Copyright © jonniphillips2008

I thought you’d appreciate a brief look into my past

I’ve so enjoyed hearing your comments for the last few months that I thought you’d appreciate a look into my past.

Eight years ago as I was just starting to become comfortable in my transition. I went back to my hometown for the summer, after years of a rocky relationship with my parents, the plans got confused or miscommunicated, but in any case, my parents were away when I arrived. As I had done since I was a little boy, I called my mother’s best friend Jill from a payphone. Jill and my mother had been friends since before I was born. She was and is a striking woman, strong and confident in a way my mother never was. She had never married, but as a child you accept some things without questioning them. Jill was always there for me if my mother could not be, a confidant but also an authority figure.

Jill was there to pick me up in a few minutes and I went back to her house for the night. She asked about how I was doing, the usual things one asks a transsexual, and I answered them in the usual way. We had dinner, and soon were laughing over old pictures in the living room. We were on the floor in front of the couch, a bottle of wine between us. In the pictures, I noticed how beautiful Jill was at my age. And looking at her 30 years later, her clear blue eyes, natural blonde-turning-gray hair, her thin but fit body under a white blouse and black slacks, I could see she had not changed.

We must have sat like that, talking, for a couple of hours. I poured my heart out about going full time and passing and leading a 'normal' female life, my frustrations. And then she asked, “leading a 'normal' female life?” It was an odd question, and I laughed. She didn’t. “What do you mean?” I asked. Jill took another sip of wine, and asked, “Have you ever really made love as a girl, or just as a boy?” I looked at my glass and inexplicably became very embarrassed. I don’t know why I responded that way. The answer was I hadn’t thought about it, I had always been the penetratus and not the penetrated, her question made me feel somehow uncomfortable, as though I had.

Finally I looked back at her, and answered, “No.”Before I knew what was happening, she pulled my face close to hers, smiled, and kissed me – so gently – on the lips. A lightening bolt shot through me, but I could not move. My lips parted and I just stared as she stayed close, smiling. “Are you ok?” she asked. I said nothing. She sat back, covered her face in her hands and said, “I’m sorry, Jon. I don’t know why I did that.” I wanted to say something, anything. My heart was pounding, my palms sweaty, chest heaving, but I didn’t, couldn’t get any words to form, then, the moment that broke my heart and my silence… Jill started to weep. The woman who was like a second mother to me, only stronger, was sobbing into her hands from that one, gentle kiss. I moved toward her, kneeling in front, and quietly pried her hands away. She looked up at me through tears, and I kissed each moist eye. “No,” she pleaded. I looked at her, long and hard, and said, “Yes.” And then, the most sensual, romantic kiss I’ve ever experienced. Holding her cheeks in my hands, I kissed her deeply, slowly. I felt her tongue test my lips, then plunge into my mouth, exploring, tasting, hungry for me. I pulled back, reared up on my knees and pulled my linen dress over my shoulders. She wiped her tears and took in my body admiringly. I was in an plain bra, a little worn old and stained. My panties black and velvety soft. She let her hands move over my shoulders and down my arms, her finger tips grazing my hips, and then back up over my tummy. I closed my eyes, and felt her hands cup my breasts, then move to the clasp. The bra dropped clumsily between us, and I heard her whisper, “You are so beautiful, Jonni.” And I had never felt more beautiful, more feminine, more sexy.

Jill leaned forward and placed a tender kiss on my bellybutton, moving up past my sternum, pulling me close as she rose. Finally her lips locked on one nipple, already pert and aching. It was like I was being electrocuted. My back arched, my ass tightened, and my crotch thrust toward her. With one hand, Jill smoothly pealed down my panties, and the smell of my own sex wafted up between us. I looked down and watched her suckle my breast, and felt her fingers gently probe my thatch of sticky-gooey pubic hair. I pulled her head back and up and we kissed again as she fondled my penis and slid a finger around it. Before I knew it, she had maneuvered me back onto the couch, my tailbone on the edge, my legs straddling her shoulders. She had not undressed, had not had time. And I could see that my dripping had left little stains on her blouse. She kissed my calves, the backs of my knees, all the while gently playing with my penis. By the time her lips reached my tip, I wasn’t breathing, I was heaving. Her tongue explored me, nipping at my tip and then plunging deep around the shaft, over and over. My back arched, and it took me a while to realize the moans I was hearing were coming from me. I watched her, and she watched me, our eyes fixed on each other as she brought me closer and closer to my first orgasm. Soon she locked her lips around my sex and began to suck and lick. Then I screamed, from shock and pleasure. Jill had slid a finger, wet from my own gooey mess, between my clenched butt cheeks and into my asshole. I had never felt anything like that, and she hesitated. I started to breath again, relaxing my ass to give her more room. I caressed her head with one hand and encouraged her probing finger with the other. I am sure it was only 30 seconds, but what seemed an eternity later I came in shockwaves, over and over in quick succession. My knees locked, my toes curled – the force of it pushed me from the edge of the couch, and Jill had to hold me up. It felt like an i.v. of warm liquid poured into my body, I was high, numb and hypersensitive all at once.

Soon I was curled up on the couch, Jill naked next me, caressing my hair, kissing me gently. I tried to speak and found my throat raw, though I do not remember screaming. Jill just lay there with me, quietly whispering the most wonderful encouragements, the sweetest little compliments. We lay like that for some time, then bathed, climbed into bed, and I spent the rest of the evening exploring her, tasting her, knowing her. I’ll never forget the way she tasted, creamy and pungent – a sexy musk that coated my mouth. I remember the steamy-slick texture of her vagina, how she coached me, encouraged me. She taught me how to tighten and relax the muscles around my derriere; heightening my orgasms (I lost count of how many I had that night). She gave me free reign over her, experimenting in my own clumsy way. When we finally drifted to sleep in the wee hours, I can still remember that exhausted feeling. My face taut with the dried wetness of her sweet pussy, my jaw aching, my body slack and spent.

The next day, we made love one last time in the morning. That day, my parents came home and I left, returning to real life. I remember her musky scent was still on my fingers, and I let it linger through the day, breathing them in whenever I could. I still see Jill from time to time at my parent’s house, whenever I am back home, but we have never spoken of that night again. I suppose it was a special moment, unrepeatable, forbidden.