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My Girlfriend's Girlfriend free porn video
My Girlfriend's Girl Friend
Although this is fictional, many parts of this story actually happened.
You, the reader can decide for yourself which are real and which are
entirely a lifetime crossdresser's vivid imaginations.
My name is Don. This story takes place in the late 60's when everyone had
a little different or new view of their sexuality.
From the time I was able to masturbate, I was in my mother's lingerie
drawer trying on her silky panties and hose. I was probably 12 or 13 and
took great pleasure trying them on and feeling that orgasmic sensation
against my hardening dick. I'd first put on hose that actually had seams
up the back, which would later become one of my finest pleasures. They
didn't have thigh-highs back then, so to keep them up you needed a
girdle or garter belt. I had tried on girdles several times but they were
way too restrictive for what I was doing. So, I chose a garter belt. The
garter belt was a bit too big, but a safety pin took care of that issue.
I next would pull on a pair of Mom's silkiest panties. The feel of them
going up my stocking encased legs would nearly put me over the top. The
best was yet to come (pun intended)...I'd lie down on my bed and move the
head of my cock back and forth against the nylon...stopping just short of
cumming. I'd be leaking pre-cum like crazy, all over the front of the
panties, but I wouldn't stop until I had my orgasm. I can't remember when
I first came, but I do remember that the cleanup became a problem after
that.
As I got older and in grade school, a good friend of mine would come over
to the house after school and we'd have jerk-off sessions. We did this
almost every day and it became a ritual for years. We used old Playboys,
even Sears catalogs at times to give us a visual thrill to get things
started. We once decided that it would be fun to jerk-off the other guy
and after that a new chapter opened in my life. I once wore stockings and
panties for him and he had a good laugh...so much for dampening my ego.
By the time we were in 5th grade, we pretty much knew what we wanted to do
with girls, and certainly what we wanted them to do to us. With no real
porn magazines or internet available, all we could do is rely on our
imaginations to guide us. One evening when we were camping out in the
backyard, we were talking about a girl that lived about 3 houses down the
road from us and what we'd like to do to her or have done to us. We were
jerking each other off and the subject turned to blow jobs and how we both
thought that we'd like for her to show up and suck both of us. Well of
course that wasn't going to happen, so my friend asks "I'd really like a
blow job, if you give me one, I'll give you one...no one will ever know."
Hmmm, another turning point in my life was about to happen. I said, "Ok if
you go first, because I don't trust you" He thought about it for a minute,
and we made a pact never to tell anyone about what was about to happen. I
pulled open my sleeping bag and my cock sprang straight up in the air. He
slid out of his bag, threw his legs over me and unceremoniously took a
hold of my cock. After a few strokes, he very slightly put his tongue on
the tip. A moment later he put the tip of my cock in his mouth....that was
it, it lasted all of 5 seconds, rolled over to his side of the tent...he
said the thought of him blowing me made him sick and he didn't want to be
a homo...the word for a gay person back then. Damn, that felt pretty darn
good! So he laughs and says, "Ok, time for you to suck me and you to be a
homo." I thought I was going to die, but I had to live up to my part of
the bargain...he was my best friend. He pulled his tighty whities down and
out sprang my next to favorite cock. I slid over on top of him and gave
him a few obligatory strokes. The tip was already glistening with pre-cum
as I hesitantly licked the tip of his dick. Hmmmm, I didn't mind the taste
of that at all! I then slowly put the head of his cock a few inches inside
my mouth. What I remember to this day is the hard, but soft smooth texture
of this favorite piece of meat. It took me a few seconds to get use to it,
but I gently started to move up and down on it the way we had read about.
He was writhing and moaning up a storm, so much so I had to stop and tell
him to be quiet as we didn't want to wake up the parents. After a moment
or so, he got the hint and shut up so I could resume the blow job. I
softly continued, thinking this isn't so bad, I hope he gets to like
blowing me as well. It could replace those jerk off sessions. Thinking
along those lines and getting more action, he was thrusting pretty hard
into the back of my throat. I could feel a familiar throbbing starting in
the shaft of his cock. Oh no, I couldn't let him cum in my mouth! I pulled
it out to the edge of my lips and was thinking what to do when the first
spurt hit me on the lips! Wow, what a surprise. I quickly moved my head
back a continued stroking him until he finished. What a load!
