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Friend was the worst word in the dictionary.
He didn’t reply, and I felt sad about it. I needed to stop, because thinking about him only made my life harder.
I pushed myself to pull up at those gates, and second guessed my decision even more as I walked inside of the front door.
The only thing that kept me motivated was the idea of providing for my kids. I’d do anything for them, and nothing was going to stop me, not even my conscience.
Session #1
“Close your eyes, Lily.” I did as I was told, allowing Ms. Cybil to put the blindfold over my eyes. I could feel my legs shaking under the long robe as my view was being disturbed by the thin silk fabric of the mask. Then the robe, that was given to me after she had me strip nude, was removed.
One at a time she grabbed my hands and put them behind my back, wrapping them in a scarf.
It was bad enough that she’d made me strip in front of her, also part of the session. Apparently I’d have to be comfortable being naked in front of my client.
Duh!
How I thought that any of this was going to be doable was beyond me. It was clearly the worst decision I’d made to date. “I’m afraid,” I admitted out loud. Sure, I’d gone along with this because it was for the kids. The idea of being naked around a strange man was preventing me from being able to remain calm.
What was I doing?
How could I let a stranger touch me?
What if I ran out of the house naked and drove home?
This was the worst decision of my life, aside from trusting Mr. Shit Stains.
She stood over me, coaxing the fear away, by assuring me that if I just let go I’d be able to experience something new and exciting. I had to take it for what it was.
Just sex.
After Ms. Cybil had spoke to me a few more moments I’d been able to agree to opening up and allow the session to give me the opportunity to try a few things without crossing any boundaries. She needed to know if I was going to be able to let myself become the woman she expected. I still wasn’t sure, but had agreed to one hour.
I just had to get through two sessions. Just two. The problem was that I had no details on either of them.
My first training session was under the watch of Ms. Cybil. I knew she’d be judging me, so I made sure I shaved all of the hair off of my body, and wore the sweetest smelling lotions. I didn’t have the energy to hear that I wasn’t good enough. After what I was going through I needed to hear something positive.
I knew it was just the two of us, and after all of the questions she’d answered I should have felt more comfortable. She’d assured me that this was for my own experience. I had to trust that she knew what she was doing, after having given so many other women and men a chance to change their lives.
A quick tug assured that my hands were secured behind my back, and I heard her heels clanking away from where I was seated. After a door shut, the room had become quiet. I sat there, not able to see anything or know what was going to happen. The door opened again, and as Ms. Cybil had requested I stayed still. I never heard high heels, or the sound of feet walking across the hard floor.
As my lips parted to ask if I was alone I felt someone touching me.
Oh my god this is really happening.
Soft fingers glided over the skin on my shoulders, followed by the person’s breath on my ear. It was enough to give me chills down both of my arms. I could feel the two hands traveling down the front of my collar bone. They traced the skin above my breasts and my nipples instantly got hard as the fingers trailed closer. They circled around the areolas, never touching my hardening tips. I’d never been touched by a woman, and didn’t know the sex of the person touching me, but I was almost sure it was a female.
Holy shit! I was not a lesbian. I didn’t agree to becoming one.
Oh my…It felt so good.
The assumption brought a surprising excitement over me. I hadn’t thought about it before, but there was something so sultry about a woman gently caressing another woman.
What had I gotten myself into?
I attempted to shuffle around, to maybe wiggle out of my blindfold and restraints, just to be able to come to grips with what was happening to my senses. I was then caught off guard when a familiar voice filled the room, from far away. “Stay still, Lily. Accept what you’re feeling. Free your mind of what you think is happening, and grasp what your body is telling you instead.” Ms. Cybil wasn’t anywhere near me, which only made me more curious as to who was touching me. The idea of it being a complete stranger made it both frightening and exciting at the same time.
Warm, wet lips rolled over one of my nipples. I bit down on my own as I felt and heard suction being applied, first with ease and then more forceful. I sensed warm air being blown on it, right after the lips were removed. Chills traveled down my leg, but I remained as still as possible.
