Teenage Years - (Chapter 4 Part 5 - My First Girlfriend)

Having female friends was wonderful for me, I felt so comfortable in that "friend zone" but to be completely honest I started to feel some yearnings for more than just being friends. My biggest issue with moving forward was fear of rejection, and if I were rejected, losing the girl as a friend. In addition, the 5 girls in our little group felt comfortable with me as a friend that they constantly talked about boys they had "secret crushes" on, and I was nothing like any of those guys.

As time went on one girl, Elise, who was in 9th grade and the youngest of the girls started to make subtle advances like making sure she sat beside me, inviting me over earlier than the others, touching my arm, inviting me to go to movies or just hang out without the other. Naturally being so inexperienced and insecure I missed all these hints so eventually she just asked me if I wanted to be her boyfriend. You would think that since she was now my girlfriend, I would feel comfortable with taking the initiative sexually but again I was hesitant and insecure.   After a month all we had done was soft kisses good night until one evening while we were watching TV, she took the initiative and we started making out. 

Within seconds I had an erection, and I was in heaven, and it only got better when she took my hand and placed it on her breast and I started feeling her through her blouse. Things progressed slowly but now I was experiencing normal teenage boy sexual adventures. It was not long before I slipped by hand inside her blouses and then touched her bare breasts. Much to my embarrassment the first time she touched my cock through my pants and rubbed it I immediately had an orgasm. We were soon touching and groping every chance we had which was usually on Friday or Saturday nights when my mom went out on her frequent dates.

Since we were spending more time at my house now, eventually Elise noticed that my room looked like a girl's room and without really having an explanation why I told her that I liked to dress up like a little girl sometimes. I was both relieved and mortified when she told me that she had heard rumours at school that I liked girly things and that I wore diapers. I remember blushing horribly and figuring those things were over, but she didn't seem to care and she never said anything else about it.

For the next few months our sexual adventures were at the point where I would play with her breasts, and I particularly loved to suck on her nipples. She was now taking my penis in her hands and stroking me, but she never gave me a blow job. I didn't really care, and I always thought it was weird when I spied on my mom having sex and she was sucking her boyfriend's penis. My biggest worries were that I knew my penis was very small and much to my horror I was always having an orgasm very quickly.  

Elise almost always wore pantyhose, and I loved the feeling of them against my legs. I would often touch her legs and loved the sensation. I sometimes would cautiously let my hand slide up a little further up her leg and she would push my hand away.  She confided in me that she was not ready to have sexual intercourse and she was very self conscious about me seeing her naked or even being partially naked.   I begged her to let me touch her legs, bum and privates even through her pantyhose and she agreed. 

I think this is where my addiction to women in pantyhose began. I loved to feel her thighs through the nylon and especially loved to caress her bum while we made out on the sofa. I think it helped that I rarely pushed the issue and often she was the one who initiated our cuddling and groping time. Sucking on her nipples while I touched her pussy through the panties and pantyhose was our favourite activity. I would orgasm multiple times during these sessions which was both embarrassing and wonderful. 

We never ended up having sex but evolved to the point where she would leave her bra, panties and pantyhose on and I would be naked, and we would dry hump and I would rub my cock against her pantyhose covered pussy in a missionary style or I would rub it against her bum in doggy position or just rub myself against her pantyhose covered legs and cum over her pantyhose.

We dated for over a year until I graduated high school and moved back to North Vancouver with my mom where I would attend Capilano College.  Our little group stayed together the entire time and none of the other girls said anything or seemed bothered by us dating. 

Elise was self conscious because she was a larger girl, she was tall and well developed with a big round ass and large breasts. Eventually we would spend time in bed, and she would not wear her bra and I lovingly suckled on her nipples for the longest time while my hand caressed every part of her pantyhose covered legs, bum and pussy. Eventually she told me and showed me what she was most self conscious about after much begging and pleading especially after I shared about my desires to wear little girl clothing and my diaper desires. 

One day when we were groping, she took my hand and slid it inside her pantyhose and placed my hand on her pussy. Elise had very large pussy lips that hung down as well as they were very swollen. I was touching my first pussy and had no idea that this was unusual.  She guided my hand and showed me how to make her feel good and then she guided my hand to her clit which I could feel was sticking out in between my fingers.  I will never forget the day I made her have an orgasm by guiding my hand and fingers between her legs.

