Was Melissa going to have sex with me? I couldn’t let myself believe it, but she seemed to be telling me that. There’s no way that she would have before, but maybe Kassandra convinced her to for some reason? I’m not sure why Kassandra would do that for me, especially after our… confrontational… meeting, but Melissa did say that while she had a special reward planned for me, Kassandra talked her into going further.
“Are you serious?” I asked.
“Take your clothes off,” was her answer.
I undressed in record time and stood in front of our bed, completely naked except for the locked caged around my penis.
“Do you think that I’m beautiful?”
“You’re one of the hottest women that I’ve ever seen Melissa.”
“Tayshaun thinks so too. He fucked me with a hunger that no other man ever has before. Do you want to fuck me Grey?”
“Yes, you know I do!”
“You want my pussy Grey? You want me to take off my clothes, take off that cage and let you slide your little penis into my sweet little puss?”
She was torturing me, my cage never felt tighter than it did in that moment. I whimpered “Melissa… you know…” was all I could get out.
Melissa laughed at my predicament, “How badly Grey? How desperately do you want it?”
“Sooo badly, Melissa. You know that I don’t want to be a virgin any more and you’re so gorgeous… plus, you know… I love you.” I tailed off.
“Do you think you could put your penis where Tayshaun’s giant cock has been? Do you think I’d feel it? He really stretched me out last night.”
Before I could answer, Melissa sat up on her knees and turned her back to me. “Come sit on the bed behind me Grey.”
I knelt behind her with my knees on either side of her body, while she was on her knees with her feet tucked in behind her.
She held her arms up in the air. “Take off my shirt.”
I hesitated for a moment, still wondering if Melissa was actually going to let me have sex with her but worried I was being set up for a disappointment. She did promise me something special. What could be more special than that? “Hurry” she insisted. I was as nervous as I was excited. I lifted her shirt off over her head and outstretched arms and tossed it on the floor beside us.
“And now my bra.”
I wasn’t going to fumble this up again, and focused on what I was doing. It wasn’t easy with my brain half-numb and my hands shaking but I popped the clasp and dropped her bra next to her shirt. Melissa let out a little giggle, “Much better this time!”
“Now, listen carefully. I want you to reach around and touch my tits. Be gentle, I don’t want grabby hands squeezing them, I want soft hands caressing them.”
I did as I was told, reaching around and taking each one of her tits into my hands, each one was a handful. She raised her own hands to my hands, guiding me and showing me exactly how she wanted to be touched. “Like this,” she said moving my hands beneath hers in a soft, circular motion. My penis was throbbing in its cage, uselessly trying to get fully erect. Fortunately, I was too distracted by what was happening to really notice how much it hurt.
Melissa tilted her head and pulled her hair to one side exposing her neck. “Give me soft kisses along here,” she said pointing to an area along her neck and shoulder. As I leaned forward to kiss her neck I was able to get a better look at her tits. I couldn’t believe that I was seeing my own hands gently kneading her tits and feeling Melissa’s body react to my touch.
“How are you doing?” Melissa asked as she reached behind herself and cupped my balls in her hand. It was the first time Melissa – or any woman – had ever touched me there other than the taps she gave me with her foot the day before. If wasn’t wearing the cage, I’m sure that her touch alone would have made me cum. As it was I was leaking a pool of pre-cum out of the end, causing a wet spot to form on the bed. Even without looking, I think Melissa could tell how hard my penis was, desperately trying to burst free from its enclosure.
Just as I was getting used to the feel of having Melissa's breasts in my hands, she pulled her own hand away from my balls, reached up and pulled my hands away from her tits. Before any disappointment could set it, she spun around and laid down on the bed with her arms crossed above her head. Her new position put her magnificent breasts on full display, the key to my chastity cage on a necklace nestled between them. Her nipples were erect and perked up noticeably.
“Kiss me here,” she said pointing to her right nipple. I laid down beside her and moved my head over her exposed breast. I started by giving her nipple soft kisses, then held her breast in place with my hand as I took her nipple in between my lips and started sucking it gently. Melissa moaned and said “Don’t forget about the other one” as she raise her left side and leaned towards my mouth to give me better access.
For what seemed like ages, Melissa looked down at me smiling, watching as my lips moved from nipple to nipple as I became more comfortable and more confident with what I was doing. This was incredible! As excited as I was, I couldn’t fully enjoy myself. The whole time that I was focussed on Melissa’s tits, I couldn’t avoid seeing my chastity key laying on her chest right in front of my face. It was a constant reminder of the pain I was now feeling in my balls. At one point I moved the key out of view as if it was in my way. I pushed it and let it slide down on her necklace until it flopped down beside her neck and onto the bed, but Melissa immediately moved it back into place. She knew what she was doing, and it was very much with full intention.
