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
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