Becoming a Cuckold
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Becoming Melissa's Cuckold Pt. 08 free porn video
The two days following my first sexual experience with Melissa were amazing. I felt closer to her than I ever had before and just as importantly it felt like she was just as close to me. For those two days, it felt like a normal relationship, one in which we were both in love. We were at each other’s sides the whole time, held hands when we went out, snuggled up together when we were at home and she looked at me with a softness in her eyes that I’d never seen before. When I look back on my relationship with Melissa, these two days are often the first thing that comes to my mind. I didn’t know it then, but it was the calm before the storm.
Wednesday rolled around and Melissa and I had a meeting with Diane, the relationship expert who’d helped us along the path that we were now on. We knew her socially, so while we were going to her place that evening for a therapy session, it was more informal. Diane had told us that she was free for the whole evening and that we could drop by any time after dinner.
When I got home from work, Melissa was just stepping out of the shower.
“Perfect timing, you can help me get dressed,” was Melissa’s greeting.
I dropped my things by the front door and immediately walked with Melissa into our room.
“I loved the way you dressed me the other night for Tayshaun. Why don’t we do that again?”
“You want to get dressed up like that for Diane?”
“No, not exactly – but I do want you to pick out an outfit for me to wear tonight. Nothing too slutty, I want to be presentable for Diane, but I also want to look sexy. Dress me how you’d want to see me if you were going to introduce me to your parents… and then fuck me afterwards.”
I figured that Melissa wanted to show Diane how she was ‘training’ me as she put it, maybe showing off the success that she was having with me. I wasn’t going to disappoint her. Melissa sat on our bed quietly while I went through her wardrobe looking for the perfect outfit for her to wear. I was still pretty clueless when it came to fashion, but I’d seen Melissa wear so many different things that I had an idea of what she liked to wear in certain situations and I definitely knew what I liked to see her in.
I picked out what could pass for office-wear, but with a sexy edge to it – maybe something that you’d see a naughty secretary wear in a porno movie. I found a tight fitting white sweater that showed off her best curves. The cut of the neck was low enough to walk the line between office appropriate and outright putting her tits, which filled-out her sweater nicely, on display. Just the right thing to start the office tease look that I was going for. Next was a black suede skirt with thin white stripes. It was long enough to be stylishly classy, but tight enough around her waist and thighs to frame her ass in the most tempting way imaginable. My first inclination was for her to wear black nylons, but Melissa made me realize that with a longer skirt she could wear garters and stockings. That gave the outward appearance of being presentable, while still having that sexy underneath requirement that she wanted. With that done, it was just a matter of picking out the right shoes. I found some heels that I’d always liked, a pair of black high-heeled shoes that definitely pushed the limits of common acceptability but added another element of sexiness that Melissa was looking for.
“How should I wear my hair?”
“Well, we’re kind of going for that naughty secretary or sexy librarian look, so I’d tie it back and put it up in a bun. Maybe wear your glasses instead of you contacts?”
“Both great ideas,” she said as she thanked me with a kiss on the cheek.
She topped her look off by picking out a pair of earrings and a few other accent pieces, my chastity key on a necklace around her neck front and centre. Clearly Melissa was excited to show Diane that she’d won our battle and had convince me to buy and wear the chastity device that Diane had recommended that we experiment with.
I was proud of how she looked and loved being seen out in the public arm in arm with Melissa, especially when she was dolled up like this. It was such a boost to my confidence when I noticed other men looking at me with envy. If they only knew!
With Melissa looking her best, I had to get myself ready. I took a quick shower and got myself dressed. We still had some time to kill before leaving for Diane’s, if we left then we’d have been at her place by six, which might be cutting it close to her ‘any time after dinner’ invitation.
Our apartment had been converted from what used to be a store and we had a large street-level storefront window that was about three feet off the ground which allowed curious people walking down the sidewalk to look in on our foyer. In the foyer, there was a bench built along the wall beneath the window, so that anyone who sat there you could be seen from about the middle of their back up to their head by passers-by. It was more of an oddity than an invasion of privacy as there was a door that separated our foyer from the rest of our apartment. We weren’t really bothered if someone wanted peek in and see where we hung our coats. Still though, it was a sizeable room and we occasionally sat on that bench to have our morning coffees as the rising sun warmed our backs.
We sat on that bench talking, biding our time for a while delaying our drive to Diane’s to make sure that we didn’t impose on her dinner time.
“Why this outfit Grey?”
“What do you mean?”
“Out of all of my clothes, why did you choose this outfit?”
“I thought that’s what you were looking for?”
“Well yes, it is, but a lot of outfits would have served the purpose that I wanted. Why this one? If you were going to introduce me to your parents and fuck me afterwards, this is what you’d want me to wear?”
