she
looked us both in the eyes and told us "feel free to play with the dildos
but don't actually do any fucking. I have a plan to make that first time
the most romantic time either of you will ever have in your lives! Oh, I
have to take care of some business tomorrow so I'll be gone all day. Enjoy
yourselves but stay here, don't try to go out on your own. I'll be home
around 4 and Bobi, you and I need to do something special, just between us
girls! Then tomorrow night we are going to an off-Broadway play with my
special friend Bill... goodnight!"

Bobi and I walked to her bedroom and I was asleep on my feet. The three
shots of bourbon had hit me like a ton of bricks. I lay down beside her, we
kissed each other and both fell sound asleep. The next morning, we got up,
walked to the kitchen and found a note for us to call room service and
order our breakfast, and we did. It was delivered rather quickly so we sat
and ate and chatted about what we were going to do all day.

"Bobi, I love you and think I really want to have `real' sex with you. Why
don't we take a shower and get out the toys your aunt said are there and
experiment?"

"Sounds great Rick, I'm excited to have you `pop my cherry' and hope it's
soon! I've talked to some of the girls at school and they've asked me if
we've fucked yet and I told them no, but hoped it would be soon. Most all
of them have been `bred' by their boyfriends and I want to be like them!"

We went upstairs, showered and flew into the bed! Bobi found the dildos,
lube, a long slender curved one with a small bulb on it (for me) and we
spent the afternoon experimenting with how they worked. When I put the
small dildo in Bobi the first time, she said it hurt and to pull it out! I
jerked it out real quick and she said to put some lube on my finger and put
it in real slow. I did and she seemed to relax and it went in without
giving her any pain. Then when I put in the dildo, I had a lot of lube on
it, and pushed it in real slow. As the dildo head popped through her
sphincter, she said to stop and let her get used to it, and I did. When she
said she was ready, she told me to push it in real slow, and I did. It
didn't take long and she wanted the slightly bigger one so I repeated what
I had done with the small dildo and it didn't take long and she said she
was going to cum. I immediately lowered my mouth on her clit and she shot a
load of gurl jism in my mouth. Then she got the slim one and did the same
to me, when she hit my prostate, I shot a load of cum in her mouth, I damn
nigh drowned her!

We finally quit playing around 3 and watched some TV for a while and then
as expected, the door opened around 4 and in walked Aunt Sally with a man I
had not seen before. She introduced him as her `friend' Bill and said he
was taking us to the Broadway show tonight. Bill was a good looking guy,
smartly dressed in a suit. He stood close to 6 foot, maybe 200-210 pounds
and what looked to be good shape. He had dark hair and the start of a 5
o'clock shadow that looked good on him. Let me put it to you this way, I
wouldn't have messed with him, he looked like he could handle himself and I
would rather have him on my side!

We sat around for a few minutes and chatted, Bill told us he was a stock
broker on Wall Street and enjoyed the theatre and found a show he felt
teenagers would enjoy. Suddenly, Aunt Sally jumped up and said "Bobi, come
with me!" took her hand and poof, they were gone. Bill and I talked about
sports, the football Giants v Jets, and I was able to talk with him, he was
about as much a sports fan as I was, not much but enough to talk to a
client about the subject.

Aunt Sally and Bobi were gone for close to an hour and then Bobi came back
in a robe and told me come with her, she said Aunt Sally wanted us to get
ready to go out as we would be having an early dinner. I joined her and
asked "What were you and Aunt Sally doing?"

"It's a woman's secret but I got to see her bed, it's huge! It's bigger
than king size, it's round and her bedroom is beautiful. We took our
showers, got dressed and joined Bill and Aunt Sally in her living room.

Bill had a car waiting for us, we went to a steak house and had a great
meal and after that to the Broadway show. It was a fun show, all about the
bleachers in Wrigley Field and I really enjoyed it. After that, we headed
back to the condo and got there around 9:30 and went up to the apartment.

