Helen is a good friend of mine. When the following occurred, Helen and I had known each other for only a couple of weeks. We met at a party a mutual friend of ours was hosting and we instantly connected. To describe her, she was smoking hot. She was a blonde in her late 30’s with piercing blue eyes, huge tits, firm ass and I believed to be a closet lesbian. She was married to a man and had two kids. What scared me the most was that she was a she! I have never been attracted to a girl but she was hot, she was different. I am bisexual but more on the straight side but I can say that Helen was a hot gal and I wanted to maybe see if we could do anything together.

When we found ourselves alone at the party and grabbing food in our friends kitchen, Helen and I began small talk. She asked if I was transgender. I told her the truth, that yes I was and asked how she knew. She said that she would never have guessed that but Luci (our mutual friend) had told her. Before I could say anything, she said, “it’s fine, I love that you’re talking to me and you look amazing, would love to see that body in action!” I smiled. She asked what I did for a living and I told her I worked at the Massage Parlor.

“Oh my god!” Helen reacted, “you should come over one day and give me a massage.”

Of course I said yes and we exchanged phone numbers and she would call when she was free.

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2 weeks later… she texted me saying her husband and kids were going shopping together and asked if I could come over. I was really excited. I wore my sexy shirt with a pantyhose and took a Viagra pill before leaving my house. I was going there for sex, I knew she would only call me for that reason as well.

As I knocked on her door, I met her husband and their two children. I introduced myself to him and he said his name was Mike. They were just about to leave for shopping and told me to wait at the table for Helen to come.

I sat at the dining room table for a couple of minutes and was met with Helen. My erection began to induce and I was starting to get horny. I turn around and I was shocked to see her wearing nothing but a towel covering her body. She was half-naked already! She got us both a glass of wine before sitting down at the table next to me.

We talked for a little while, that’s when Helen started complaining of stiffness in her neck and back, so I decided and offered to massage her neck and shoulders for free. She turned her chair around and faced towards the table. I stood up and walked behind her.

When I put my hands on her shoulders, there was an instant reaction almost like an electrical current. It felt good to touch her and as I began to caress and knead her skin; her body began to melt. After a while I worked lower down her back noticing that she was becoming more responsive to my touch, sometimes softly moaning and sucking in air, occasionally providing almost inaudible encouragements of “Mmmm, that’s nice!” At her lower back I slowly, half massaging and half manipulating the towel, slowly slid my hands under the soft toweling and caressed her hidden back.

Helen’s skin was smooth and hot. She grew silent as my hands moved lower and I worked the towel farther down her back, baring more of her exposed body. Occasionally I allowed my hands to move along her sides, rubbing the small rolls of flabby skin under her arms; baby fat. I heard her moan when I reached around and rubbed her stomach. Bringing my hands back, I pressed my finger tips into her skin and kneaded all around her back, continuously putting pressure on the knot and knowing that it was gradually loosening. Helen moaned repeatedly as I slid my hands all the way up her back, taking the towel with me. Then, boldly, I rubbed outwards from her neck, over her shoulders and across the knot that held the towel together.

Once again I rubbed upwards, allowing my hands to rub more towards my Helen’s sides. She sighed whispering, “That feels so good!” as I tentatively bent forward and nervously kissed her neck in several places, moving up to her shoulders whilst I continued massaging. Helen’s towel which was covering her body seemed to be getting in the way of my kisses and my massage area. Suddenly, the knot slipped and the towel fell away from her body. Helen gasped, holding the towel over her breasts while I continued to massage her naked back. Then, to my amazement, she just sighed and placed her hands on the table in front of her, letting the towel drop to the floor. Now I had a clear view of her large sagging, pendulous breasts crowned with long hard crimson nipples hanging from her chest. I immediately slid my hands down over her shoulders and cupped them both, pinching her hard nipples as I sighed in her ear quietly. For the next five minutes I squeezed her breasts, manipulating them and watching over her shoulder as her nipples hardened even further. I continued to massage her neck and shoulders, occasionally moving around to her top half of the body and focusing the breasts as well. She continued to breath harder and moan louder.

Helen turned around and said that we should go to the bedroom. I agreed. We walked together, hand-in-hand with her naked to the family bed and we both hopped on. She laid down on her back putting a pillow under her head and putting another pillow under her butt. She wanted me to eat her matured hairy pussy out!