Unconsciously, I licked my lips and got the first real taste of cum...yes, I
thought that this isn't bad at all. My buddy admitted it was the best cum
he ever had and he wanted me to give him more. Well as it goes, he tried
to blow me a couple more times and it didn't work at all for him,
therefore he never got another blowjob from me.
So much for growing up...as I said it was the 60's. I was about 5'10",
scrawny with longer than a Beatles haircut. I probably would have let it
grow longer, but I had a good job and my boss wouldn't appreciate it. He
almost flipped out when I had one ear pierced. I was also on summer break
from a northeastern college.
My new girlfriend's name was Carla. I'd met her one night out dancing and
having a few beers. It turns out we both had the same type sports car so
we had something in common. After a couple of dates, we found out what we
both really had in common...we loved to suck and fuck each other! I knew she
had another boyfriend, but he was away at summer school. It seems he
enjoyed the party life at college too much and to stay in, he had to make
up some classes. After all, there was the draft back then and nobody
wanted to flunk out and lose their deferment.
One evening after going out and dancing, we got back to Carla's apartment
to enjoy each other's bodies. After a great session of licking and
penetration we were laying back enjoying each others company when I
remarked about the cute pair of bikini panties she was wearing. She said,
they were new and a lot cuter than guys underwear... I want to try them on
you if that's ok? I could feel those old desires coming back, and said
sure, whatever floats your boat. She tossed them in my face, a nice new
pair of nylon and lace, flowery and sweetly smelling of her pussy. So,
what's a guy to do but pull them up my legs and feel that wonderful
feeling of nylon encasing my cock again. Wow, I was immediately so hard
that she commented on how I seemed to enjoy wearing them...I said, "you bet
I do, these are pretty stimulating knowing they were just covering your
sweet pussy, but they are also quite comfortable, a lot more comfortable
than those cotton things with seams irritating you dick" Carla then
surprised me by gently stroking the front of the panties, oh man that felt
so good...My cock was now sticking out the top of the waistband...she was
still stroking and gave me a little kiss on the tip. Well, don't stop now,
I had just finished a good fuck session but was ready for this blow job
that only took about 15 seconds. Wow, she said, I guess those do make you
horny, maybe you should have a few pairs of your own if they are that
comfy and make you that horny..well, I thought, that works for me!
The next day I went home and thought to myself that I should go and get a
few pairs of panties or bikinis. The only stores that carried bikinis were
the better department stores, all the others sold boring solid white or
pink cotton panties. Terrified as I was, I chose one, maybe it was G.Fox,
went inside and bought 2 pairs of black cotton bikinis and 2 pairs of
nylon, one in black and one in bright red! I hurried out of the store,
drove home and one by one tried them on. Ah, the cotton ones were comfy as
I thought, I can get away wearing these day to day. The nylon ones were
naughty and immediately I was hard trying them on. I knew I'd wear them on
my next date with Carla, but which color? Black is the easiest to get away
with thinking it's pretty easy to justify the color, but red is a pretty
good indicator that I liked them better than I had let on...ok, red it was!
Carla worked in one of the big insurance companies in the city, had a good
job and made a decent living. She was a girl with goals, so she took on
the Mary Kay line of cosmetics just when Mary Kay was getting started. On
our next date she said that she wanted to give me a facial as she needed
the practice for her Mary Kay work. So after dinner and a few too many
drinks, we went back to her place to "practice". She had me take off my
shirt and sit in a chair with a smock so she could work on me. Rubbing and
messaging my face with all the various creams was really nice. She then
decided to sit in my lap facing me, kissing me now and then and apply more
cream. Well, this had the nice affect of giving me a pretty good erection
which didn't go unnoticed. Carla got up and unzipped my shorts and felt
inside for my cock...a funny look came on her face when she felt the nylon
bikinis. She got up, had me stand and drop my shorts, that's when the red
bikinis had the desired effect. Carla's face lit up and she said what a
naughty boy I was to wear red bikinis on a date. She started the old trick
of stroking me and of course in 10 seconds I was poking out the top of the
panties. She then pulled up her skirt, dropped her panties and slid that
beautiful, warm, juicy pussy over my cock which was still in the panties.
Oh my, we fucked our brains out, but the nylon on my dick made me cum way
too fast. She hopped off, wiped my face clean and dragged me upstairs into
her bedroom. She then dropped the panties and mounted me, this time taking
long enough for her to have an enormous orgasm. Carla asked about how I
got the panties and I told her the story. I fibbed a bit when I told her
that they were just a lot more comfortable that guys underwear. She said,
"Oh yeah, and that's why you chose red nylon ones, comfy and sexy!"
