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My first Time With My Best Friend 
by Barrack David (iw57@jove.acs.unt.edu)
1996

***

I wrote it from the female's point of view, so I would 
really appreciate any female feedback I can get. The 
story is about a girl having her first bisexual 
experience with her best friend. (FF, MF, 1st-bi-expr)

***

Jackie and I were sitting on the couch, watching some 
cheesy USA up all night movie, when it happened. We had 
both just finished with our men, who were in our rooms, 
sleeping. If there's any one thing that annoys me about 
men, it's their tendency to use up all their energy on 
the first go. 

Cyrus (that's my man... everyone calls him Cid) is 
usually pretty good about that, leaving himself some 
energy in reserve, but tonight he was like a wild 
animal, which, mind you, I enjoyed... but sex itself 
turns me on, so I usually like to do it more than once 
in a row. 

I suppose I can't blame him though, we hadn't been 
together for two weeks. We usually get together on the 
weekends, but our obligations kept us apart. I had a 
paper to write, he had a track meet to go to, then I 
had a test to study for. He was really aching for it 
tonight, so I decided to play hard to get, which didn't 
last very long. I dodged around the room until he 
grabbed me and threw me down on the bed. I might have 
kept struggling, but I wanted it too. I let him hastily 
pull off my clothes while I listened to Jackie and 
Orlando in her room. 

Jacosta is kind of a shy girl, but I could never think 
of her as innocent... she has the loudest orgasms I've 
ever heard. When she's in the shower, by herself, even 
when she knows I'm in the apartment, she still makes 
the biggest commotion. I have to admit, it kind of 
turns me on. I guess hearing anyone having that much 
fun is kind of exciting, though. Not that I'm trying to 
make up excuses, but I've always been afraid that I 
might be a little bisexual, and couldn't ever really 
admit it to myself. 

The thought of being intimate with another woman never 
actually turned me off, but I've never told anyone 
that. I have been thinking about it recently though, 
mostly because of Cid. He tells me that it's my only 
shortcoming as a lover, that I'm not bi. I was kind of 
surprised to hear it, but I guess it makes sense. All 
the pornos I've watched have lots of bi and lesbian 
women in them, so I guess it really does turn them on. 
(Guys, I mean.) 

Cid got me down to my little lace and silk panties when 
he had to stop and take off his own pants, complaining 
that his 'Womanpleaser' as he likes to call it was 
getting to big for his britches. You might think that 
the name Womanpleaser is a bit arrogant, but then 
again, I've never had any complaints about his 
performance. 

He finished getting naked, down to his socks, and 
pulled off the last of my underwear. Actually, it was 
technically his underwear, because I gave it to him 
last Christmas. I showed up to the Christmas bash 
wearing a ribbon choker with a bow on it. After all the 
other presents had been opened and everyone else left, 
I let him unwrap me. That was the first time we did it. 
It was also the first time I had worn sexy underwear. 
I've been doing it ever since, not just to please him, 
but because it makes me feel sexy. 

Well, any ways, there we were, naked on the bed, and 
I'll spare you the gory details, but I will tell you 
that he was not gentle, which I got off on immensely. 
Unfortunately, like I've already established, he 
basically came and went. As soon as he was finished, he 
rolled off of me and fell asleep so fast that I barely 
had time to compliment him. 

The up all night movie wasn't exactly holding our 
attention, so me and Jackie began to discuss this 
shortcoming in men. According to Jackie, Orlando was 
consistently guilty of this, but it was most likely 
because he insisted on doing all the work. At some 
point in the conversation, I noticed that my roommate 
had draped her arm around my shoulder. 

I looked at her hand, and then back to her. "Cold?" I 
asked, completely innocently. She nodded and slid a 
little closer to me. She was only wearing an oversized 
T-shirt and some socks. I had on my big flannel night 
shirt and Cid's boxers, and I was plenty warm. I put my 
arm around her and she put her head on my shoulder. 

