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Gay stories > Category :
Bisexual > My Threesome with Nancy
By Jay Gannon, 13 Reviews Post your review
Nancy and I had an affair which lasted from 1987 through 1990, although we
continued having sex whenever we happened to see each other for another ten
years. She finally found the man she planned to spend the rest of her life with
and she announced that for once in her life she would give monogamy a try. When I first met Nancy, we were both commuting from homes in Philadelphia to
jobs in New York City. I spotted her one morning on the Metroliner, noted her
dancer’s legs, stylish outfit and stunning face and unleashed one of my best
lines as we stood in line to disembark: “Do you have the time?” Nancy knew what I was up to and treated me kindly. We walked out of Penn
Station chatting and by the time we reached Seventh Avenue, I had her card and a
dinner date. We had a wonderful dinner at Palio, went dancing at a club in the
30’s and spent the evening fucking at her hotel. She was perfect for me. At this point I was 39, married, the father of three.
She was 37, married, childless and unhappy in her marriage. Shortly after we
took up with each other, she got a sublet in Manhattan and I was able to give
mine up and stay with her the nights I stayed in New York, which became many. We
both worked late and would agree on a restaurant where we’d meet for dinner.
After dinner, we might go elsewhere for more drinks, but generally were anxious
to retire to her place for sex. We usually got no farther than just inside the
door before we were in each other’s arms. After kissing passionately for some
time she often dropped to her knees, unzipped me and started sucking on my
already erect penis. In short order, we’d each get naked and feverishly start
fucking. We always had sex twice in the evening. When morning came, Nancy liked to
wake me by burrowing under the covers and taking my cock in her mouth. What was
most thrilling about this was the way she just held it in her mouth at first,
letting it start stiffening in the moist warmth of her mouth. Our morning sex
was passionate, but brief. Wonderfully, Nancy seemed to reach orgasm very
quickly in the morning. After we had both uttered our last moan, we became all
business, preparing to face the day. Nancy would shower quickly, and then turn
the bathroom over to me. While I showered, she placed her daily call to Doug,
her husband. This satisfying routine went on with minor variation for months. One of the
charming things about Nancy was that in the midst of our passion, she would
invariably murmur, “Tell me what you want me to do.” At first I dismissed this
as a simple habit whenever she had a dick in her pussy. Finally, though, I
decided I needed to make a demand. As we rocked in missionary position, I told
her I wanted her finger in my ass. Now she had done this on her own a few times,
but I decided I wanted her to establish it as a regular part of our sex. She
knew enough to put her hand between us and get her finger wet from her juices,
and then she inserted her middle finger deep into my rectum. She was immediately
rewarded as I began thrusting harder, faster and deeper. As hard as I thrust
forward into her vagina, I pushed back into her finger. After a time, she began
inserting her index finger alongside the first. I started making animal noises
as the pressure in my rectum and against my prostate began an ejaculation like
no other I had experienced. My ecstasy triggered hers and we shared explosive
orgasms. That night launched adventures in anal sexuality that I dream about. After we
recovered from our first orgasm, Nancy moved down my body, kissing and licking.
But my penis, which I was sure was her objective, received only a quick suck.
She was focused instead on my anus. She hooked my legs on her shoulders, widened
my crack with her hands and inserted her tongue into my asshole. My reaction was
immediate and wildly enthusiastic: “Yes, yes, yes! Deeper!!! Yes!!!” My depleted
penis stood up in no time. When Nancy felt she me sufficiently aroused, she
straddled me and inserted my penis in her own fully lubricated ass. From then on, I guess I ejaculated in Nancy’s bowels about as often as in her
vagina. For her part, she showed up at dinner one night with a present for both
of us – a strap on cock. She could tell from my immediate and intense
responsiveness to her anal ministrations that I was a man who would enjoy being
fucked in the ass. Indeed, if I never had sex any other way but on my back, my
legs hooked around her as she fucked me with her eight inch black cock, I would
be quite content. As it was, she could clearly understand how much I enjoyed
this aspect of our sexuality. She seemed to enjoy it too, since the pressure of
the base of the penis on her clitoris produced regular and multiple orgasms for
her. Her cock was perpetually hard, and I never asked her to stop. She would
ultimately collapse on me, exhausted from the exertion of thrusting and
enervated by her multiple orgasms. Since we had not only an adulterous relationship, but one that was unusually
intensely sexual, we had no inhibition about discussing our sexual history and
experiences. When the subject of group sex and swinging came up I admitted to
her that beyond discussing swapping wives with a good friend of mine, the
closest I had come to group sex was having sex with my girlfriend in a room with
another couple. They were screwing as well and we watched each other fuck. Not surprising to me were Nancy’s many experiences, with much older men when