Melissa stopped me by pushing my head away from her chest, instinctively I pushed back not wanting to stop but she held her arm firm.
“Take off my pants.”
Again I couldn’t believe what I was hearing. I didn’t know where Melissa was going to take this, but I never would have even allowed myself to imagine that I’d be in bed with her, already half naked and now being told to take her pants off. I was really starting to believe that maybe Melissa was going to take my virginity. After all, this started with her telling me that Kassandra talked her into doing something even more special than what she’d already promised me and by asking how badly I wanted to fuck her. Maybe my desperation was convincing. I undid her pants with trembling hands that Melissa noticed. She lifted her hips off the bed as I slid her pants down, fulling removing them. She motioned for me to pull her socks off too, which I did. The sight before me is one that I will never forget as long as I live. Other than her black silk panties and a necklace holding my chastity key, this absolutely stunning woman who I had been in love with for years was naked before me.
Melissa could see how awestruck I was and she knew that she had me. As if there was ever any doubt.
“Kiss my toes,” she instructed. I wasn’t really into feet, but in that moment I would have done anything that she said. I held her foot up to my face, rubbing it gently and began giving it light kisses, starting near her heel and working my way to her arch, I transitioned to the bottom of her foot as I kissed my way up to her toes. I gave each toe a series of kisses before taking her big toe into my mouth and sucked it.
Melissa was laughing as much as she was smiling. I don’t know if she was enjoying what I was doing but she clearly loved the power and control she had over me. I was trying to maintain eye contact with her, but I couldn’t help but drift my gaze down to her panties and what was hidden beneath.
“Come here,” she said as she spread her legs and motioned for me to position myself between them. As I leaned in, she pointed to a spot on her flat stomach. “Kiss me here.”
I gave her kiss after kiss all over her stomach and she looked down on me. “A little lower,” she said as I worked my way down to her bellybutton. After a brief minute of kissing, “A little lower,” she said again. I was now kissing the area where the top band of her panties met skin. She spread her legs wide open for me. “Kiss me here,” she said pointing to the inside of her thigh.
As I moved myself lower to kiss her thigh, I became eye level with her panty covered pussy. I could see a wet spot forming on the crotch of her panties and could smell the musty odour that I loved so much when I masturbated with her panties. I tried to focus on kissing her thigh, but my eyes were fixated on her panties and the pussy they covered.
“Grey,” Melissa broke my trance. “I want to give you a choice.” She sat up quickly, pulling herself away from me. My face dropped as it was impossible to hide my disappointment. I was sure this was going to be the let-down that I feared. We were on our knees, facing each other eye to eye. She placed her left hand on my shoulder and held the back of my neck as she reached down with her right hand once again cupping my balls. For the first time, I looked down and saw the state that I was in. My penis was as hard as it could be, still trapped in chastity it stuck out from my body as much as possible. My balls were a shocking colour, a deep red on the verge of turning purple. I suddenly became aware of exactly how much pain I was in as Melissa’s soft hand felt like sandpaper on my sensitive and stretched out balls. I winced and pulled away from her reactively, but she had no intention of letting me escape. “Don’t pull away.” It was more of a command than a request.
“Now, here’s your choice… hold your hand out.” I did, and once extended she pulled my key off from around her neck and placed it in my hand.
“If you really think that you need to cum, unlock yourself and stroke that little penis for me. Understand though that things are just starting to get hot and that would be a disappointment to me, but if you need to cum and want to end our play time you can go ahead and stroke it. Or…” she paused to increase the tension. “Give the key back to me, and you can take my panties off and we can keep playing.”
My head was in a total fog. I’ve never needed to cum more badly than I did in that moment, but Melissa was offering me something more – maybe my false hope was really good faith. I had a million questions, but I couldn’t get any of them out in the moment. I just stared at Melissa with what was probably a blank look on my face. She could tell I was struggling to make sense of everything that had just happened and what might happen next. Still rubbing my tender balls, Melissa smiled back at me with an eager and encouraging expression, making it very obvious what she wanted.
Probably getting impatient waiting for me to make up my mind, Melissa leaned in close to me and whispered in my ear “You’ve made my pussy wet Grey, come on and finish what you started.”
That made my mind up for me. I put my key back around her neck as Melissa’s face lit up happy with the decision that I’d made. She laid back down and lifted her hips off the bed and waited for me. “It’s all yours.”
I reached down to remove her panties, practically mesmerized. I grabbed them from either side of her hips and began to pull them down. She moved her hands to stop me.
“You know you’re not going to fuck me right?”
It was crushing to hear because I was so full of hope. Still though, I was taking her panties off and she’d promised something special. This had to be leading somewhere. Maybe she was just teasing me and would let me fuck her.