I don't mind being familiar with Jackie, mostly because 
neither of us are bi, and I know nothing would ever 
happen between us. 

Boy, was I wrong. 

She did it very slowly, snuggling closer and closer, 
putting her hand on my lap, moving her head closer to 
mine. Thinking back on it all, I don't think that I was 
aware of these little movements of hers, even if I was, 
I didn't think anything of them. When the commercial 
came on, I turned to her to tell her that I was going 
to get her a drink. As soon as I opened my mouth, she 
pressed her lips against mine. 

I froze solid. I absolutely could not think of anything 
to do. I just sat there, eyes wide. Her eyes were wide 
too, staring back into mine. I felt her body trembling. 
I think it was her. It was probably both of us. Jackie 
started to slide her hand up under my shirt. I was 
going to stop her, but she slowly pulled her mouth 
away. 

"Why are you doing this?" I whispered, in lieu of doing 
anything. 

"I... don't know." She said in a faltering voice. Her 
hand touched my breast. We both jumped a little, I let 
out a nervous whimper, and her eyes widened slightly. 

"Why aren't you stopping me?" She shuddered out. Her 
hand gingerly kneaded my breast during the moment of 
silence that followed. 

"I..." More silence. 

"I... don't know." She moved her mouth back to mine. 
Again, I was unable to move. She pressed her lips to 
me, gently at first, then more fiercely. This time, she 
slowly started to slide her tongue into my mouth, which 
caused me to slide away from her. 

"No, please..." I fell back onto the couch, and Jackie 
quickly crawled on top of me. She laid on top of me 
kissing me again, with even more tongue. I tried to 
push her away, but my arms were trembling so badly, 
they had no strength. Under normal conditions, I am 
considerably stronger than her. She is eight inches 
shorter than me, and she doesn't work out nearly as 
often. 

Under these conditions, I could barely support myself. 
I gave up, laying there numbly while she kissed my 
mouth and face. She slowly started to unbuttoned my 
night shirt with trembling hands. She fumbled the 
buttons so badly that she could only do two herself. 
She put her hands on the couch next to me and looked 
into my eyes. 

"Help me." She pleaded, voice trembling so badly that 
it almost sounded like she was crying. 

I stared up at her for a moment, then slowly moved my 
hands up to the buttons. I don't know why I did it. I 
don't know why I did anything that night. It might have 
been the nervous, pleading look on her face. It might 
have been the fact that I had secretly fantasized about 
this once or twice. It might have been the fact that 
Cid had repeatedly told me that bisexuals turn him on. 

It might have been sheer curiosity. Whatever it was, I 
finished unbuttoning my shirt while Jackie resumed 
nervously kissing me. I closed my eyes, and the 
sensations became familiar. Except for the smell of her 
hair, and the small noises that she made, it felt the 
same as being with a man. 

Her mouth found it's way back to mine. She licked my 
lips, then the edge of my teeth, then my tongue. I 
returned the gesture, sliding my tongue into her mouth. 
I felt her body stiffen for a moment, then relax more 
than it had been before. She scooped up my head and 
kissed me passionately. I surprised us both by running 
my hands through her hair, and pulling her head more 
tightly to mine. We kissed passionately for several 
moments, a thousand things running through my head. She 
pulled slightly away, lips still touching mine. 

"I can't believe this is happening." She whispered, her 
breath hot in my mouth. 

I looked at her incredulously. "You're the one who 
started this." I brushed her platinum blonde bangs out 
of her face, waiting for her response. She stared at me 
for a second, then buried her face in the small of my 
neck, laughing. 

"Shhhhh, shut up, we don't want the guys..." Something 
occurred to me at that moment. "uh, finding us like 
this, do we?" 

"Uh, no. I guess not." 

"Jackie," I cut in. "This might be a bad time to ask, 
but you didn't, um, did you get oral with Orlando?" 