she was in her teens, with much younger men currently, and with women of all
ages. It seems that her only group sex took place with two male colleagues with
whom she was taking a business trip some years ago. She had already slept with
each of them, so to avoid the awkwardness of making a choice that evening, she
invited them both to her room. She recounted with great pleasure how much she
got off on kneeling before them, taking one, then the other, and finally both
penises in her mouth at the same time. I asked if her partners seemed uncomfortable having their erect cocks in
contact with each other. She assured me that they seemed to enjoy it so much
that she would make a point of rubbing them together. The highlight of that
night was her first double penetration. Nancy looked at me meaningfully and told
me she wanted to experience that with me. Well, as a man who never turned down a sexual encounter of any type, I was
ready to oblige. I admitted to her that my idea of a threesome was two women and
I, to which she responded that she would enjoy that experience, but that she
called her fantasy first. I conceded the point, and we began discussing
practicalities. Nancy was a very effective person and I had no doubt that she
would have a plan and execute it with energy. What surprised me was that she
already had our third in mind. I imagined that we’d go bar hopping and troll for
a likely looking guy in a suit, the right age, the right look and make his night
by telling him that he had a sure thing in front of him, just so long as he
didn’t mind another guy fucking her at the same time. I thought I’d be gracious
and give him the choice of vagina or anus. Instead, Nancy strongly recommended
we go with a known commodity, known to her that is. Thus I was introduced to
James Carey the very next night at the Zig Zag Bar, down the street from Nancy’s
apartment. Nancy and I were coy about whether we were currently sleeping with other
lovers. I had several women between New York and Philadelphia and I was certain
that she was getting other action as well. As soon as I met James and saw them
relate, I was certain he was more than “an old flame”. He was about my height
and build, grayer and possibly a few years older that I, good looking and
personable. He was a commercial banker and carried himself like a man who knows
how to do relationship business. “Hi Joe”, he greeted me; “Nancy’s told me a lot about you.” I replied that I
was at a disadvantage, and he proceeded to give me a brief life story, telling
me of his wife, kids and dalliance with Nancy. As he told it, his wife uncovered
evidence of his affair, which he denied. He thought it best not to push his
luck, so that currently he and Nancy were simply “close friends”. Of course, I
didn’t believe this for a minute, nor did I much care; I liked the look of the
guy and, to my surprise was increasingly anxious to see the three of us naked
together. He had been thoroughly briefed on the plan for the evening and our
conversation at the bar, lubricated by several rounds of martinis, “to overcome
inhibitions” as Nancy so neatly put it, became ever more sexual. Each of us in
turn recounted an outrageous tale of sexual conquest or kinkiness. I know that I
was getting aroused and judging by the flush on Nancy’s cheeks, she was as well.
Significantly, when it was James’ turn, he talked about being picked up
hitch-hiking by a gay photographer and his seduction. It turns out that
somewhere in the world of porn are a number of photographs of a younger James
sucking on the cock of his patron. That anecdote seemed to signal that the time was right to head down 23rd
Street to Nancy’s. We walked past the bored doorman who undoubtedly knew more of
Nancy’s secrets than I. We were oddly silent on the elevator, each of us
probably wondering exactly how this encounter would play out. Nancy, true to
form, opened the door, stepped in, turned on the light and dramatically leaned
against the entry wall, inviting us to begin making love to her. This is just as
she did it with the two of us. What would happen now? James didn’t hesitate, which further convinced me that he was one of Nancy’s
current lovers. They embraced and began kissing passionately. At first I was
simply a spectator, somewhat at a loss, but in a moment I saw an opportunity as
James began kissing her neck. I replaced his lips on her and could sense in her
kiss the intensity of her excitement. While our tongues caressed each other,
James began stripping Nancy, unbuttoning her blouse, opening her skirt, and
exploring her body. In an erotic haze, we each managed to get rid of our
clothing and finally stood in a general embrace. James and I each sucked on one
of Nancy’s lush nipples, our hands encountered each other at her pudenda and at
the crack between the ample cheeks of her sexy ass. Bit by bit, without
speaking, James and I figured out how to share the erotic territory of Nancy’s
body with a degree of grace. One of us would stand and adore her breasts and
nipples and one would kneel and worship her labia, clitoris and anus. We
switched positions once and then Nancy asserted herself. She pulled me from
between her legs and the three of stood briefly kissing and embracing. I was
mildly surprised to realize that I was kissing James as well as Nancy and that
his tongue was in my mouth from time to time. The novelty and taboo nature of
all of this had my cock as hard as iron. I was in a haze of sexual excitement. I
found my right hand exploring James’ bottom as my left explored Nancy’s. Nancy broke off from kissing us to slide to her knees. She took my painfully