Aunt Sally poured everyone a drink and we sat around and talked about the
show. Then she changed the course of the conversation saying "Bobi, as I
told you earlier, we are going to make this the most memorable experience
of your sex life you'll ever have! Bill and I are going to introduce you
both to some new things and hope you enjoy what you see and what happens."
Saying that, she stood and took Bill by the hand and indicated for us to
follow, and we did, to her palatial bedroom.

A side note here, I had noticed one thing, the entire evening, Aunt Sally
had behaved like my little sis Jen did, she was a consummate, but fun,
brat. She poked fun at Bill and us also, nothing really cutting but just
little short verbal jabs about anything and everything. I found it funny,
she was putting on quite she `floor show' and we had a fun time.

As we entered the bedroom, Bill asked us to sit on the edge of the bed and
said he had some `business' to take care of. "Sally, get that chair from
your dressing table and put it right here!", indicating where he was
standing. "Now, get that hairbrush off your dressing table and bring it to
me!"

"Oh no Bill, are you going to spank me? In front of the kids? Oh please
Bill don't do that, it will hurt!"

"Sally, you have been a brat all evening and you are going to pay for what
you have done. These kids need to learn there are consequences for their
actions and they are going to see how it's handled; maybe if Bobi gets
snippy, Rick might need to handle things for himself too!"

I was too excited to blush, my cock was straining in my pants. Bill had
Aunt Sally stand before him and he pulled her pants down to the floor,
followed by her lace panties and we could see her bottom. Then he told her
to remove her blouse, "spankings are given to naked, recalcitrant, naughty
people!"

"Oh please Bill, please don't make me get naked in front of the kids, it'll
be too embarrassing!"

"Nonsense Baby, you don't have anything the both of them haven't seen by
now!" And with that, off came the rest of Aunt Sally's clothes. Then he
turned her sideways to us and slowly pulled her over his lap. I noticed
that Aunt Sally's clit was sticking straight out so she was excited.

Bill began to spank her, it was apparent to me from the few spankings I'd
received as a kid, this wasn't really a punishment spanking. When his hand
would fall on her bum, she would let out a small `whimper' but nothing much
else. He spanked her for a while and then stopped and stroked her bottom
which allowed her time to recover. Then he leaned over and grabbed the
hairbrush and I knew the real spanking was about to start!

Aunt Sally's bottom was pink as Bill raised the hairbrush and as it struck
"SMAACKK", Aunt Sally yelped "AAIIIIEEEE, That hurt! Please don't do that
again" only to be followed by "CRRAAACKKK". "YYEEOOOWWWWW, PLEASE NO MORE,
THAT HURRRTTTTTTT..."

Bill responded "Baby, you know a spanking has to hurt to be good and this
is going to be good so hang on, you're going to pay for being a brat all
night!"

Bill spanked her for close to 15 minutes; he would spank her with the
hairbrush then stop for a minute and stroke her bottom, then start all over
again. Aunt Sally was crying real tears, we could see them go down her
cheeks and fall from her nose to the floor. While all this was going on, I
was holding Bobi as close as I could and began to stroke her crotch as I
could feel her clit growing. I was as hard as I had ever been in my life
and we began deep French kissing while we heard Aunt Sally take her
spanking. My hand was inside her slipover shirt and she simply took it off
and unfastened her bra. She also pulled my shirt up and off and we both
unfastened our pants. By the time the spanking was over, we were both
almost totally naked and Bill was the only one with clothes on. Bill helped
her up off his lap and had her kneel in front of the chair where he
sat. She knew exactly what was expected of her, Aunt Sally unfastened his
pants, allowing his hard cock to stand out.

Aunt Sally began to suck on Bill's cock and it was apparent he was really
enjoying what she was doing. Bobi and I were no longer watching but what we
were hearing was so exciting I felt we would both cum soon.

Bill stood up and when he did, his cock fell from Aunt Sally's mouth. He
told her "get the special cushion, I'm going to breed you tonight. You've
been a total brat and this will be part of your punishment!"

"In front of the kids?"