"Um, no, why?" 

"Because you've just had your tongue in my..." 

Jackie's eyes widened with realization. "No!" She burst 
out in a suppressed giggling. "You didn't... you know, 
with Cid?" 

"No." We both laughed quietly for a while before we 
started to feel uncomfortable again. The giggling died 
away, and we were left with silence. We stared at each 
other for a while, until Jackie leaned in for another 
kiss. The nervousness immediately returned, but I let 
her kiss me anyway. I closed my eyes again while she 
continued kissing me, and I relaxed slightly. 

She started kissing me on the cheek, then the jaw, and 
down my neck. I knew where she was going, and I grew 
tense again. Her lips moved down my chest, until they 
reached my cleavage. I began to shiver slightly. I'm 
not sure why really. It didn't tickle, or give me the 
willies. I guess maybe it was just happening too fast. 

I felt her soft lips on my skin, playing around in 
between my breasts. She slowly started kissing her way 
up the crest of one of them, and I felt her start to 
shiver to. When her tongue reached the nipple, my 
shivering became an uncontrollable trembling. 

"What's wrong?" She asked. 

"You mean besides the fact that my best friend has her 
tongue down my shirt?" I smiled weakly. 

"Do you want me to stop?" She asked quietly. 

"Um..." I tried to think of a way to say yes without 
actually saying it. "Um..." 

Jackie knew what I wanted to say, so she pulled me up 
on the couch before I could say it. She straddled me 
and took a deep breath, preparing her argument. 

"Kory I... consider you to be my best friend... and, I 
mean, I can talk with you about things that I don't 
think I could ever tell Orlando... you know, other 
guys, and sex, menstruating, my fantasies, you know... 
girl talk." 

I nodded slightly, glad to let her do all the talking. 

"Well, there are some of my fantasies that I haven't 
told you about..." She swallowed. "But I guess I don't 
have to now..." She laughed nervously. My silence was 
uncomfortable, so I laughed too. 

 "I mean," she continued, "if I can do all that with 
you, why can't I do... other things?" 

"Because... it's gross?" 

"Gross..." She looked for the right words. "...is 
learned, and it can be unlearned, right?" 

I didn't want to answer her, because I knew she was 
right, but I couldn't say nothing. "Well... I... 
guess." 

She cupped my head in her hands and looked me in the 
eyes. 
"Kory... will you... un-learn gross with me?" 

My throat tightened slightly. It was a yes or no 
question, but it wasn't that simple. While I agonized 
for the nicest way to say no, Jackie slowly leaned in 
for another kiss. I tried to turn away, but her lips 
found mine anyway. 

There was no tension in my body. I was still a little 
uncomfortable with it, but even with my eyes open, it 
felt only slightly odd. It seemed her little confession 
to me had softened my resolve somewhat. My mind raced 
for something to say: I wasn't going to say yes, but 
something, somewhere in the back of my mind didn't want 
to say no. I guess it was that little part of me that I 
was always afraid of. I felt Jackie begin to knead my 
breasts, so gently that it didn't seem obtrusive. 

I started to think about Cid, and his constant jokes 
about how I should become bi, so he could watch me and 
my girlfriend get nasty together, and, of course, join 
us. And I thought of my fantasies, getting drunk at a 
party and waking up the next morning in bed with 
another woman, or waking up to find that Jackie had 
snuck into my room and tied me down and gagged me so 
she could have her way with me. 

"Jackie?" She stopped. "Tell me about your fantasies." 

She looked at me for a moment, then settled down on my 
lap. "Ho boy, um, well, I've fantasized about being 
woken up by you climbing into my bed..." She stopped 
for a moment, not sure if she wanted to confess her 
devious little fantasies to me. "...and, um you 
basically do to me what I'm doing to you." 

"What," I interrupted. "Um, made you do this?" 