We continued dating throughout the summer. Most all of our dates ended
with some kind of sexual experience. Her Mary Kay appointments grew, so
being mostly in the evening, we didn't see each other as early, but had
fun later. Mary Kay had introduced new lines of makeup and cosmetics and
Carla need a person to work on. I'd go over to her house and every night
and she told me that if she could make me look good as a young girl, she
could make anyone look good...well Thanks! Some nights she would apply
different foundations, wipe them off and try another shade. Other nights
it would be eye liner, try and go for different looks by drawing the liner
around my eyes differently. Next was the eye shadow, there was a lot of
colors, so she would do one eye in one shade and another shade on the
other eye, that looked pretty funny and we both had a good laugh over it.
Lipsticks were another several nights, my lips got sore from all the
wiping and cleaning and yet another shade...oh, what's a guy to do to get
laid. Most often Carla would wind up the makeup session by dropping my
drawers and remarking about my new bikinis and giving me a wonderful blow
job. This eventually worked into a lovely fuck that we both enjoyed. My
panty collection had grown and I was now wearing them 24/7. I really was
getting attached to Carla but knew she still had feelings for her
boyfriend in school. Oh well, things work out for the best and I was
enjoying this a lot!
One Saturday Carla invited me over early in the day as she had some new
products to try out on me and she wanted to be ready to show them early
the following week. I got there about 9 am and we had coffee and went
upstairs to her bedroom where there was a makeup table with more stuff on
that you could imagine. I sat down and she said something about my hair
being kind of messy and could she play around with it a bit? Sure why not,
it was getting a little longer, needed a hair cut but she could play all
she wanted. After about 30 minutes of snipping, combing, rollers, again
combing, then spraying, she said for me to check out her work. Hey, that
looks pretty good, a little feminine, but in those days, who's to notice.
She then started putting on a hot mask product that was to open and
cleanse the pores. This really felt good on my face and everyone should
have this done. Her phone rang and it was Carla's boyfriend from college,
he had come home early and wanted to come right over. Oops, he only lived
15 minutes away and I would never get out of there in that time. She had
an idea, keep on the mask, pull on one of her tops and wear a pair of her
tight jeans with flip flops. She said if I could pull it off, it would
save her ass big time. So, if I didn't have anything to say to anyone I
probably could get away with it. She had me put on one of her bras, a bit
of pantyhose stuffing, a light colored stretchy top with puff sleeves, and
a pair of size 9 jeans...wow were those tight! She put the hairdressers
smock back on me and fluffed my hair just as the doorbell rang. Tom was
there and he'd brought a friend of his named Jeff from college for the
weekend. I could hear Carla downstairs talking to them and everything was
cool until Tom mentioned the other car in here driveway. She said that is
my girlfriend Dee upstairs, we were testing out some new masks. Dee, well,
that was quick thinking, I wonder how long she'd had that name made up for
me. They were still chatting and having a beer when Tom's friend Jeff
said, ask her down here for a beer I'd like to meet her. Oh shit, here we
go, someone's gonna get their ass kicked about this, and it'll probably be
me. Carla say's "hey Dee, get your butt down here sweetie and have a beer
with us. Don't wipe the mask off yet it still needs to be on another ?
hour before we can remove it. Don't worry, no one will laugh at you" Oh
double shit, here I go...I get downstairs and get introduced to Tom and
Jeff, both good looking guys. Carla says, "don't talk, I don't want you to
mess up that coverage, just nod yes or no...do you want a beer with us?"
Thank goodness she just saved my ass...I nod yes and put up 2 fingers
meaning 2 beers, they all laugh. So far so good....I drink them fast enough
to take away the jitters. Half hour later I think things are winding up as
the boys have to go to a ball game. As they are leaving Tom asks Carla
what time she can be ready tonight as he plans on taking her to the drive-
in movies. Jeff chimes in and asks me if I'd like to go with him...I shake
my head no...he says I have to as he wants to really see what I look like
under all that mud...dumber than I Thought. I still shake my head no, but
Carla says of course she'll go, I'll talk her into it. It gets dark about
9, so we should get there about 8:30, pick us up at 8. As they are leaving
she says, you boys bring the beer or Ripple.