erect penis into her mouth first. While she sucked my cock, James began tweaking
my nipples and sucking on them. I moaned with pleasure. Suddenly, I found his
stiff cock with my hand and experienced a surprising thrill. I had never touched
another man’s dick and couldn’t believe the excitement I felt. Nothing could
have prepared me for what happened next. James slid to his knees and started
tonguing my ass as Nancy continued swallowing my penis. As I felt James’ tongue
penetrate my anus I thrust my cock down Nancy’s throat. I was in Heaven! All of this was a prelude to the ultimate point of the evening. I found
myself so excited that when Nancy rose and moved towards the bed, I was ready to
do anything to continue this degree of excitement. In bed, Nancy first arranged
James and me so that she could easily alternate sucking our cocks. Before long
she pulled me up and directed me to kneel over James and take his penis in my
mouth. Her pressure was gentle, but determined. I hesitated a moment but was
actually excited at the prospect. It was a handsome cock, richly veined, very
hard and looked quite a bit like mine. I’ve often thought, in my most private
thoughts while masturbating, that I’d be happy to have sex with myself, and in
James, I had something close to that. So I leaned forward, opened my mouth, and
welcomed his penis by swallowing as much as I could. Nancy made approving noises
and occasionally pushed my head down while she kissed James deeply. I became intensely absorbed in James’ cock. James and Nancy seemed very
absorbed in each others’ mouth and nipples, while continuing to enjoy my obvious
devotion to James’ dick. Nancy made several comments about what a good bottom I
was going to be, worrying that I might give up pussy for cock. After some minor
changes in position, we were ready for the main event. Nancy arranged herself
for missionary position and urged me to mount her. I was a bit surprised that we
weren’t immediately going to a double penetration position, and then realized
what Nancy and James had obviously planned in advance. I was so hard and
excited; I had no choice but to thrust my aching cock into Nancy’s totally
lubricated pussy. Next I felt James’ finger penetrate my already moistened anus
with a load of Vaseline. After working his load of lube in, James inserted a
second and then a third finger. In spite of my experience with anal penetration,
three fingers penetrating my anus so quickly caused me to gasp. In seems he knew what he was doing though. I never lost my hard on and pumped
Nancy’s pussy energetically. As my ass got accustomed to being stretched by
James’ fingers, I began responding as I did to Nancy’s strap on by pushing back
to increase penetration. As I began easily thrusting against the fingers, James
withdrew them slowly. I felt his hands on my hips and realized that he was
preparing to mount me. As the head of his penis began pressing against my
sphincter, I almost passed out from excitement. Since I was well prepped, his
penis was quickly buried in my rectum. I moaned like a bitch as Nancy held me
and James began fucking me. After my initial surrender to anal penetration, my
own cock asserted itself and the three of us established a mutually pleasing
rhythm. We fucked like this for a long, long time. I loved the feeling of my cock in
Nancy’s hot pussy and I loved the hard cock in my ass. Nancy would play with my
nipples and I would start thrusting reflexively. I would squeeze my sphincter
and James would thrust harder. We went back and forth, changing tempo, touching
each other in the most sensitive places. I felt like I could do it forever.
Finally, James brought things to a wild conclusion. He began spanking my cheeks
sharply – a new sensation for me. In seconds, the blood flow to my ass energized
and excited me to such an extent that I began pounding Nancy’s cunt wildly.
James grip on my hips tightened and his cock pumped my ass powerfully. As I
started to come, my sphincter tightened around James’ cock convulsively and his
thrusts quickened. Nancy started screaming, I started screaming and James simply
yelled. I don’t know who came first, but it was certainly a three-way come. We
screamed, we swore, we collapsed. We were covered in each other’s sweat,
panting, sighing, exhausted. After a few minutes, my diminishing dick slipped
out of Nancy’s vagina as she gave it a last squeeze. I continued to massage
James’ cock with squeezes of my sphincter until at last it popped out. I could
feel his semen trickling between my ass cheeks and felt incredibly satisfied. I
had drained his seed and satisfied him sexually. The sky was just beginning to show some light when I was awakened by the
insistent pressure of an erect penis between my ass cheeks. I moaned a bit, but
James shushed me with a hand to my mouth. He wanted this to be just boys’ play
while Nancy slept. His penis slipped into my stretched and swollen anus easily,
lubricated by the remains of Vaseline and a huge load of semen. We lay on our
sides, still spooning while James gently fucked me. Before long, Nancy’s eyes
shot open. She laughed. “No, really, it really turns me on to see you getting cornholed.
I just need to get off. Here I am in bed with two virile guys and they’d rather
fuck each other than fuck me.” After Nancy and James had each climaxed, they took turns sucking my cock,
trading it between their mouths, one sucking and swallowing it while the other
held the shaft and stroked. After I came in Nancy’s mouth, she shared my semen
with James in a deep, passionate kiss.
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