"Um, I guess I got tired of waiting and hoping that you 
eventually would, um, you know, make the first move." I 
watched her closely as she fidgeted slightly. "Plus 
Orlando didn't, you know..." I stared at her. "He 
didn't, you know, completely satisfy me." I smiled 
slightly, knowing exactly what she meant. "I mean, he 
did, but just not... enough." 

I smiled. "Yeah, I know what you mean. So you decided 
to seek satisfaction elsewhere?" 

"Well it's not just that, I mean, I've kind of always 
wanted to be... intimate with you." Her voice faltered 
slightly. I guess it was easier to do it than it was to 
articulate it. "Not just sexual either, just... 
cuddly." 

We looked at each other for a long time while we 
thought our little thoughts, wondering what the other 
one was thinking, and what would happen next. 

After a few more moments of uncomfortable silence, 
Jackie finally spoke. "You're not... mad at me, for 
doing this, are you?" 

I tried to think of something sarcastic to say, but I 
couldn't, so I spoke honestly. "No... mad isn't the 
right word, more like, um, well I guess shocked. I 
never seriously imagined myself doing this... but no, 
I'm not mad at you." She smiled shyly, stroking my dark 
hair. 

"Besides, I've... had fantasies, um, about this too." 

Jackie stared at me, her expression a mixture of 
surprise and knowing. I thought of all the things that 
she had said, about being intimate, about hugging and 
cuddling, being with me to compensate for Orlando's 
lack of endurance. She quietly played with my body 
while I thought, gently kissing and kneading, evidently 
out of things to say. 

I tried to think of the advantages to accepting 
Jackie's offer. As a woman, Jackie would know all the 
right places to touch, would probably want to do it 
more than once in a row, and would be more sensitive to 
my needs as a woman. I lost my train of thought for a 
second, realizing just how casually I was thinking 
about things that would have given me the willies just 
twenty minutes ago. I also realized the fact that my 
roommate was sitting on my lap, kissing me and fondling 
my breasts, and it didn't bother me hardly at all. 

"Jackie." I took her playful hands in mine. She stopped 
and looked into my eyes. "I will... un-learn gross with 
you." I couldn't believe I had said it. I stared at 
Jackie for a tense moment, until she collapsed against 
me, sobbing quietly on my shoulder. It was far from the 
reaction that I had expected. I thought that she'd give 
me a long deep kiss or something, but not this. 
"Jackie? Are you ok?" I stroked her hair, not really 
knowing what else to do. 

"Yes." She sniffed and took her head off my shoulder. 
"Yeah, I'm ok. It's just that..." 

"What?" 

"It's just that, working up the nerve to actually... do 
this." 
She was trembling slightly. "It's the hardest thing 
I've ever done." She went to wipe a tear from her 
cheek. I stopped her and did it myself. She looked into 
my eyes, and slowly leaned in for a kiss. I met her 
halfway and kissed her passionately. It was strange, 
now that I had committed to doing it, it didn't feel 
awkward at all, in fact, it was strangely arousing. 

Apparently Jackie thought so to, and returned my kisses 
fiercely. She moved her hands back to my breasts, 
kneading them and paying expert attention to the 
nipples. I slid my hand under her shirt, reaching for 
her breasts. She inhaled sharply when my hands reached 
them, increasing the fierceness of her kisses. We were 
quickly caught up in an escalating whirlwind of 
passion, not just from the physical stimulation, but 
mostly from the fact that we were 'breaking the rules' 
as given to us by society, as well as living out a 
fantasy or two. 

 As exciting as I found it, Jackie was still a little 
more exploratory than I was. She hooked a finger into 
Cid's boxer shorts and pulled them open slightly. I 
stopped kissing her and stared her in the eye. She 
looked at me questioningly, her hand hovering above my 
stomach. I wasn't sure if I was ready to go so far so 
fast, but I nodded, with just enough reservation on my 
face to let her know to go slowly. My breathing 
quickened as she slid her hand down my abdomen. She 
stopped just short and widened her eyes slightly. 