Bill smacked her ass and it was a hard swat, I could see the outline of his
hand on her ass cheek. Aunt Sally got a cushion, about two feet wide and
four feet long and it was apparent if she lay over the top of it, it would
put her bottom in a raised position. Bill stepped forward and had her lie
on it, there were Velcro strips to secure her legs apart and her arms at
her side.

"Rick, when a woman has been naughty, like Sally, sometimes it's necessary
to `put them in their place' and that's what I'm going to do. I'd suggest
you watch and maybe we can do a bit more when I'm done."

By this time, both Bobi and I were totally naked and my cock was oozing
precum, as was her clit. Bill got behind Aunt Sally, took a dollop of KY
jelly and put it in and around her pussy. Then he lined up and with a quick
push, ran his cock in her pussy. The only thing we hard was the sound of
skin on skin and Aunt Sally moaning. By this time, I had my lubed finger in
Bobi and knew this would be the night we would both lost our
virginity. Bill was driving in and out of Aunt Sally and it wasn't long and
he suddenly drove in as deep as he could and held his place. I could see
his balls were drawn up and his ass cheeks were quivering. I could also
hear Aunt Sally moaning and whimpering for him to `fuck her' and I saw her
clit start pumping its white juice down the side of the cushion. Finally,
he plunged forward and let out an "AAAIIIIIIIIII I'M CUMMMMMIIINNNNGGGGGGG"
and I could see him shaking as he drove his jism into Aunt Sally's pussy!

When Bill was done, he slowly withdrew and asked me to let Sally up,
meaning to release her bondage strips holding her in place for her
breeding. As I did, I could see the white cum leaking from her and I put my
finger on it and ran it up and down. Aunt Sally jumped a little and then
said "Oh my gawd, rub that for me!"

As I did that, Bill dropped on his back on the bed, face up with a huge
smile on his face. Aunt Sally pushed herself up, grabbed a towel and sat
next to Bobi on the bed and hugged her. Bobi had tears in her eyes and
asked "did that hurt? It looked like you both enjoyed it when he was
fucking you. Did the spanking hurt? Oh Aunt Sally, I'm scared!!"

"Quiet child, it was wonderful and I loved all of it, especially the
spanking! Bill gave me an erotic spanking and you need to learn there is a
fine line between pain and pleasure and that spanking was pure pleasure!"
They continued to hug and then Aunt Sally put her lips on Bobi's and they
enjoyed a deep kiss which made me get harder than I already was!

She continued, "Bill is a gentle lover and so very kind to me. Please relax
and let things happen, you remember what we talked about this afternoon?"
Bobi gave an affirmative nod... "Let this go the way it needs to go and I
promise you'll enjoy what is going to happen next!!"

Bobi was sniffing her nose and I gave her some tissues and she blew her
nose. Aunt Sally told me to come sit next to Bobi and give her a lover's
kiss, which I did. I noticed Bill was up on an elbow, watching and taking
in everything that was happening. I didn't know what was going to occur but
I was sure hoping I was going to get to fuck Bobi!

Both Bobi and I were hard, we had been kissing, fondling and I had kept my
finger in Bobi's pussy for the past half hour. I could feel her `pussy
muscles' holding my finger in place and I was ready to do more! "Bill, lay
down..." Bill laid flat on the bed with his legs together... "Bobi, lay on
top of Bill, facing him..."

"I don't understand Aunt Sally, what do you want me to do?" I could see the
fear in Bobi's eyes, I think she knew what was about to happen and she was
terrified it was going to hurt. I know from some of our conversations that
she said she had heard from her friends how much getting fucked would
hurt. I leaned over and gave her a tender kiss and when we broke, I held
her face in my hand and told her that I loved her and would never hurt
her. She smiled back at me and said "I know you won't hurt me Rick, but
please be gentle!"

"Baby, Bill is going to cuddle you for what's about to happen. Rick is
going to take your virginity but it will be easier if he enters you from
the rear. So lie on Bill and allow him to help you with this."

Bobi laid down on Bill, he gently held her to him and was whispering in her
ear little things like `it's doing to be OK baby', `let this happen, you'll
love it'...