I could hear her breathing, and tiny sounds escaping her as she played her role.
For someone that was petrified of this, I had to silently admit to myself that I was enjoying it, probably more than I was supposed to.
Fingernails glided over the skin directly under my breast, down across my abdomen. The contact made my nipples harden more, heightening the sensations in them once again. I gasped, almost moaning out loud, from just one sort of touch. My heart was racing, and I licked over my lips, wanting, no waiting, for what was to come.
When the fingernails stopped, I knew they were at the base of my pussy. I felt them leave, only to start again on my inner thighs. As they moved I could feel my legs being pushed apart, spread open as far as I could go. My pussy was exposed, and I couldn’t think of anything else than being touched there, in my most personal area.
I couldn’t stop licking my lips, and trying to keep still, while I knew that all of this was happening while Ms. Cybil watched us.
Being blindfolded made for a different type of experience. The not knowing took me to new heights and I’d yet to have been touched there.
Then, as soon as I felt those gentle hands playing with either side of my folds, someone placed a strong hold on my shoulders. Those hands started moving down over my breasts. I leaned back in the chair as I felt myself being stroked so tenderly by these two strangers. On one hand, I wanted to jump up and run out of there because I knew what I was doing was wrong. On the other, I had to admit that it felt so good. I could feel hot breath before lips touched mine. The kiss was full of tongue and the whiskers rubbing over my cheeks let me know that at least one of the participants was a man. His kisses weren’t aggressive like Charlie’s usually were, and they certainly weren’t like Eli’s. This man kissed me slowly, passionately, as if we had all of the time in the world. He kissed me like we were all alone, and his intent was to please only me.
Just as fast as it started he pulled away and turned my head to the side. His lips traced the nape of my neck, while someone else began rubbing my clit. I bucked in my seat, unable to comprehend the fact that I was going through with this and enjoying it when I’d promised myself that I wouldn’t. The harder they rubbed the more my body responded, almost unable to sit there without shaking.
My first orgasm came quickly and the room got quiet.
I couldn’t hear either of the people around me, and without being able to free my hands and lift the blindfold, I wasn’t sure what was going to happen.
“Did it feel good, Lily?” Ms. Cybil’s voice filled the room again.
I nodded, unable to admit it out loud.
“That was just the beginning, love. Catch your breath and prepare to be satisfied beyond your belief.”
Her words, so scary yet so exciting, only heightened my experience more. I’d already climaxed and she was telling me that something even better was going to happen.
I could hear the vibration of something and it was getting closer. Suddenly my hands were being untied from behind the chair. Instinctively I reached up to remove my blindfold, but was grabbed before I could
get to it.
“The blindfold stays on until I know you’re ready, Lily.”
It scared me a little, hearing her tell me that. Hadn’t she seen that I’d enjoyed what happened just moments ago? Wasn’t being tied up and watched enough torture for one day?
I felt my hand being grabbed and was suddenly lifted off of the chair. The person walked behind me, holding me by the wrist and guiding me over to where there was something cushiony. At first I thought it was a bed, but it was so large that I wasn’t quite certain. Had I’d been more prepared I would have taken in my surroundings before being blindfolded.
My body leaned over the soft padding, leaving my ass up in the air. The person behind me rubbed on my ass cheeks, while the object I was leaning on had began to move, like someone had climbed on the other side and was approaching me. I could hear the vibrating getting closer, but didn’t anticipate someone’s lips to smack against mine. This was different than the ones before it. The tongue was smaller and it moved in different directions. The lips were wet, and I tasted fruit as if it were lip gloss. Realizing that there were no stubbles, I pulled away shocked that I was possibly kissing another woman for the first time, which was something I never in a million years thought I’d be doing.
Whoever it was grabbed my hair and pulled me toward them again. “Don’t fight it.” The shockingly female voice whispered in my ear.