"You shave?" She giggled. 

I laughed nervously. "Um, yeah. Actually, I nair." 

"Did you do it for Cid?" She started sliding her hand 
down further. 

"Yeah, he says it totally turns him on. You know, most 
porno stars shave, and..." I stopped mid sentence as 
her fingers felt in between my legs. Two sensations hit 
me at the same time. One was a cold chill, the kind you 
get when something really scares you. The other was the 
sort of shiver that I have a tendency to get when I'm 
in an elevator and it drops suddenly. 

As far her touch, well, let me just say that it was 
obvious that she had had some practice at this. Little 
muscles in my body started to contract involuntarily as 
her fingers moved around in my soft folds. I felt the 
pleasure building, but I found that I couldn't look 
Jackie in the eye while she was doing it. 

I grabbed her hand. "I'm sorry, Jackie... It's too 
fast." She nodded and withdrew her hand. "Maybe next 
time?" I suggested. 

She smiled. "So there will be a next time?" 

I looked at her shyly. "Yes. Definitely." 

She gave me a long deep kiss while we fondled each 
other. 
"Kory, I'd like to stay and cuddle, but..." 

"You're too aroused?" I said, pinching her hard little 
nipples. 

"Yeah, I'd guess that you are too?" She returned the 
pinch. 

I nodded. "I'm gonna go kick my man outta bed and make 
him earn my affections." 

She smiled. "Me too." 

We kissed one last time before moving back our rooms. 
Jackie gave me a slap on the butt as I turned into my 
room. I went to retaliate, but she put her hand over my 
mouth and whispered into my ear, "Next time, you get to 
be the man." She gave me a wet willie with her tongue 
and dove into her room before I could get to her. 

I walked into my room with my pinky in my ear, trying 
to squish out the moisture, thinking of some way to get 
her back. Cid was asleep on my bed, so I very carefully 
eased my way in next to him. I started to call his 
name, but decided instead to wake him in a way that I 
had always wanted to. I slid my hand down his lean 
stomach and gently grabbed his 'womanpleaser' and 
slowly began massaging it. He stirred slightly in his 
sleep. 

Obviously his dream had taken a turn for the better. It 
hardened slightly, and I wrapped my mouth around it, 
sucking lightly at first, then harder. Either he was 
going to wake up, or he was going to have one hell of a 
wet dream. He stirred more, tossed his head a bit, then 
snapped his eyes open. 

He sat up in bed, looking at me. "Wh-what?" He blinked, 
trying to figure out whether he was still dreaming or 
not. I moved my mouth from his semi-erection to his 
lips. I pushed him down onto the bed and said, "Service 
me wench." He blinked a few more times before smiling 
broadly. 

"I wish my alarm clock would wake me the same way." We 
both laughed for a little bit, then I got serious. 

"Cid, I have a confession to make." He looked at me for 
a second with a 'what' on his face. "I just... um, 
cheated on you." His expression wasn't quite what I 
expected. I didn't think he'd take me seriously, but 
his expression was something like, anticipation. 

"With Orlando?" 

"No, with... Jackie." He got an incredibly stupid grin 
on his face. 

"Really?" He laughed. "You're serious?" 

I felt him growing erect against my leg. I nodded, 
smiling shyly. He whipped his shorts off of me and 
rolled in between my legs. 

"God DAMNIT that turns me on!" 

I couldn't imagine why, after all, he personally didn't 
get anything out of it, but I didn't complain, 'cause 
he was unbuttoning my shirt and kissing by breasts. He 
started biting my neck, which always turned me on, I 
guess mostly cause it tickled. 

I shuddered, and put my arms around him. I cupped his 
jaw in my hands and pulled him up for a kiss. We gently 
licked each others tongues, but Cid didn't waste any 
time, and I soon felt his fingers in between my legs. I 
felt him spread me open slightly as he guided himself 
inside me. It hurt for a second, and I tried not to let 
it show, but he must have felt me tense up or 
something, because he whispered a sorry in my ear. 