Once Aunt Sally had Bobi on top of Bill, she placed Bobi's legs on either
side of Bill's legs; "Bill, spread your legs apart" and that caused Bobi's
legs to be flayed very wide! Then she took my arm and led me to kneel
between Bobi's wide spread legs. I knew I was about to lose my virginity
and I was leaking precum like it was running out of a full open faucet!

Aunt Sally produced a handful of KY and slowly stroked my 5 inch cock,
placing it at the entrance to Bobi's boi pussy. I was ready to just `stab'
it into her, but Aunt Sally held me back. She was whispering in my ear what
to do... "Baby, rub your cockhead on her rosebud, take your time... Bobi,
remember what I told you today, push like you're trying to take a bowel
movement..." I noticed Bobi move a little and her pussy lips `winked' at
me, I was so ready to enter her!

My cockhead was at her pussy lips and they `winked', I pushed forward
slightly and my head popped inside her! Bobi let out a `yelp', I had hurt
her and I didn't want to do that! But she went quiet as Bill slowly stroked
her back, whispering comforting platitudes in her ear. I stayed there with
just my cockhead beyond her sphincter, allowing her to get used to its
intrusion. Then she lifted her head from Bill's chest, turned and looking
at me said "go ahead Rick, push it in but go slow."

Aunt Sally still had my cock in her hand but she removed it and laid her
hand flat against my abdomen, she put her other hand on my ass and very
slowly allowed me to enter Bobi. It took four or five minutes for my cock
to go in but I felt my balls resting against her as I bottomed out. Bobi
had been gasping slightly, I knew to take my time and when I was all the
way in, I said "Bobi, does it hurt?"

"No baby, but just hold it there until I get used to you being inside me!"

"I will sugar and I love you so very much!"

"I love you too and thank you for taking my virginity and my cherry!!!" As
she said that, I slowly began to pull back, being careful to not pull all
the way out. When I was at the end, I waited for a minute and then slowly
began the trip back to the bottom of her pussy. Once there, I waited a
minute and then began the trek back to the start. The feelings I was
getting from her pussy walls were indescribable, I could feel her tighten
her pussy (I later learned she had been practicing `Kegel' exercises) and
then relax it.

I'm not sure how many times I went in and out slowly but I felt a `lump' in
her pussy and recognized when my cockhead went past it, Bobi gasped but I
could tell the gasp was a pleasure gasp! After five or six trips, she let
out a gasp and then said, in a demanding tone, "FUCK ME RICK!!! FILL MY
PUSSY WITH YOUR COCK!!! GIVE IT TO ME!!!" That's all it took and I began to
fuck her in earnest.

Every time I pushed forward, the feelings were growing so fast that I felt
I was going to cum! Bobi was writhing on top of Bill, he was holding on to
her for dear life! As I would lurch forward, I would let out a
"UGGGHHHHHH", stop and repeat it again. I knew I was close but suddenly I
heard Bobi...

"OH SHIT, I'M GOING TO CUUUMMMMM... FUCCKKK MEEE RICCKKK... PPUUMMMPPP
YOOUURRR SEEEEEDD IN MEEEEEE... OOHH MMYYY GGAAWWDDDD... II'MMM
CCUUMMMMMIIINNNGGGG..." and Bobi shot her cum all over Bill's chest!

And that's when I felt Aunt Sally insert the curved toy, it hit my
prostate... I could feel Bobi's pussy walls massaging my cock and that's
when I lost it... my cock felt like it grew two inches and then suddenly,
"IIII'MMMM CCCCCUUMMMMMMIINNGGGGG" and I flooded her pussy with my cum. I
wasn't counting but I think I deposed a gallon of my love juice inside her,
I had never in my life felt anything as good as what had just happened!!

I lay on her back, gently stroking her hips as my cock began to shrink. It
fell out and I fell on my side, still holding her hips. Bobi lifted herself
up from Bill's chest and lay, facing me, with Bill on her back side. Aunt
Sally lay facing me so the four of us were lying on the bed, slowly
fondling each other after this great event. I looked Bobi and told her "I
love you baby, I want to be with you forever!"