I nod my head and she moves her hand to the bed again. I look down at her pussy and lick my lips. I hesitantly lean forward and run my tongue up her slit. She moans encouragingly. I do it again but harder and she moans again. I move my tongue in between her pussy lips and find her clit. She jerks slightly as I touch it with my tongue, I thought I hurt her so I pull away.

“Did I hurt you?” I asked as I look up to her. She smiles slightly and shakes her head.

“No, my clit is just very sensitive.” She replied.

I smile a little and bend her legs up. “So that means I should be gentle, yes?” She smiles and nods her head as I grab her hips slowly. I kiss her pussy lightly and she gulps.

“Yes.”

I nod my head slightly and take her advice. I lean forward and gently find her clit again. I start to write the alphabet in cursive on her clit. She immediately moans and moves her hands to her breasts to squeeze and pinch her big erect nipples. I move my tongue faster in cursive and she gasps slightly. She moans and moves a hand down to my head.

“Right there…yes.”

She moans softly. I eventually stop writing with my tongue and just move it over, up, down, around and across her clit. Anything I could do to give her pleasure. She moans loudly and runs her fingers in my hair.

“Oh god.” Helen groaned.

I moan and double my efforts to pleasure her. She gasps at my effort and pushes my head farther into her sweet wetness. I moan again and softly suck her clit into my mouth. She moans loudly and arches her back.

“Holy mother of-“

She gasps as I suck a little harder and her fingers clench in my hair. I stop sucking her clit and lick her pussy rapidly. She moans again.

“Oh Liz…I’m almost there.”

I suck her clit again and she moans deeply.

“Just like that.”

I pull out and I begin to finger-fuck her, pushing one finger at a time into her pussy and shoving them in and out slowly and speeding up my speed. She moans really loud and I could feel her pussy pulsating around my fingers. I pull my fingers and watch as Helen breaths in and out quickly.

She lets her hands fall to the bed and I pull back and smile. I go back down on her and slowly flick my tongue over her clit. She shivers in pleasure and moans softly. I look up at her and move my hands to hers. I slide my hands in hers and she gasps slightly and looks down at me as I continue to flick her clit. My jaw starts to ache as I continue to pleasure her. She moans softly as my eyes meet hers. I whimper as she squeezes my hands lightly but encouragingly. I move my tongue faster and she moans loudly. Her breathing turns into panting gasps as she gets closer to her orgasm. She grips my hands tighter and breaks our stare and throws her head back. It was beautiful. Seeing her tremble and shake in orgasm. Her breathing halting momentarily in between each gasp and her thighs quivering against my cheeks. Her stomach muscles tightening in orgasm. She relaxes back onto the bed and her hands lesson their grip on mine. I slip my hands out of hers and move them to her legs. I run them softly over her thighs and kiss her skin lightly. She runs her fingers through my long hair and I look up at her. I kiss her thigh again while looking into her beautiful eyes.

“Your a natural sweetie. Nobody had ever made me cum like that. Holy fuck!” She said smiling, moaning and gasping for air.

Next, I lick my lips and move up on the bed towards her. My heart was pounding as I mounted on top of Helen’s body, leaned my face down while I look into her eyes, Catching her chin with my hand, I lean over and kissed her mouth. Immediately her lips parted and we went at each other with all the passion of the moment my tongue lashing against her teeth as I squeezed her breasts. I’ve been wanting to kiss her for the past 2 weeks, I wasn’t going to stop now. Our lips meet and she finally closes her eyes. I let out a small moan and kiss her again. She kisses me back and puts her hand on my hip. I moan again and kiss her harder. She moans and pulls me against her as she stands up straight. She reaches down and squeezes my ass making me moan and part my lips enough for her tongue to snake in my mouth. I maneuver my leg in between hers and move closer to her body. I was completely clothed and on top of this naked woman. I moan and kiss her harder. She presses her lips to mine. My eyes flutter closed and I moan. She moans as I kiss her back and tease my tongue across her lips. She slips her hands into mine and intertwines our fingers. I moan and melt into our kiss. She slides her tongue in between my lips and moans. Our tongues wrestle in our mouths as we kiss passionately. I moan and she kisses me one last time and pulls away but keeps her hands in mine. I wait a few seconds to open my eyes and look at her. I swallow as I realize that was the most passionate kiss I’ve ever experienced. Our eyes stare into each-other’s soul it seemed as I back my head away.

