Boys Will Be Boys - Their First Time (33 page)

“
Mmmm,
”
was all I could say in agreement. It was then that I wondered what it would feel like to let him cum on my face, but that would have to wait for a future agenda. The thought of doing that, however, got to me
,
and I had to start jerking off.

Scot took control then. The kid fell forward and slid my cock into his mouth. I, wanting to suck all day and night by now, started blowing him again. We sixty-nined in that position for about twenty minutes
,
and seconds after he came again, I signaled him that I was ready to go off, too. So he masturbated me until my load was spent.

* * *
* *

The next day, I found out how erotic it is to slip a condom onto someone
’
s rigid dick while devouring his young, muscular body with my eyes. I gave Scot
’
s scrotum a few caresses before reaching for the tube of KY-Jelly and saying,
“
This will make it go in easier.
”
Not having known about prepping the anal canal first, I heavily coated his rigid shaft and got onto all fours with a smile of anticipatory excitement.

Surprisingly, Scot
’
s glans entered my virgin anus with little discomfort. I told him to ease it in and out to stretch my sphincter muscle, and he did so while purring continuously. Since I had already sucked him to two orgasms, the kid wasn
’
t likely to cum too fast this time. Or, so we thought.

I loved every moment of that wonderful act
–
the way the ridges on his shaft rubbed my anal ring and made it tingle, the way his thighs slapped against the backs of mine, the way he tightly held my hips.
I didn
’
t want to stop.
“
Oh, Scot, that feels so good. Keep fucking me just like that.
”

By the time his stiff, six-inch shaft had been riding in and out of my anal canal smoothly for about five minutes, he groaned and said,
“
I can
’
t hold off anymore. I have to cum.
”

Keep fucking me fast,
”
I practically begged. I repeatedly thrust my hips back to meet his every inward plunge while wondering why I hadn
’
t begun doing this at a much earlier age. How could some people not like anal sex?

“
Ah!
”
Scot cried out while plunging his cock as deeply into me as he could, which caused his balls to slap against mine. His strong hands gripped my hips so tightly that his fingernails almost dug into my flesh.
“
I don
’
t believe this,
”
he panted.

I thought I was going to cum just from the excitement of feeling his cock contracting inside of me. For some reason, mine had wilted, but I started jerking off anyway.
“
This is great, Scot. It
’
s great. I love it.
”

With his load spent and his dick wilting inside of my ass, I got an idea.
“
Try to sit without letting it pop out of me.
”

He managed to slide his lower legs between my knees, pull my hips back and sit. Now we were both in a sitting position with me on his lap and his dick trapped in my ass.

“
That was totally awesome,
”
Scot sighed while I was putting his hand on my cock. He got the hint and masturbated me while we began talking about a few more things we could do together.

Ten minutes later, I was fully hard, and it only took a few more minutes for that young stud to get a full erection again. This time, though, he lasted much longer.

We took an uneventful shower together about a half hour later, got dressed and returned to my recreation room. I enjoyed having Scot around. Aside from the sex, he was a welcome relief from the pressures I usually had to endure at work. Maybe part of the reason was that I felt a lot more comfortable with him than I had felt with female friends.

When, during our casual conversation, I mentioned enjoying fresh water fishing, Scot
’
s eyes lit up.
“
Really!?
”
he exclaimed. I used to love to do that when I was a kid.
”

“
Why don
’
t we spend some time drowning a few worms?
”
I offered. He readily agreed, and we also planned on taking in a few baseball games, too. This was turning out to be a great relationship.

* * *
* *

It wasn
’
t until two weeks later that Scot was lying on his side with me behind him. With my having used two heavily lubricated fingers to stretch his sphincter muscle while blowing him on a daily basis, I didn
’
t expect this to cause too much discomfort.

He slid a thigh back over mine; I pressed the head of my heavily lubricated, condom covered cock against his anal ring. Being as gentle as possible, I eased two inches into him while caressing his balls. Probing slightly deeper with each inward thrust, I soon felt him relaxing completely. A minute later, the full length was in him, and I was slowly masturbating a man who was continuously moaning in ecstasy.

Scot had been a perfect male lover back in those days. He had a terrific body, a terrific cock, a pair of rapid recovery balls. He loved to suck and be sucked; he loved to fuck and be fucked. It was too bad that he had to move away after graduating from college to take a job in another state.

* *
* * *

But now, Scot was back in my life since he had transferred to a local branch office. He was married but said something was missing in their sex life. I knew what he meant and had no objection to us spending some time together. So, what was to stop us from picking up from where we had left off?