"Rick, we're young but I know I love you, you have been so good to me for
the past few years and I love you for that. Please don't ever leave me!"

I woke up the next morning after a totally sated rest, and saw my baby
lying beside me on her back, softly breathing. I leaned over and kissed her
softly on her lips and hey eyes opened and she smiled. I lifted myself up
on my elbow and said "good morning love. How did you sleep?"

"I slept better than I ever have. I love you so much, Rick. I want you to
fuck me every chance you get!"

I chuckled and pointed to the wide cushion Bill had used to fuck Aunt
Sally, the two of them were up already and one of them had set the `magic
cushion' on the bed, I wondered if it was a suggestion? "Want to give it a
try?"

"Are you going to spank me too? Please spank me, I want to see what Aunt
Sally felt last night. But please don't spank me hard!" with that, Bobi got
up on the cushion and lay down. "Please fasten the Velcro strips to hold me
in place, I really want to feel what it feels like to get spanked.

Well who was I to refuse that hot request? I got up, grabbed the `dreaded'
hairbrush. I walked over next to where the cushion was and put her legs and
arms in place. Then I began to pat her bottom, very lightly. But she lifted
her head and told me to "get busy, do it right!" And again, who was I to
refuse such a hot request. I began to land the hand smacks harder and
harder on her bottom, I could see her bum getting pink and I knew she was
feeling it.

"Owww baby, that hurts. Please don't hit me so hard. Plllleassseee Baby,
that hurrrssttttt." I ignored it and remembered what Bill had said to Aunt
Sally so I responded with "Baby, a spanking has to hurt to be good and I'm
going to make this a good one!"

I spanked Bobi for quite a while, after my hand started to hurt, I picked
up the hairbrush and Bobi really started crying and pleading with me to
stop. She was getting louder and louder and I wondered if the entire
building heard her! But finally I stopped and walked over to Aunt Sally's
makeup table and grabbed a tube of Aloe Vera lotion and began to apply the
cooling lotion to Bobi's red bottom. "Oh Rick that feels so good! Oh Rick,
put some in my pussy. It needs to feel you again... Please hurry!!!"

I put a dollop on my finger and plunged it into Bobi's pussy, then I coated
my cock and lined up my cock with her pussy. As soon as my cockhead touched
her pussy lips, I saw them `wink' at me and pushed forward. I entered her
easily and waited but after just a few seconds, Bobi told me to plunge
in. "Fuck me Rick... I want to feel you pump your seed in me!!!" I fucked
her for less than two minutes and I lost control and pumped another huge
load inside her! I couldn't believe how lucky I was, I had a loving
girlfriend and a partner. As I withdrew, I released Bobi from the cushion
and we heard applause from the bedroom door jamb where Bill and Aunt Sally
were standing. They were in bathrobes and smiling like Cheshire cats!

"Well, well, well, I see you two are up! And I see you found the cushion we
left for you to try, we loved watching all you kids did!! But I see one
thing we still need to do" Aunt Sally said as she walked towards the bed. I
was kneeling on the bed and Bobi had gotten up and was standing next to me
displaying a hard on (she hadn't cum during our tryst!). As Aunt Sally got
there, she took my arm and forcefully `directed' me to lie on the cushion
and very quickly fastened the Velcro strips, holding me in place!

"Bobi, Rick," she paused, "Bill and I enjoy a very satisfying relationship
but it is built on trust. And from time to time, both of us `mess up' and
have to pay the piper for our actions. Rick, you just spanked Bobi for
nothing she has done and that, young man, is inexcusable. So Bobi," handing
her a leather paddle, "here's an implement you need to use on Rick's
naughty behind! You need to turn his bum nice and red and then fair play
says you need to breed him yourself!"

I could feel my face getting beet red, I was as embarrassed as I had ever
been in my life. But things were happening fast and all of a sudden a loud
"CRACK" and I grimaced, I didn't make a sound, I was tougher than she
was!!! I felt a strip of `fire' across my ass cheeks, it burned and hurt
like hell! "CRACCK" again and I kept my teeth tightly locked, not emitting
a sound. "PPOOOPP" and I yelped! "Damn it, that hurt!" I said. Bill sat
down at my head and was massaging my neck, I heard him whisper "Son, you
need this, it hurts but what follows is going to be the most absolute gift
you'll ever receive when she's done working your ass over!"