So, I get her alone and ask just what she was thinking? She of course
doesn't want to mess up with Tom and she thinks it'll be fun to have me
along as her girlfriend. Hey' she says, I know how beautiful I can make
you look, Jeff will never know you're a guy, just go along with the
program. What maked me agree I don't know...maybe the new panties were too
tight. Carla takes the mask off and my face feels wonderful. She remarks
what a nice glow that I have and we should do this more often, I kind of
agree. It's now about 4pm and we need to eat something, so off to store we
go. Carla says to stop at the Kmart as they have a special on piercing and
earrings. We go in and she picks out a couple of cute sets of earrings and
speaks to the salesgirl. The gal says to sit down and in less than a
minute my other ear is pierced and a set of studs is put in. Carla goes
through pantyhose section and picks out 2 pairs, one for her and one for
me. Then it's off to the shoe section where she picks out a pair of pumps
with one inch heels, size 10, easy for me to walk in. The bra I had on
earlier was pretty tight so she picks one size bigger than hers, size 36C.
Oh goody, big boobies, just what I need for a first date with a guy I
don't even know. This all goes to prove the power of the pussy over us
guys.
We grab a bite at the local burger joint and head to Carla's for the
makeover. First she has me take a shower..but first rub myself all over
with a bottle of Nair....shower off, lose that hair. She has me pull on a
clean pair of her bikini panties, followed by a suntan pair of pantyhose.
By now, I'm getting kind of hard and it's showing. Next, a light blue bra
stuffed with more pantyhose...ok, so now I've got a raging hard on. Carl
looks at me and says we can't have that happening so down comes the
pantyhose and panties and I get a wonderful blow job that lasts about 30
seconds as I'm so horny. Up go the panties and hose and out comes a very
restrictive garment called a girdle. As she has me pull that on, I can see
it will never ever show my cock through it. As she pulls out a black mini
skirt I remark, "holy shit, I can't wear something that short" She thinks
a minute and says I'm right...out comes a pair of decent cotton shorts that
fit like a glove. Next goes on a flowery, white cotton top that leaves
nothing to be imagined in the breast department. She sits me down and
starts on the makeup. By now Carla knows what to use on me and it goes
pretty fast. She paints my nails a light pink and I wait for them to dry
thinking, nice color! She takes out a curling iron, curls my hair a little
and fluffs it up. The she puts in the big hoop earrings I thought she
bought for herself, but were really for me. She then has me put on the
heels and walk over to the full length mirror. Needless to say, her
practice on me made me look every bit a 21 year old girl, or girlfriend as
she would say. "Dee, you look very cute, no guy will ever know you're a
not a girl unless you take out your cock..and I'm sure that's not going to
happen with that girdle on I gave you..Ha!" Walk around a little and
practice, I also want to hear you practice your voice. You shouldn't sound
like a guy nor should it be to high and squeaky. I practice and Carla gets
ready in no time at all, the doorbell rings, it's the guys.
Moment of truth, Carl says for me to open the door for them and let them
in as she has to put on her top and finish her hair. My knees are shaking
as bad as anything, I can barely walk in these heels and I'm afraid of
what my voice will really sound like. I open the door and say come on in
boys, the are beers in the fridge. They walk in and both of them are in
awe of how I, Dee, look as compared to the other day. I look so good I
don't think they care what I sound like, especially Jeff as he is my date
and was worried as hell after seeing a muddy faced girl that morning. Tom
get us beers and were enjoying them when Carla walks down and make her
entrance. She gets a beer and hands me a small purse for me to keep the
"essentials". A little chit chat about the game, another beer and we
climb in the car to go to the drive-in.
Tom and Carla are in front and Jeff and I are in the back set (of course!)
What really surprises me is that it's a station wagon and has a huge back
complete with sleeping bag and pillow...what a lucky girl I am. Of course we
park in the back row where all the make out artists take their girls. We
break open the wine and after a couple of glasses I'm feeling kind of good
about this girl thing. Who knows what the movie was as Tom and Carla
disappear down in the front seat. Lover boy Jeff is all over me and
finally kisses me very gently on the cheek and then the lips. Hmm, not
bad, it's better that fighting him all night. Next move is better, a
little tongue, a nice deep French kiss which I kinda like. This guy has
nice lips, just as soft as most girls I dated. Another glass of wine and
he has his tongue in my ear..holy shit, now I'm getting horny. The girdle
is holding back a pretty good hard on and it better not sneak out.
