My Two Girlfriends
My Two Girlfriends
"I can't believe I'm going to be 24 next week and I'm still a virgin!" Huffed Leah as she
slumped back into the sofa. "I've tried getting drunk with the guys, hanging out with them,
everything! Either I just can't get him to make the first move, or I'm just not relaxed enough to
let things get started."
"All that means is that you're not ready yet." Maggie quickly responded.
"When the time is right it will just happen." Said Maggie, not sounding entirely
Now to this point, I have to admit that more of my attention was focused on the game
on TV than the conversation between my girlfriend Maggie and one of her friends. I was aware
of Leah's situation through previous conversations like the one taking place beside me. Not only
was she a virgin in the truest sense of the word, she had never had sex of any kind. No oral, no
fingering, no nothing. The most she had ever done was a little over the clothes rubbing with an
ex-boyfriend, who I imagine exploded with frustration.
Maggie has been my girlfriend for nearly a year, and I first met Leah about a month after
we started dating. When I first learned of the lack of experience of any kind that Leah had I was
in total disbelief.
She is by no means unattractive, standing 5'9", pretty face, short bobbed dark brown
hair, and if anything, too slim at about 105 lbs. The two things that really grabbed my attention
though were her hips and her chest. She has very small hips, barely flaring more than an inch or
two from her waist and small tight butt. Her breasts on the other hand seem entirely out of
proportion with her body. They are a large C/D cup and protrude straight out without a hint of
sag. Her breasts, combined with her small frame and hips make them look even larger, and it's a
near impossibility to not have your eyes drawn to them when talking to her.
Her lack of trust in almost everyone has prevented even the most eager guys from
getting too close. I'm sure that there's thousands of dollars of therapy potential laying in wait for
some mental health professional down the road. Maggie is her one close friend, and by virtue of
my relationship with her, I've been allowed to get pretty close.
We all have a pretty good sense of humour, so as the girls were getting up to go out I
didn't think much of the next comment out of Leah's mouth.
"Maybe I'll just give up the whole looking idea and just be Mike's second girlfriend."
"Sign me up!" I laughed as they went out for the evening, everyone having a giggle at
Leah's last comment. I thought nothing more of it until later on in the week.
Maggie and I were out for dinner one night on the weekend, having a nice time, catching
up on our weeks, when out of the blue she said; "What did you think of Leah's idea?" Having
totally brushed off the statement as merely joking, I needed to be reminded of what her idea
My next assumption was that Maggie was simply trying to tease me to get a reaction and
give me a hard time about 'wanting' her friend instead of her. "I've never even thought about
it." I replied honestly, and then I returned the question "What do you think?"
Thinking that we were going to have a bit of discussion about poor Leah and the
emotional mess blah, blah, blah that we have every time after she comes by, I was floored by
her response. "I think that you should do it for her."
"Huh? You're kidding right?"
"No. I think that you should be her first."
"Who are you, and what have you done with my girlfriend?" Not believing what I was
"Look," Maggie explained to me, "Your first time should be special."
"Yeah, that would be special, me banging your girlfriend, then you killing me. Very
"Mike, Leah's really down about this and it would be good. You're about the closest guy
in her life, and she would feel safe, and you know what you're doing. I know that you'd give her
whatever she wants." She said smiling at me.
"And where would you be?" I asked cautiously and still in shock.
"That's up to her. I don't have any great bi tendencies, but at the same time the
thought of seeing you two together does turn me on a bit."
The no girl-girl action didn't come as a surprise, we had had that conversation a long
time ago. Everything else, well you could have knocked me over with a feather.
"So what do you think?" came the question again
"IÖI don't know." I was in denial of what was happening.