My heart felt as if it was beating out of my chest again and the reality of what was happening had finally smacked me right in the face.
I was having a lesbian encounter with a woman.
Then I felt something hard pressing on my ass. I shot up and arms wrapped around the front of me, holding me in place. The female approached again, grabbing at my cheeks and pulling me into another kiss. I started to pull away, but she held my face there, and tried again.
Underneath the blindfold I wanted to cry. This was all so wrong and frightening to me. I know I’d enjoyed it before. There was no denying what they’d all seen for themselves, but somehow knowing what I knew now made me rethink those feelings. Imagining that I was going through with this, while my children were at home, so innocent, made me want to crawl in a ball and die. They’d never forgive me for this, and I didn’t know if I could live with that.
While feeling the obvious erection behind me, and being kissed by some unknown woman, I felt the vibration of something touching me. It was some kind of dildo, or wand that was being pressed on the base of my sex. Immediately I lost my train of thought. The intensity of the situation was overwhelming me so much that I couldn’t rationally think.
The woman kissed me again, this time biting on my bottom lip and pulling it with her teeth. A tiny moan escaped her lips and I lost all control. I don’t know what made me do it, but I lifted my arms up and touched her intentionally. I felt her slender waist and traveled up until I felt the underneath of her naked breasts. Her smooth skin felt so cared for as my palms glided over it. Her lips met mine again, and suddenly we were being pulled down, with me on top of her. With a little shuffle I heard her gasp, and then felt the person behind us slapping himself into me. I think I hadn’t considered our position and what could be happening until I heard the sounds of them both responding to each other.
He was fucking her while still standing, while I laid on top of her naked body. His hands played with my ass as he worked his pace. She held me tight, while kissing me again. All I could think about was being thankful that I’d shaved every appendage. The idea of a stranger knowing what my asshole looked like was appalling.
Then, just as fast as it had begun, it stopped. His hands were on my ass and I felt his erection, still so hard, slapping over my cheeks. I pulled away from the woman’s lips, but she held me there, close. “We’re here to please you, Lily. Don’t be afraid. This is all for you.”
She kissed me one last time and started sliding up. I lifted my upper body on my elbows, determined that I wasn’t going to be face down in her pussy. At the same time that we were wriggling around, a large, stiff cock, was now positioned at the base of my sex. A hand came around and started rubbing the top of my pussy. I clung to the sheets unable to grasp how my body and mind weren’t in the same place. Finally I heard his voice. “Do you want me to stop, or do you want to cum?”
When I didn’t answer, I heard giggling. “She wants to cum again.”
Ms. Cybil had said no penetration, but clearly this guy was ready and willing.
The female was answering for me, as if she could read my deepest desires.
Then I heard a few voices coming from far away. “What’s going on?”
The female answered. “Nothing for you to worry about. Stay focused. It’s all part of the session.”
I had no reason not to believe her.
I heard the door open and close but nothing changed. The man’s hands were on my ass again after about a minute of him being unresponsive. Maybe he had to get the go-ahead to proceed with intercourse, or maybe it was my last chance to tell him to fuck-off, which I couldn’t bring myself to do. I was too turned on, too lost in the moment, too hungry to be satisfied.
He entered me, not slow and careful, but with force and enthusiasm. I cried out and fell on top of the woman’s abdomen. Her fingers massaged my scalp as my body lifted with each thrust. Then she began moving erotically beneath me. I knew her pussy was inches below my chin, and as afraid as I was to be considered a lesbian, I found myself wanting to touch her the same way she’d touched me. With no regard for the regret I’d feel when it was all over, I let my hand travel down her stomach. She was shaved and just as smooth as the skin I’d touched before. I let my fingers trace over her smooth folds. She bucked her body, accepting my touch, and allowing me to continue. “That’s it, Lily. Just go with it.”