Another few kisses and tongues in the ear and I've got to get out of there
and pee.
I call for Carla to sit up but realize she's in the middle of a blow job.
What, my girlfriend giving another guy a blow job?? I'm really jealous,
but wait a few minutes and announce, "Carla, I've got to pee and you need
to go with me." She sits up licking her lips...I've seen that look before,
and says "Ok don't get your panties in a bunch, wait a minute." She wipes
her face with a tissue, I grab my purse and we get out to go to the ladies
room. This is going to be a new experience, as she warns me to sit down a
pee. After I peel off the girdle, the pantyhose and then the panties, I
can pee. It seems like it takes forever, and I hope I don't have to go
through this again. After I get everything put back in the proper places,
I meet Carl waiting for me in front of the mirror. She says for me clean
up my face and get the lipstick out of my purse. As I'm digging through it
I find there are 2 condoms in there as well. I know they aren't for Carla
and I as she is on the pill and I don't wear them fucking her.(pre-HIV).
She just laughs and says a girl has to be ready for anything you
know..ready for what I can only imagine. I apply the lipstick and mention
that Jeff is pretty horny and he's all over me. Carla laughs and asks
what I'm going to do about it, I say that if it was me, if I had a good
cum, it would probably settle me down. She says, again, what are you going
to do about it? I said I thought I may give Jeff a hand job and he'd
settle down and leave me alone. Carla says, don't you dare give him a hand
job in the car, it get all over my good clothes I lent you and probably
all over the car too...she had a point. I ask, but already know where this
conversation is ending. I say ok, I'll control the situation, but he had
better not stick his tongue in my ear again, that isn't fair!
We get back in the car and I kick off my heels and get relaxed with
another glass of Ripple. I snuggle up to Jeff who is gently rubbing my
thighs and trying get my hand on the front of his pants. I'm pushing away
pretty successfully except the rubbing my nylon covered legs is getting me
horny again. The Jeff starts kissing me and sticking his tongue in my ear,
plus he's rubbing my legs....Ohhhh, I'm going to cum in my panties if he
doesn't stop. OK, Dee, control the situation, I make a slight move and put
my hand on the front of his pants. This makes him stop...for about 10
seconds, then Jeff re-doubles his efforts. I rub a little more and now
I've got his attention as he pulls down his pants and pulls out a very
nicely shaped cock. Hmmm, what to do, I gently give it a few strokes with
my hand when I hear Carla in the front seat going "Ahem"...ok,ok...I stop for
a second and my mind jumps back to my best buddy and I camping. Hey, it
wasn't so bad back then, and Jeff's a nice guy that doesn't need messy
pants or blue balls from his date. I scoot down in the seat and take a
look of this life changing cock in front of me. I can see the pre-cum
glistening in the light of the movie. So, what's a gal to do but take this
cock in her mouth and give it a little suck. In fact a nice big sucking
pop, that gives Carla the idea of what's happening. I hear a chuckle from
the front and continue on with my licking and sucking. Jeff's enjoying
himself, I'm thinking this is kind of fun, he's nice and clean, and is
even starting to grab the back of my head as he wants his meat deeper in
my mouth. Now, I had heard of deep throating, but that was just a concept
in those days. However, after a few gags, I got use to it, and enjoyed
having that nice cock in my throat. Just when I was happily fucking his
cock with my throat I felt that stiffening, that throbbing start and all
of a sudden Jeff was pouring 2 hours of stimulation down the back of my
throat. That surprised me, but I kept thinking of Carla. I should keep
Jeff's clothing and her clothing clean by swallowing almost every drop.
When I got up, I noticed Carla looking back and saying quietly "way to go
girl" I chuckled as she pointed to her chin meaning I had a nice glob of
cum that need to be cleaned off. I looked at Jeff who was pulling up his
pants and he gently kissed me...wow, a kiss after a blow job, this guy is
really swell. I put on some new lipstick, snuggled back into his arms and
we headed to our respective homes, Jeff was going home with Tom and I was
staying with my girlfriend Carla.
Carla couldn't wait until she could get me in the door and quiz me as to
what happened with Jeff in detail, and I mean everything.
Next: Sunday's date.
Like it? What should Carla and Dee do on their double date?
[email protected]
Kaylin
- 12.05.2021
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