Formative Development of My Sexual Self

 

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.