“Yeah, I guess so. Maybe I’d tone it down a bit for my mum, but my dad would sure love it!”
Melissa smiled. “And then to fuck me afterwards, what I’m wearing underneath would turn you on?”
“Yeah, for sure.” Of course it would, but Melissa made it so clear so often that she wasn’t going to have sex with me and it only hurt my locked up dick to think about it.
“Take your pants off.”
“What?”
“You heard me.”
“Melissa, people can see us in here and we need to get going soon.”
“Off. Now.”
I wasn’t sure what she was getting at here, but the sternness in her voice made me realize that I’d better listen. The sidewalk wasn’t busy outside and I hoped that anyone passing by would be too focused on racing home after work to peer into our foyer. I got up, undid my pants and took them off.
“Fold them and place them on the bench.”
I did as I was told.
“Underwear too.”
I was nervous and reluctant to be naked from the waist down in possible view from the sidewalk but I could tell that Melissa wasn’t going to take no for an answer. It would be easier for me to just do it, rather than trying to argue with her and end up doing it anyway. That type of corrective thinking was the power of chastity in action.
Melissa stood up, lifted her skirt above her waist and sat back down. She raised one leg and placed in on the bench, leaving the other one grounded on the floor. Her stockinged legs and panty covered pussy were on full display to me.
“On your knees.”
“Melissa, there are people walking by.”
“Don’t worry about them, worry about me. Get down on your knees.”
Again, I followed her instructions.
“You did well the other day. I want to know if it was beginner’s luck or if you really do have a natural talent for eating pussy. Come,” she said motioning me with her finger.
This unexpected turn of events combined with the thrill of perhaps being seen had me instantly throbbing in my chastity device. I leaned in and began kissing and licking the inner part of Melissa’s thigh, alternating between each leg just as I’d done for the first time a few days ago. After a few short moments, Melissa used one hand to pull her panties to the side and placed the other on the back of my head directing me towards her pussy. “We don’t have all day,” she said looking down at me with a smile.
I did everything that I could remember from the day before, starting by using the flat of my tongue and giving her nice long licks. She let out a moan letting me know that I was on the right track. I moved my hands to her thighs and spread her legs further apart, her hand on still my head directing me as I darted my tongue in and out of her pussy, alternating with licks. Melissa’s breathing picked up and I could tell that she was enjoying herself. I licked my fingers to insert them into her, but she swatted my hand away. “No, just your tongue,” she panted out as I went back to my lapping motion. Melissa was very wet at this point, and her pussy lips curled and opened – blooming like a flower right in front of me. She pulled one of my hands that was holding her legs open and had me hold her panties to the side as she used her fingers to pull back the hood of her clitoris, exposing it in the process. “Lick my clit,” she managed to get out while gasping for air. I focused my attention on her clit, first giving it little kisses before licking it and finally taking it in between my lips and gently sucking it. “That’s it baby, suck my clit… don’t stop… keep sucking…” she tailed off as her hand pushed my head harder into her pussy as her own head shot back in ecstasy. She was moaning loudly grinding her pussy into my face as my mouth struggled to keep up with the movement of her hips. Finally Melissa’s body tensed up and I could tell that she was cumming. I don’t think that she realized it, but Melissa was repeatedly knocking her head on our window drawing attention to what we were doing. It’s doubtful that anyone could have actually seen anything, but anyone watching would have quickly figured out what was going on.
After what seemed like a long and drawn out orgasm, Melissa finally release my head allowing me to sit up. I hadn’t realized it, but my knees had become sore from kneeling on the hard floors.
“Wow, Sunday wasn’t a fluke. You’re really good with your tongue. I’ll have to thank Kassandra for the suggestion. I think you’re going to work out just fine as my oral-slave cuck.”
“Slave?”
“Just an expression. Nothing to worry about.” Melissa looked down and saw the state that she was in.
“My panties are all wet, I can’t go out like this. I have another pair that are just like these ones. Bring them to me,” she said as she stood up and slid her panties off waiting for me to return with a fresh pair.
There was an immediacy to the tone in Melissa’s voice that made me think that taking the time to put my pants back on would have angered her. Being naked from the waist down, I was nervous about leaving and coming back to the foyer. The further away from the window that I got the better the viewing angle was from outside, and anyone’s attention that had been drawn by Melissa tapping her head on the window would surely still be watching. I hoped for the best as I dashed off to our bedroom and found the panties that Melissa wanted and carefully timed my run back to the foyer waiting for a lull in the sidewalk traffic.
I could tell by the look on her face that Melissa loved the sight of me running around, nervous and naked, while I held my chastity device in place – in part to hide it from being seen if anyone happened to look into our foyer and also to stop it from flopping around as I ran. As she put her panties on and straightened herself up, I stood before her still partially naked.