"Well maybe I can convince you." She said with a sly smile and a sparkle in her dark
Maggie is 5'7", shoulder length light brown hair, full lips wonderful curves and the most
spectacular mesmerizing dark brown eyes. She has full perky B breasts with nipples that
protrude like pencil erasers and get hard at the lightest touch, a small waist and hips that come
out and form a perfect ass. She always keeps her pussy perfectly shaved and is unlike any girl
that I've ever been with. She has this killer body, amazing bedroom eyes and has sex like a
stereotypical male. She doesn't really like foreplay, not into oral sex on her, but loves to give
head, likes to fuck and wants it all the time. It's sort of a dream come true, but every now and
then I have to make her take one for the team, because she has the best tasting pussy I've ever
Wrapping her arms around my shoulders she pulled me in for a long passionate kiss,
running her fingers through my hair and down my back. My arms embraced her holding her
head, tracing her shoulders, my hands ran down her sides. As we continued to kiss I could feel
her hands undoing my belt, and the front of my jeans as she slid them down with a push. Her
fingers reaching inside my underwear, grazing my balls as she firmly gripped my cock in her
hand. "Mmmm, it doesn't feel like you need much convincing" she purred, working her hand up
and down on my ever hardening prick.
"I'm not entirely sure" I said, not even believing myself. At this point she could have
asked me nearly anything and I would have readily agreed. Never mind that she wanted me to
fuck her hot virgin friend, with her permission!
"Well I'm not worried, if that was what you're thinking. Leah's never seen a cock before
other than at the male strippers or in magazines, never mind knowing what to do with it. You'll
be good for her. I'm not sure how good she'd be for you. Besides, I know what you like" she
said in a throaty whisper as she slid to her knees, pulling off my underwear as she slid down.
Kneeling there eye to eye with my cock, I had to admit, she really did know what I liked
and loved doing it. Maggie gave wonderful head. By far the best that I had ever had, and when
she was annoyed with me, she liked to remind me that she got that way because of lots of
practice on lots of guys before we met. Regardless, I was reaping the benefits now.
She slowly licked around the head, holding her hand against the base with her fingertips
barely reaching around to touch the top of my balls. Then came the longer licks, like a fleshy
lollypop as she worked her tongue from the base to the tip, never taking any into her mouth,
teasing all the veins with the tip of her tongue making me even harder, if that was possible.
Opening her lips she gradually took the head into her mouth. A groan escaping my lips as she
did so, she rested her lips at the base of the head as her tongue circled around and around the
head of my dick. Easing her mouth open slightly she took even more of me into her mouth, her
tongue working over every bit of new flesh. Slowly at first, and then with more speed she began
bobbing her head up and down on my now throbbing dick, next came her hand, working up my
shaft in an alternating rhythm with her head. As her head came back, her hand comes up,
slowly twisting as she does so. Repeat and increase pace. By now my eyes were rolling back in
my head as she continued to work over my cock, and then suddenly nothing.
Regaining my senses momentarily I see her laying back on the floor, quickly pulling her
visibly moist panties off from under her skirt, revealing her delicious shaved pussy.
"You know what I want" Maggie gasps, as she grabs at my hard prick, shining with her
saliva. Pulling me down and in between her open legs.
I need no further guidance, as I kneel down, pressing my cock between her now soaking
lips, I enter her with a single hard thrust, making both of us gasp with pleasure. I immediately
feel how soaking wet she is and how incredibly hot. Pulling back slightly I relish the look of
pleasure on her face as she opens her legs even wider.
"Oh, you feel so good inside me" she says, as our eyes meet. The encouragement
makes me push even harder and deeper into her, just like she loves. "Mmmm that's it," as more
words of support and affection come from her now gasping lips. Pulling her legs up and placing
them on my shoulders, I push as deep into her as I can go, feeling my cock rub on her g-spot, I
work my hips even faster. The warm wet sounds of our fucking mixing with her moans bring me
even closer to orgasm. After what seems like minutes, and an eternity mixed together, her
gasps become more frantic, and then I begin to feel the contractions of her pussy as she comes
with me sliding deep into her. The pressure of her walls nearly pushes me right out of her as I
begin to come myself. Feeling my load explode deep inside her, I nearly collapse from the
release, as I continue to pump, working out the remains of my climax inside her, she comes to
her senses and kisses me deeply, all the while milking what was left of my orgasm with the walls
of her pussy.
Pulling out, with a muted pop, I roll onto my side as Maggie reaches down to play with
my now shrinking cock. "Now lets go over my plan for you and Leah." She whispers to me, and
deep down my balls begin to stir again.