To this day I love a woman in pantyhose and have been fascinated by large swollen and long hanging lips.  Little did I know that her large swollen and low hanging pussy lips was very uncommon, and I never again had the pleasure of seeing and touching such lovely pussy lips.

Elise's pussy lips were almost this large and swollen

Teenage Years - (Chapter 4 Part 4 - My Friendships with Girls)

Not since my early friendship with Erin did I feel comfortable around girls but now I was surrounded by girls 3-4 afternoons a week after school and I was loving it. We had common interests and there was a level of comfort. I think the fact that they all knew I was different and for the lack of a better word was a “sissy” they felt comfortable and not threatened by me. 

For the most part I felt more comfortable around the girls that were younger than me. I still felt uncomfortable with the girls in my grade and 12^th grade because they were more mature and all they talked about was boys. It started off innocently with girls asking if I would like a ride home with their mom at the end of the club time.  With the school being very Christian oriented they were friendly and welcoming.

It was not long before a group of us started getting together on weekends in the afternoon to cook and bake together at a different person’s home each weekend. Since it was mostly the younger girls and I getting together it was very casual and carefree without any pretensions of there being any interest in dating or romantic interest for the most part at least by me. Looking back though I should have caught onto the signals from a few of the girls such as them touching my hand or arm often and hugging me when we saw each other or left.

When we had the cooking/baking gatherings at my house I noticed that my mom was very happy to see me enjoying myself and feeling comfortable. She was perhaps a little too friendly and

was around us more than I had wanted. Since my room was right beside the bathroom, I was worried that one of them had seen my room when they had gone to the bathroom earlier.  I didn't want my friends to see that my room was one of those little girl rooms complete with canopy bed that was so popular in the day and in the Sears catalog.I was so upset with my mom, and she claimed that she had left the door out of force of habit.

When I finished complaining to my mom and returned to the kitchen, I was mortified to see out through the sliding doors of the dining room which faced the backyard that my mom had hungout the laundry to dry on the clothes line because it was a nice warm

October day. Amongst the towels and sheets, she had also hung my diapers plastic pants, ruffled panties and one of my frilly dresses. I went running to my mom and she again claimed that she had forgotten I had friends over and she quickly took down my clothing.

When I returned to the kitchen none of the girls said anything but there was no way they didn’t see them because the kitchen window overlooked the backyard, and the clothesline was in full view. I was so upset for the rest of the day not just because I was so embarrassed but also that I worried that I would be shunned by the group.

Thankfully nothing seemed to change. Over time we started going to movies together and other activities almost every weekend. A couple of the girls were even in a square dance club, and they invited me to participate. I remember they were shocked that I knew how to square dance already. Alas when I attended, I dressed and acted like a male partner. Seeing the girls in their crinolines, big puffy dresses and getting peaks at their ruffled panties inevitably had me develop an erection and when I got home, I often would put me outfits on and enjoy the feelings of wearing frills and ruffles. I would often lay on my bed and rub myself through the ruffled panties until I would cum in my panties. 

Our little friend group remained intact until I graduated, and I even stayed friends with a few of the girls after we had moved back to North Vancouver, and I began attending Capilano college. In fact, I remained close to two of the girls into my early 20’s and had begun the next chapter in my sissy life.

 

Teenage Years - (Chapter 4 Part 3 - Accepting my Feminine Role)

As 11^th grade progressed, I began not to feel ashamed about my interests in things that were not stereotypically male. While it was not all wonderful times, I felt better about myself as I got older, sure there were times that I was ruthlessly teased and bullied at school I ignored it as best I could. The teasing and bullying did bring the stress induced wetting again so I often wore thin cloth diapers and plastic pants to school and the nighttime wettings became more severe. I loved cooking, cleaning, and sewing it brought me comfort and I was very good at it. I don’t feel that there was a correlation between the interest in traditional female roles with the home and my love of feminine attire they were mutually exclusive. I was a home body and I found that cooking and cleaning were relaxing.

I was never so happy as when I was at home doing traditionally female chores and activities. Little did I know that in a few short years I would

have that opportunity when I met an older gentleman who nurtured and encouraged my feminine desires. It was also at this time when I first saw on TV a provocative maid's uniform during a skit on a comedy show like  Benny Hill.