271

Mickey Erlach

I guess it started one Saturday morning in a small boat on the Long Island Sound. Our luck hadn
’
t been running to
o
well, so Robert, a coworker, and I just talked about nothing in particular.

When I asked why he never dated any of the women in the office, he thought for a few seconds before giving me the first hint.
“
I guess,
”
he began slowly while gazing off at the plastic ball near the end of his line,
“
you don
’
t really know what I
’
m about.
”

The comment went over my head like a flock of gulls.
“
No,
”
I said,
“
I don
’
t know what you
’
re about.
”

Rob smiled, giving that macho look to his rugged face. Then he clasped his hands behind his head, causing his arm and chest muscles to expand, and leaned back until he was resting against the bow of the boat.
“
Want to find out?
”
he asked, seeming to be daring me.

Although I said nothing, he must have detected some interest in my eyes.
“
I
’
m going to a house party tonight ... over on the Island,
”
he said nodding toward
Fire Island
.
“
Why don
’
t you come with me?
”

* * *
* *

By the time I had walked halfway through the spacious living room of that
Fire Island
mansion, I knew what Robert was about. I seemed to be the only straight person among about two dozen gay men and women, even though, judging by some of their mannerisms, I couldn
’
t tell which was which.

It was about two hours later that I met Candy. Suspecting she was a lesbian, I didn
’
t bother making a play for her, not wanting some bull dyke tearing my head off. So, we talked and talked and talked.

All the while, though, I was checking her out. What a shame, I thought. She was a blonde, about five
-
six, and had a pretty face, voluptuous lips, small but nice boobs, a slender figure and nicely shaped legs that showed themselves provocatively from the bottom of a snuggly fitting mini skirt. What a waste of flesh. That woman had been meant for a man.

“
It
’
s kind of warm in here,
”
she said with a soft, sensuous voice that sent pulses of electricity through my nuts as if I had never gotten laid in my life.
“
Care to get some fresh air?
”

* *
* * *

Candy and I walked toward the boat dock without talking. When we got there, she sat on the edge and leaned her back against a post. I was about three feet away, facing her with a knee extended in her direction, possibly to assure her I would keep my distance.

While I was busy watching the moonlight reflecting off the rippling waves and washing over her cover girl face, she spoke.
“
So ... what do you think of the scene in there?
”
Her floating hand lazily pointed to the house.

Wanting to be honest with her, I simply said,
“
It
’
s not for me.
”

“
And,
”
she asked,
“
what
’
s with you and Robert?
”

I returned her smile with the feeling of lust growing within me at the sight of her pure white teeth and perfectly shaped mouth.
“
I hadn
’
t known before tonight that he was gay. Er ... that is, I guess he
’
s gay, considering his other friends.
”
I didn
’
t want my remark to be interpreted as a derogatory one. Noticing the lack of hurt in her face, I continued.
“
I think someone like you is more my style.
”

“
I
’
m ... not a woman,
”
she said with no apology meant while her blue eyes pierced my heart.

Candy explained that the lack of hair on her face and body was from electrolysis treatments and female hormones, the latter of which had also developed her breasts slightly. Surgical implants had brought them to the thirty-four B size they were now. She also told me that she was living with a lesbian.
“
Ironic, isn
’
t it?
”
she asked.
“
She loves women and wishes she were a man; I prefer men and wish I were a woman.
”

I was dumfounded and could only think of asking,
“
Wh
…
why are you telling me this?
”

When Candy smiled at me in that sensuous way, I still wasn
’
t sure I believed her. I thought she was putting me on until she explained further.

“
Well, inside the house, I got the feeling you wanted me as much as I want you. And I wouldn
’
t want you to be disappointed if you were to kiss me and put your hand inside my skirt and find a pair of balls.
”
She giggled lightly and put her fingertips in front of her mouth in a totally feminine manner.

I had to laugh with her, but our nervousness made us continue chuckling out of control for a few more moments. Then I could only escape behind a barrage of intellectual questions.