But damn it, it really hurt. My ass was on fire and I began to openly
sob. But the spanking didn't end, Bobi kept on delivering those horrible
swats on my bottom and then she moved to the back of my thighs! Holy shit,
that REALLY hurt! And my legs were parted and she addressed the space
between them and that was worse yet. It was finally over but I was still
bawling my eyes out. I had NEVER been spanked like that in my life. My
parents had spanked me a time or two growing up but it was two or three
swats and then it was over. It hurt but nothing like this. Suddenly I felt
something cool and recognized someone was applying a lotion to my obviously
bruised, most probably bloody, bottom. (I checked later, not a bruise or
cut!)

I opened my eyes and Bill was gone, I couldn't see behind me but the
application of lotion continued. Then I felt the application to go my balls
and cock, it was a smaller hand so I knew it was Bobi applying the crème
and she really knew how to make me feel good. Not a word was said and I
felt her middle finger sink into my ass, I knew I was going to feel her 4
inch cock in my ass and I was going to lose my virginity to her.

Fortunately for me, Bobi's cock was smaller than mine. The hormones she had
taken had stopped her clit from growing past its 4 inch, ¾ inch thick
size. She had a cut clit and I loved sucking it, it fit easily in my
mouth. Still with nothing being said, I felt the head of her clit at my
rosebud and she easily inserted it in. The pain level was minimal; it
actually felt good when she pushed it forward.

"Oh baby, that feels so good!!! Ram it in me, keep going, oh yeah, fuck me
harder!" She did, she got into her rhythm and began to lunge forward after
each retreat. And every time she went in, she massaged my prostate and I
was loving that! I had just cum less than a half hour earlier when I fucked
Bobi when she was on the cushion so I was just `along for the ride' until I
heard her say "II'MMM CCUUUUMMMMMIIIINNNNGGGGGG!!!!"

I felt her clit swell and then felt the warm flow of fluid in my bowel. She
gave a few more lunges and deposited more and more of her juice, it was
great. And then all of a sudden, I shot a load down the cushion, there had
to be another gallon of my jism dribbling down that cushion! It felt so
damn good.

Suddenly, it was all over. Bobi pulled out, released me from my bindings
and we laid side by side, kissed each other tenderly and fell asleep. We
didn't sleep long and woke up, put on a couple of bathrobes we found and
headed for the living room. We found Bill and Aunt Sally sitting there,
both totally nude! Aunt Sally got up and put on an apron and led us to the
kitchen and fixed us some breakfast. The clock showed us it was 1pm
already, the entire morning had been used up!

We spent the rest of the day playing with Bill and Sally (she had insisted
we call her `Sally' and drop the `aunt'), we really had a fun time. Bobi
told me that Sally had given her a douche the previous day, she said that
the douche would clean out the pussy for a gurl's lover and she said it
wouldn't hurt me to have one once in a while if we were going to swap
fucks!

A few days later, we got off the plane at Ohare and found Mrs. Bartlet and
my parents standing by the luggage claim, all smiling like crazy. We all
hugged, gathered our bags and headed for our respective cars. As we were
going out, my dad had his hand on the back of my neck and chuckled and with
a `knowing voice' said, "you dog you!"

This all happened a long time ago. We both graduated from high school, Bobi
at the top of our class and me making the upper 50% of the graduation class
possible. Bobi went on to college, got her degree and then on to law school
and took a prestigious job with a top Chicago law firm. Me? I went to trade
school and became an electrician, rising to General Foreman on construction
projects.

During our vacation in New York, Bobi's mom's attorney found a genial Cook
County judge who signed an order changing Bobi's legal gender from male to
female which solved a lot of Bobi's concerns. We dated for many years and
after Bobi got the job with the law firm, we married and are living the
good life... the sex, spanking and loving is all great... and frequent!