I kissed him once and looked into his eyes. "Don't be." 
I said sternly. We kept our eyes locked, and kissed 
again. He pushed himself the rest of the way into me, 
and I grabbed his butt and held him tightly against me. 
I kept him there for a moment, concentrating on the 
pressure and the pleasure that having him inside me 
generated. It was a little ritual of mine that Cid put 
up with for the most part, and he passed the time 
kissing me and biting my neck. He knew I was done when 
I moved my hands from his butt to his chest and gave 
him a little push. He smiled and responded by starting 
a rhythmic thrusting, slowly at first, but he quickly 
picked up the pace. 

We enjoyed each other for a while, and then we began 
hearing Jackie's loud squealing from the other room. We 
looked at each other and snickered. 

"I wonder what he does to her to make her react like 
that?" I murmured breathlessly. 

"Yeah, I wish I knew," he replied. 

"Oh? Why's that?" I stroked his chest as he shifted 
slightly on top of me. 

"Well," he said, with a coy smile on his face, "I'd 
like it if my partner reacted like that..." 

I smiled at him understandingly, then closed my eyes 
and started to really concentrate on the pleasure in 
between us. I rolled my head back on the pillow and 
tried to vocalize it. I started by breathing especially 
heavy and letting a few "Oh's" and "Yeah's" escape my 
lips. I felt Cid's lips on mine, then his breath in my 
ear. 

"God I love you... do it louder." 

I complied, and threw a few "God's" and "Baby's" in. I 
arched my back and raked his chest, and even though I 
used my fingernails, he seemed to really dig it, so I 
let myself go wild. I squealed and spasmed, and 
generally flopped around a lot. I heard him laughing 
slightly at my overacting, but I could tell by the 
strain in his voice that he was going to come soon. I 
grabbed his butt again and pulled him deeply into me. 
He thrust madly for a moment, then put all his weight 
into one last thrust as he came inside me. He pushed 
too hard and it hurt, but in a good way. 

Suddenly my thoughts went back to when I was a little 
girl and I found out for the fist time exactly how sex 
worked. I remember thinking that the idea of the boy 
putting his penis in my vagina was strange and kind of 
yucky, but when I found out that the boy actually 
squirted some gooey stuff inside me, I swore I would 
die a virgin. 

I looked up at Cid as he spasmed his last few drops 
into me and suddenly felt especially affectionate for 
him. I kissed him wetly as he breathed hotly into my 
mouth. 

"That... was fantastic." He gasped. "You should be loud 
more often" He set his weight down on me as he slowed. 

"Don't you dare stop!" I demanded. I was far too 
aroused from all that had happened that night to settle 
for just knowing that I had pleased him. 

"You've got to be kidding!" I was about to get angry 
with him when he continued. "You tell me that you got 
nasty with your best friend and you think I'm going to 
stop?!" He grabbed my legs from behind his back and 
pushed them over my head. "Grab your ankles." He said 
with a large grin on his face. I complied, somewhat 
wide eyed. 

Even though Cid was pretty good at saving up some 
energy for another go, he usually still needed a few 
minutes to rest, but apparently not tonight. He stood 
over me and thrust downward. I squealed for real as he 
bore into me with the vigor of a jack hammer. I came 
very quickly and so hard that I accidentally spit on 
myself. Well, it was a little more like drool with 
propulsion, but the effect was the same. 

 I don't know whether it was the little bit of bi-
sexual news he had just received, or if it was just 
energy recuperated from his nap, but he pleasured me 
three more times that night. After his third orgasm, I 
was sore, (and not just in my muscles), and utterly 
exhausted. He wanted to keep going, but I kicked him 
off of me and rolled over. 

Just as I was falling asleep, I heard him mutter, "Just 
like a woman, no endurance." 

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 49