“
Are your breasts sensitive like a woman
’
s?
”

“
Definitely.
”
Candy smiled and brushed the tip of her tongue across the edge of a sensuous upper lip in a way that would have forced me to kiss her had she not been a man.
“
In fact,
”
she added,
“
if it weren
’
t so dark now you
’
d see that my nipples are in quite an excited state.
”

I took a deep breath and reminded myself that Candy was a man.
“
But, can you still function as a male?
”

“
Sure I can.
”

“
I mean, do those female hormones you take
…
prevent you from …?
”

“
No, I can still get an erection, and I can ejaculate.
”
She looked at me, appreciating my interest.
“
In fact, that
’
s the one big contradiction in me.
”

When I looked at her questioningly, she continued.
“
I like to be made love to by men, but I also love to perform anal sex on a guy.
”
Seeing I still hadn
’
t run away, she pressed onward.
“
Are you a virgin?
”

“
Yes,
”
I said shyly,
“
with the exception of a woman
’
s finger or two.
”

“
Did you like that?
”
she asked, turning sideways and extending a knee toward me.

For a few moments, I looked at the part of her thigh that was exposed below the hem of her miniskirt and felt my mouth filling with saliva. I couldn
’
t believe I was thinking like that while talking to another man. She
’
s not a man, I tried to convince myself. She is a woman. And, besides, what
’
s the difference whether you make love to a woman and suck her cunt or to a woman and suck her cock? Did I really ask myself that? I finally answered her.
“
I liked it very much.
”

* * *
* *

The next day, although I still had some reservations, or maybe I was just nervous, Candy and I had lunch in my apartment. She had agreed not to push, and I had consented to our getting to know each other a little better. After all, we had enjoyed talking the night before
.
W
e could be just friends
.
N
either of us was really starving for sex.

Candy filled a pair of jeans nicely, and her soft knitted blouse revealed the absence of a bra and the excitement of her nipples as she slouched into the corner of my sofa. While she was studying me with a provocative gleam in her eyes, her lips were pouting slightly, which made me want to kiss them, something I never would have considered doing before we had met.

With an uncharacteristic high degree of control, however, I managed to resist the urge to do that, even though I knew we were probably going to do something. But what? I can just let her suck me off. No, that wouldn
’
t be fare. I can play with her tits while she does it to me
,
and she can masturbate herself at the same time. Would she be satisfied with that? Lots of street gays give blow jobs in men
’
s rooms and get nothing in return. But she
’
s nothing like them. Well, maybe I can give her a hand job. She knows I never did anything with a guy before and probably won
’
t be expecting more than that. We
’
ll see. She also knows I had enjoyed fingers in my ass. Is she expecting to fuck me in the ass? Hmmm
t
hat might be interesting.

“
Do you like to get high?
”
Candy asked nonchalantly during a brief lull in our conversation.

Knowing where she was going with that one, I smiled while remembering the first girl I had fucked after having gotten her slightly drunk on beer. Then I realized that might be the best way to break the ice.
“
I haven
’
t smoked pot in quite a few years.
”
My eyes focused on her nipples. They had grown even more within the last few seconds.

“
I have some in my handbag. Want to try? It may be just what you need to relax.
”

“
Am I that obvious?
”
I felt myself blushing.

“
I want you,
”
she said seductively,
“
even if you don
’
t want to touch me. Maybe, after awhile, you
’
ll loosen up.
”

A few seconds after I agreed, she moved closer to my corner of the sofa, touched a match to the tip of a thick joint, held it between her delicious looking lips and took a few hits while staring into my eyes with a
“
come and get me
”
look. Then Candy leaned across my chest and dropped the match into the ashtray on the table next to me.

When she did that, a soft breast brushed over my arm, and I was up to sixty percent sure we were going to do something that day. I wasn
’
t even stoned yet, but I wanted to grab Candy
’
s tits and slide my cock into her mouth where that joint was. It took a few deep breaths to calm my racing heart.

Candy handed the weed to me. I took a long drag, held the mild smoke in for about a half minute, exhaled some and took some more. I needed it because I wanted her and didn
’
t want to change my mind now.

When the reefer was too small for me to hold, Candy held it between her long fingernails and said,
“
Open your mouth.
”
I did so; she took a hit and move
d
closer.

Knowing what she wanted to do, I parted my lips and accepted the smoke she blew between them. While doing that a second time, her sensuous mouth was only a fraction of an inch from mine, and my cock was getting hard. It was the third toke that did it, though.

After taking a drag that lasted about three seconds, Candy slowly passed the smoke to me. I don
’
t know if I closed the gap between our mouths or if she did
,
but before we knew it, our trembling lips were sealed together. A purple cloud was surrounding our faces while her hand was resting against the back of my neck and mine were exploring her small, but soft, breasts. Damned if I wasn
’
t kissing a man and loving every moment of it.