The next thing I recall is me kneeling in beside Helen’s face, undoing my top, bra, pantyhose, and pausing to stare at my bulging panties before impatiently grasping the sides and pulling them down, releasing my long stiff 6 inch cock! Helen seemed amazed and mumbled something about the size being even larger than she had ever imagined a trans would be. She held my big dick in her hands and slowly she lowered her warm mouth around my aching cock, sucking as she wrapped her arms around my body and cupped the cheeks of my ass, pulling me into her throat. I reached down and squeezed her breasts as she continued her avid sucking, thrusting my hips forward as I watched her suck me off. I could feel myself beginning to release pre-cum so I let go of her big saggy breasts and grabbed the back of her head, tangling my fingers in her curly blonde hair as I forced my cock deep into her throat. The pleasure was too much for me. I was about to reach the point of no return. I felt the tensing of my whole body, I shook as I came, shooting my load into Helen’s awaiting mouth.

Helen moaned, leaned up, opened her mouth and dribbled my seeds out of her mouth and rubbed my sperm onto her breasts and over her long nipples as I slowly pulled my prick out of her mouth. I pushed her back down until she was laying back on her elbows, her legs bent and her breasts sagging to either side of her body. “HOLY FUCK!” she yelled. I excitedly complied. I moved myself between her legs and took a look at the wonderful woman in front of me with a flabby stomach and plump thighs. Beautiful! Helen was completely naked in front of me, her grey haired cunt separated by swollen moist labia. Before she could object any further, I squeezed my head down between her thighs, my mouth resting against her damp bush.

I pushed my face back to her pussy; my tongue slid along her elongated lips.

Helen’s fingers clasped the back of my head as she pulled my face into her cunt, wrapping her legs around my body. “Ooooooh!” she cried as my tongue slid up to her pointed clit.

“Mmmm!” she sighed again as my hands cupped her saggy breasts and I began to suck and rotate my tongue around the sensitive bud. Helen’s hands pulled my head against her cunt with increased force as she lifted her hips and began to breathe in short rapid gasps, her impending orgasm taking over. Suddenly she began to cum, twisting and turning as her climax washed over her. Releasing one of her breasts, I slid my mouth down to her wet hole, probing into it with my tongue as I continued to manipulate her clit with my fingers.

Helen’s orgasm peeked and she sobbed out loud, tensing as she climaxed. Then, moving up her body, I licked at her nipples, pretending I was once again a child and she was my Mother; I nestled into her chest and suckled on her long teats. Eventually I moved over on top of her and as she opened her legs, my cock slid along her coarse pubic hair until it rested at the opening of her hot wet cunt.

“Fuck me!” she whispered “Fuck me Lizzie! Give me your cum! I want to feel your ladyboy dick!” Reaching down between us, Helen opened her labia and placed the head of my erect Viagra stuffed cock inside her. I began slowly thrusting into her, deep and hard, then faster and harder, until I thought that her cries would surely draw the attention of her neighbors.

Positioning my cock in and out of my Helen’s cunt, I squeezed her breasts and reaching down, pinched her long nipples as she lifted her hips and fucked me in return. We began to rapidly fuck one another for minutes on end, never stopping or breaking. My cock and balls smashing into the mother of two on end. The moans, the groans, we were both exceeding our limits and our bodies were hot!

“OHHHHH, OHHHHHH FUCK OHHHHHHHHHHHH!” she whispered urgently. Watching my friend Helen, her large breasts sagging towards the sides of her torso and her face tensed in ecstasy, I came, squirting my load deep into her open cunt as she milked my hard cock. As my hard cock shot it’s load deep into her body, Helen cried out “THAT WAS MOTHER FUCKING AWESOME!”

As I lay on top of her, the realization hit me that I had just fucked a female and although exhausted, I felt great! Helen also seemed to feel really good thanking me for how she was feeling. We kissed for a little bit before we laid down on the bed and cuddled with one another. This lasted a couple of minutes before Helen said she wanted to take a shower. We went to the washroom together where I sat down on the toilet and peed while Helen got ready to take a shower. I left for home when Helen entered the shower. We said we would try to do this again one day.

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