Meanwhile, I’m giving into temptation, and being fucked from behind, by some stranger that I’d never even laid eyes on before. How did I get to this point? As he rubbed over my sweet spot vigorously, I started doing the same to the female. She groaned and accepted my touch, turning me on more than I could ever remember being in my whole life. The excitement was just too much to handle. My body began to let go, and I came, which only made him fuck me harder.
Where I thought I was spent, he was showing me that my orgasm was still going, taking me to new heights. I never let my fingers stop rubbing on the female, and soon she was crying out. Just a moment later and he, too, was definitively at the end of his rope. I’d made another woman orgasm, and waves of pleasure washed over me, until finally my own body collapsed over her spent body.
I felt him pulling out of me, leaving me vulnerable and exposed, but I never moved. Soon, the female was pulling me up into her arms. Our lips met and she laughed against me. “Are you ready to take off the blindfold?”
As nervous as I was, I wanted to see who’d I’d just been with. I needed to know whether I saw them at the grocery store, or maybe they were parents like me.
I nodded.
“Are you sure, you’re ready?”
I licked my lips. “Yes.”
“You can take off the blindfold, under one condition.”
“Anything.” Though I wasn’t sure how much more I could take.
“Tell me how much you liked it, Lily? Admit to me that you could let yourself enjoy it. I know you did.” She reached down and slid her fingers between my spent folds.
I let out a whimper, unable to hide my emotions. “I did.”
“You’re so wet. I bet you taste fantastic. Smelling your pussy is making me so hot again.” She shoved her fingers inside of me, at least two of them. “Let’s take a shower together. What do you say?”
I couldn’t say much while she was steady fingering me, gliding her thumb over my swollen clit. I started trembling, as if I was going to lose control at any minute. The idea of showering with a woman, kissing her, and touching her pussy was too much for me to handle. I cried out again, hearing my voice echo in the room.
When the woman removed the blindfold
I looked around the room to see that we were alone. There was no man present, and neither was Ms. Cybil. While I turned to face a beautiful exotic looking brunette, I was taken aback by what we’d just done together. “Where is everyone?”
“The session ended.”
I covered my body with my hands, even though she’d seen all of me. “What does that mean?”
“It means you’re done for the day.” She traced her fingertips over my arm, and I wanted to pull away, but I couldn’t. I found myself wanting to kiss her with my eyes open. “Did I make you feel good?”
How could I lie when she already knew the answer. “Yes.” My face blushed with the admission.
“Just because you experienced a woman doesn’t mean you’re gay, Lily. You opened your body up to being satisfied. People have been doing it since the beginning of time.”
“I just had sex with two people at the same time. I had a threesome. I should feel terrible.” Oh my God, I was seriously going to Hell. I’d just decided my fate. That damn demon on my shoulder won again.
Just before she could respond we heard yelling coming from another room. I couldn’t make out all that they were saying, but Ms. Cybil clearly said, “I told you no penetration. This was a terrible idea. Get out of my face before I say something I’ll regret. Frankie, you had no business barging in.”
The exotic woman began to laugh. “I had intercourse during my first session. Did you ask for no penetration?”
I shrugged. “She told me that there wouldn’t be any.”
“Your client must want you as innocent as possible.”
“My client? You mean she’s already got someone lined up?” Knowing that made me feel like I hadn’t just had sex with two strangers, I was also about to have sex with someone else. “I can’t believe that I just did that. I’ve never done something so -.”
“Hot? Reckless? Exciting?”
“Yeah.”
“I think everyone’s first sessions are like that. We want to think that we won’t be able to go through with it, but somehow each of us comes out feeling like it was the hottest sex we’ve ever had. I’ve only heard of one person not being able to go through with it. Ms. Cybil is very thorough. I’m sure she’s got plenty of men on a waiting list.” She stood up in all of her nakedness in front of me. “How about that shower?” I watched her bite down on her lip as she waited for my reply. A fire between my legs ignited when my eyes passed over her hard nipples. I was dripping with desire to be touched one more time by a woman with my eyes open. Whatever was going on in the next room wasn’t my concern.