My recent correspondence
with others has lead to a number of the men I am sharing my life story with has
lead to questions about my status as either a sissy or cuckolded man while
married.
Although previous blog posts
I have talked briefly about my experience spying on my mother having sex as
well my disastrous attempts at dating I thought I would expand on my feelings
as well as when I went for therapy in later years what impressions I was given
by the therapists.
I knew nothing about sex at
the time, I was about as naïve as a 10 year old when it came to sex I hadn’t
even seen a Playboy or Penthouse magazine at that point in my life. I didn’t
have male friends growing up and learned about the basics of sex like most guys
did by talking and hearing about their time exploring sexual feelings with
girls our age. Instead I was almost an adult and now I was learning about sex
and to make it more unusual it was from frank discussions with my mother,
spying on her having sex and then with my first sexual relationship with Dr.
Allen.
That period from 18 to 20
year of age had a huge effect and lasting on my sexuality, how I viewed sex and
how I saw myself in sexual relationships. I was now an adult and my mother was
very open with me about sexuality and my identity. She was very reassuring and encouraged me to be open with her. She even
arranged for me to see a therapist who dealt with gender identification issues.
The therapist did not feel that I was transgendered but rather someone who
enjoyed crossdressing with a desire to regress. I remember the therapist
explaining to me that being a TV or CD did not mean that I was gay or even
bisexual it was a fetish towards women’s clothing.
I did some research at
college but everything was very clinical and did very little to help me
understand if what I was feeling was normal or not. What I did know was that I
definitely leaned towards enjoying the female or effeminate side of sexual
relations rather than the male.
The timing of this partial
awakening coincided with my mother beginning to date a pastor from our church
and for the first time in years there was a male influence in my life. My
parents were not affectionate towards each other but Pastor Eric was extremely
affectionate with my mother when he came over on weekends and one or two
evenings a week. They were constantly holding hands, he would whisper into her
ear and she would giggle or blush. When they were side by side he would often
squeeze her bottom when he thought I was not looking and other times when I was
I the other room I could hear him give my mom’s bum a sharp slap and she would
playfully say something. Even when they watched TV or just sat on the sofa
together they were always side by side and his hand was on her thigh and
sometimes I spotted it up higher and inching under the hem of her dress. Mom
would playfully push his hand away but I still noticed it and shortly after she
would tell me that it was time for bed.
At first I hated going to
bed but soon I didn’t mind because when she sent me to bed it meant they wanted
privacy to make out which lead to sex which I always listened to from my
bedroom next to hers and increasingly would watch through the partially open
bedroom door.
The very first time I
watched them having sex from the dark hallway I was caught and that lead to a
very embarassing and frank discussion about sex from my mother. It was not a
clinical discussion but rather about how couples enjoy sex and some of the
things they enjoy which are all part of a relationship.
I was fascinated by their
interaction together, he had a strong influential demeanor and my mother seemed
to be so happy in his presence. I often fantasized about being treated that way
by a man rather than being a man and treating a woman like that.
We had many very frank and
open discussions about sex and male/female relationships. It was a very
stressful time for me because I started to realize that I was different than
other men but I was terrified to tell her
because I feared what she would think. One evening she asked me to come
to her bedroom and she asked me since I did not think about girls if I thought
about being with a man. I immediately blushed and shook my head but she
persisted and I broke down in tears and told her that I thought of myself as
being a girl not just dressing like one but also in other ways.
She was very reassuring and
told me that she figured that might be the case years ago because I never
objected to dressing in the frilliest of girl’s clothing plus I really took to
doing domestic chores that women traditionally did. She brought up me watching
her with Pastor Eric and gently asked if I liked what he was doing with her.
Being naïve I thought she meant about
him kissing her, holding her hand and other things and told her that I did. She
asked about what she saw them doing in bed that one evening and I blushed even
more. I said I did and imagined myself being the woman.
I was pretty upset by this
all and she told me everything was fine and she explained homosexuality and
bisexuality to me. She reassured me that she was not upset and that she would
help me learn about how to please a man because before I knew it I would
possibly meet a man. She explained to me that I was quite effeminate and what
people call a “sissy”. I loved doing the traditional female chores and roles
within the house. I loved cooking, cleaning, going grocery shopping and I even
loved to tag along with my mother when she went shopping for clothing. All
things a normal 18 year old boy would enjoy.