While I was not athletic in the normal sense when it came to sports, I had a natural aptitude towards golf. My parents were members of a private golf club in North Vancouver and when I was younger, I would tag along and play or go to the driving range. Even then I seemed to have a natural aptitude towards the game. When my mom starting dating when I was in 11^th grade the man, she was dating was an avid golfer and she encouraged me to go along one Sunday afternoon to Mission golf & Country Club where he was a member. I think part of it was to help us get to know each other better. Apparently, he thought I was some sort of prodigy because I shot I the low 80’s and had not played golf in probably 4 or 5 years.

He encouraged me to try out for the school golf team that spring, but I was not interested in being art of the “guys” at school. I continued to play golf casually during my last two years in school, but I preferred to go play late I the afternoon by myself or I just joined up with adults rather than play with people nearer my own age. 

Even with golf I remember wishing I could wear the skirts or dresses that the players on the LPGA Tour wore but alas that never happened.

Teenage Years - (Chapter 4 Part 2 - My School Guidance Counsellor)

When my mother and I joined the church which was indirectly associated with school my mother was very open with both and let them know that I was not a normal boy emotionally as well as other things. I don’t think gender identity was even a term then but I’m sure that’s how I would have been classified now. I personally don’t think I had difficulty identifying with my gender I just enjoyed frills and girlish clothing and that role.

I was assigned a Guidance Counsellor when I arrived, and I was blessed to have been assigned a lovely younger lady rather than one of the traditional old school types. The counsellors were there for emotional support and help guide us through our teenage years. Looking back there was a heavy emphasis in making sure we towed the religious line according to the church doctrine. In simple terms no drinking, drugs, sex, no rebellious behavior, and volunteer for church, school, and community-based activities.

Miss Brown was so kind, and she understood I was struggling socially, and she really encouraged me to join some of the many small clubs that the school and church organized. Other than golf I was not interested in anything that remotely was focused on boys, so she asked me what I enjoyed doing at home and on weekends. I was embarrassed to admit I loved cooking, baking, sewing things with my mom, etc. All clearly very traditional female activities.

I ended up going the Baking Club, Cooking Club and Sewing Club in 11^th grade and I struggled to fit in the first month or so, naturally I was the only boy in these clubs. There were lots of giggles and snickers from some of the girls, but Miss Brown gently prodded me to keep attending as well as sit with any of the girls who were shy or appeared to not be fitting in as well.  I suspect Miss Brown spoke with the teachers who were leading the clubs because the next time I attended each of them suggested I sit with a specific girl.

Teenage Years – (Chapter 4 Part 1 – Discovering My Direction)

In the weeks leading up to the start of 11^th Grade we receive Aptitude and Vocational Testing followed by meeting with counsellors to go over the results and on the first day of school there was a Career Day where we could meet with people working in various industries.

My Aptitude Testing results showed that I was number oriented and analytical but did not have an aptitude toward sciences and the general feeling was that I would be most suited for Business and Accounting which was not surprising because I had taken a course in basic bookkeeping in 10^th grade and loved it.  As a side note the alternate field recommended was in the service industry.  Ironic considering that three short years later I became a “sissy maid”. (That will be the next chapter of my blog)

Going to university for 4-5 years to obtain a Bachelor of Commerce degree did not appeal to me in terms of time involved but also, I did not want to be required to take loads of math and a few required science courses. I also knew by then that I really wanted to get some freedom and get away from my mother. There was no money for me to live on campus either, so my inclination was to enter the Business Management programs at either BCIT or Capilano College. Since I would not need to take as many prerequisite courses to qualify for university I focused my courses during my last two years in high school on accounting, bookkeeping, typing and economics. Being a very traditional based school, they offered lots of courses in Home Economics and while my academic counsellor saw no harm in taking those although I remember him saying it was a little unconventional for a boy to take courses that were geared towards girls. Being the late 1970’s things were still pretty gender specific which was exacerbated by the traditional nature of this school.

Teenage Years – (Chapter 4)

 As I entered 11^th Grade in September it was the start of many changes for me socially, my sexual interests as well as general development. There were so many different factors that all came about within a short period of time:

             1.    Discovering my direction.

2.    My school guidance counsellor.

3.    Accepting feminine role

4.    Girls were my primary friends

5.    My first girlfriend

6.    Masturbation

7.    Discovery of lingerie catalogues

8.    Exhibitionism

9.    Learned about sex

10.  Sexual awakening

11.  Corporal punishment

             12.  Return to Vancouver

Rather than write about my last two years in school chronologically I thought I would share these topics individually.