“This pussy is for big cocks only, no little ones allowed. Now might be the time to tell you that one Kassandra’s ideas is that I should only fuck black guys from now on. I think that’s a good idea, don’t you?”
“I guess so.”
In the moment I didn’t care about who fucked her realizing that it wasn’t going to be me. I just needed to see her pussy. I guessed she was going to let me stare at her nakedness as I masturbated for her. She let go of my hands and let me continue to take her panties off. She kept her legs together as I took her panties off. Instinctively as soon as they were off I held them up to my face and inhaled her scent. As I did, she spread her legs wide open for me giving me a clear view. I was mesmerized.
She tapped the inside of her thigh, “Kisses.”
I put her panties down on the bed and moved back into the position that I was in earlier, kissing the inside of her thigh and staring at her – now fully exposed – pussy. I’d seen her naked the day before when I helped her bathe, but that was nothing like what was happening now.
Melissa pointed to spot higher up on her thigh “Closer,” and I moved my way up. Melissa moaned, sighed and then bit her lip. It was the first clear evidence that she was really liking what I was doing. “Here,” she said now pointing to her opposite thigh. “Kiss your way up.” I repositioned myself and did exactly what she said. Starting at the midpoint of her thigh I kissed and licked my way up the inside of her leg, the whole time my eyes locked on Melissa’s pussy. She reached her hand down and spread her lips open to give me a full view. I’d been thinking about and lusting after her pussy for years, and there it was right in front of me, spread open. Melissa’s chest heaved as I worked my way up her thigh and inched my way closer to her pussy. She was breathing heavier now, leaving no doubt that she was enjoying herself.
“Kiss around my pussy Grey. Don’t touch it, just kiss close to it. Softly”
I did what she told me to do. I wanted to taste her so badly that my mouth was watering. Her breathing had picked up even more, and her whole body was reacting to my lips and tongue.
“Listen carefully. I want you to lick my pussy. Long licks. Start at the bottom and go up, use the flat of your tongue.” Melissa was panting now, having problems speaking in full sentences.
I followed her instructions and gave her pussy nice, long licks. I didn’t really know what I was doing so I improvised, changing pressure, sometimes licking hard and other times just brushing my tongue against the inside of her pussy lips. I let her reaction guide me. Having seen it done in porn movies, I licked my fingers and slid them inside of her, first one and when she didn’t reject it, then a second one. As my moved my fingers in and out of her I focused my kissing and licking towards the top of her pussy where I thought her clit was. She didn’t stop me, so I kept going at it and Melissa was starting to lose control. I was trying to imagine what it would feel like to have my penis inside of her, to be on top of her and fuck her…what it would be like if I had a proper cock and used it to make her make her moan like she was from my tongue and fingers. Her legs were thrashing about, and I had to use one hand to keep her legs spread to stop her knees from hitting me in the head as I kept working away on her pussy.
“I’m cumming, I’m cumming, Oh my God I’m cumming! Don’t stop, keep licking!”
She was sitting up now, looking down at me she put her hands on the back of my head forcing my face into her pussy. She was fucking my face as much as I was licking her at this point. She was moaning and making noises that I’d only heard her make with a very few guys. Normally, I’d be in my room beating off right about now but this time I was in bed with Melissa.
“Holy fuck!” she yelled as she pulled her leg up, put her foot on my shoulder and pushed me away from her, and immediately flopped down on the bed trying to catch her breath.
“Holy shit Grey, you made me cum.” She was in disbelief. So was I.
My penis was aching worse than it ever had. With my head out of its fog, I suddenly became re-aware of all the pain and frustration in my balls – my penis desperately hard with a near constant dribble of pre-cum leaking out.
“Melissa, my…”
She cut me off, “Shhhh! Let me enjoy this.” She laid there for a few more minutes, slowly regaining both her breath and her composure. Her legs were still spread wide open in front of me, teasing my locked up penis which was still dripping like a leaky faucet.
After a few minutes, Melissa sat up, her face recovered to her normal expression – albeit with a giant smile now.
“I can’t believe you just did that Grey, you’re a natural pussy licker!”
I was in too much pain to be proud, “My penis… I need out. Please!” I could barely speak.
“Right, ok”.
She pulled my key from off around her neck as she got up on her knees in front of me. As she reached down to hold my penis in place, she pointed to the leaky mess that I’d made on the bed.
“Wow, it looks like your chastity tears cried themselves a lake!”
“Melissa, please! I’m in pain here I need to get out of this thing!”
“Calm down, it’ll be off in a minute.”
Even this small delay was absolute torture, each second felt like an hour.
She reached down, cupped my ball her hand and began to slide the key into the lock.