This was the early 1980’s
and there was minimal openness towards crossdressing, transvestitism but
certainly not homosexuality and fetishes in general. I remember feeling very
relieved when she explained to me that
men can also take the role of being a “wife” in a relationship with other men,
I told her that I liked that idea of dressing and being like a wife to an older
man. She vaguely talked to me about what being a “wife” or sissy entailed and
that it would be difficult to find such a relationship.
I know it sounds bizarre and
creepy but I was fascinated by the sounds of them having sex. You would have
thought that the fact I was caught spying on them would end my voyeuristic
desires but it had the opposite effect. Since my bedroom door was open and our
home was quite small I could hear them chatting and giggling in the living
room. It was not long before the chatting stopped and I could hear soft moans
and the sound of kissing. Soon after I could hear them go into my mom’s room and
the sounds were much louder. They always had sex with the bedside lamp on and
the door partially open. When I started to hear the bed squeak and the
headboard banging against the wall I would sneak out of my room and peek into
their room from the dark hallway. The way the bed was situated in relation to
the door made it that I was slightly behind the, so they could not easily see
me.
They almost always had sex
doggie style and Pastor Eric would make love to her very aggressively. He would
grab her bum, her breasts and sometimes her hair as he made love to her. He
would tell her what to do and physically flip her over to change positions. I
found this so exciting especially when she was on he back and he would kiss her
as he pumped his cock into her.
Oral sex confused me and frightened
me again he was always quite aggressive and almost demanding. He would hold her
head as she sucked him and often it looked like she was making love to her
mouth.
About a year later when I
just turned 20 I had my first sexual contact with a man. To say I was
frightened that first night would be a huge understatement but I knew I was
ready and I desperately wanted to experience being the “woman”. Looking back I
was so fortunate that Dr. Allen (or Uncle Allen which he preferred to be
called) was kind yet forceful. His demeanor with me was so similar to Pastor
Eric’s with my mother that I could feel myself drifting into a totally
different headspace very quickly. He was very kind, soft spoken and caring
however if I misbehaved he was like a very strict daddy. Sexually he was
assertive and did not take kindly if I hesitated or shook my head and said
“no”.
The first time he held me,
slid his hand up my leg and under the dress I was wearing I remember at first
tensing and pushing his hand away tentatively but he persisted and gave me a
warning look. He held me, cuddled me and I remember feeling very relaxed in his
arms. When it was time he took me to his bed and undressed as I sat on the bed.
Without a word he took my head between his hands and pushed his cock between my
lips. I started to do what I saw my mom do to Pastor Eric but I clearly was
terrible at it. My teeth raked across his cock a few times which angered him
and he pulled out of my mouth and gruffly told me to lick and suck his penis as
if it were an ice cream cone on a hot summer’s day.
I immediately loved the
taste of his penis and I really liked the soft skin of the head. IT was not
long before something happened that I was completely unprepared for, without
warning he pushed his penis into my mouth and it filled with his cum. I was
mortified and frightened as he filled my mouth. I never had seen Pastor Eric
cum in my mom’s mouth and I started to pull away. Uncle Allen firmly told me to
swallow everything and any that leaked out he wiped with his fingers and put in
my mouth.
While I was initially
revolted by this sexual act he was so reassuring after, he held me, stroked my
head and then gave me my first passionate kiss. His tongue explored my mouth
and I felt so girlish for the first time. I let out a soft moan and again felt
limp and safe in his arms.
Later that evening me made
love to me for the first time in a manner that I had witnessed with Pastor Eric
and my mother. I flinched when he inserted his lubed fingers as I kneeled with
my bum high I the air and my chest against the mattress. I could not imagine
receiving his cock and without warning I could feel him pressing it against my
“sissy pussy”. Like any virgin I let out a gasp when he slowly pushed inside me
and after a few minutes to allow my sphincter muscles to relax he started to
make move to me. Yes it hurt initially but soon it did not. I felt like I was
in my sexual place having a man inside me. I loved the thrusts of his hips, his
thighs and balls slapping against my bum and especially his weight against me. I
remember my male persona drifted away as I closed my eyes and experienced what
it must feel like to be a woman. This orgasm inside me felt lovely, he held me
and kept his penis inside me while it softened and soon there was the feeling
of his cum dripping out of me as we cuddled in bed.
After that day I knew that
what I had been feeling as a teenager was indeed true and that I was happiest
as a submissive sissy in the care of an older man.