“Let’s have a look,” she said as she held me by my chastity device and sat down on the bench in front of me while I stood. “Hmm…I see a little bit of leaking, but you obviously aren’t as desperate to cum today as you were the other day. Even though you’ve earned it, I don’t think you need a hand job today.”
As much as I wanted it, I was really worried that if I pushed for it she’d do it right where we were – me standing, looking out the window with Melissa sat directly in front of me it would have been impossible to hide what was happening. I also had to admit to myself that what she was saying was true. I really wanted to cum, but didn’t need it like I did the other day. I was slightly worried about what that might mean though. Was I getting so used to being in chastity and not cumming that I no longer expected to cum when I was aroused? I’d just gotten my first handjob a few days ago, I’d cum harder than I ever had before from it, and here I was just a few days later oddly relieved that I wouldn’t be getting another one.
“Besides,” she added, “you should probably get your pants on and we should get going. Diane will be waiting for us now.”
We drove out to the suburbs where Diane lived, and arrived around 7pm. Diane greeted us at the door and welcomed us inside, sitting us down in her living room instead of her office. She explained that her husband was out of town and we’d have the house to ourselves so our meeting could take place in the comfort of her living room. When she mentioned her husband, I had a sudden flash of realization.
We originally met Diane because she was dating Philip, a black guy who we shared some common friends with and who occasionally hung out with us. Diane just mentioned her husband and I knew for sure that she wasn’t married to Philip… she must have been into this whole cuckolding thing too!
I was still trying to figure out if there was anything else that I’d missed as Melissa and Diane got caught up on some small talk as Diane brought us some drinks - a glass of wine for Melissa and beer for me. Clearly this was going to be less formal than our first session with Diane.
“So,” Diane eventually dove in, “how have things gone since our last meeting?”
Melissa perked up, “It’s been amazing! I’d say that you saved our relationship, but really you gave us a relationship! Before talking to you I couldn’t ever see myself with Grey, but now I can’t really see myself without him.”
There was a backhanded compliment in there somewhere, and I chose to focus on the good part.
“We went to the sex shop that you mention, Grey bought himself a chastity device and it’s changed everything for us. We owe you so much! Well, you and Kassandra.”
“Ah, Kassandra,” Diane said knowingly, “I had a feeling you two would hit it off.”
“You know her?” I asked.
“Yes, of course. I didn’t just send you off to some random shop. I sent you to a place where I knew that you’d get help. Our community isn’t a very big one, and a lot of us who are active in it tend to know each other.”
The gears were slowly grinding in my head. If Diane knew Kassandra, and Melissa had told Kassandra everything, how much did Diane already know and more troubling for me was how much did Philip know?
Melissa was looking at me, I think realizing that I was piecing it altogether. “Diane cuckolds her husband too Grey, with Philip.”
“And others,” Diane added, “many others.”
“And this community that you mentioned, it’s like a community of people who are into cuckolding?” I needed to know more.
“It’s a hotwives group, yes. There are around ten of us, depending on our circumstances. You know me and Kassandra, and obviously Melissa. Victoria used to be part of our group too before she settled down with her current boyfriend.”
Wow, all of this was hitting me like a ton of bricks, but Melissa didn’t seem nearly as surprised.
“Was I set up?” Things were dawning on me.
“No Grey!” Melissa said emphatically. “I discovered all of this stuff at the same time that you did. Well, maybe a little before. When we went to the sex shop and met Kassandra for the first time… I stayed behind a while longer while you went and got the car, remember?”
I did.
Kassandra found out that Diane had sent us, she assumed I was a new addition to their hotwives group and I was breaking you in as my new cuck so she kind of played dumb. It was only after you left to get the car that she spoke more openly with me, and that was the first I’d heard about any of this. When I explained to her that we were both new to this lifestyle she offered to mentor me.”
I felt a bit better knowing that Melissa hadn’t been lying to me this whole time, but something wasn’t adding up.
“What about Victoria? You’ve been friends with her for years, you didn’t know that she was into this? When you first tried to set me up with her, you weren’t setting me up to be her cuckold?”
“No! Not at all! I knew that she preferred black guys, but also knew that she occasionally dated white guys too. I guess I knew that she sometimes cheated on her boyfriends, but I never made the connection that she only cheated on the white ones with black guys. I didn’t know anything at all about this lifestyle.”
“So when the two of you caught me masturbating and we ended up coming here the first time…”
“I swear, I didn’t know anything! Victoria told me that Diane was a relationship expert who specialized in alternative relationships, that’s all I knew.”
Diane interjected for the first time in long time. “I think that you guys are having a really open and honest discussion, and that’s wonderful, but I feel the need to contextualize things a bit – to offer some clarity.”
Both Melissa and I were interested in what she had to say and encouraged her to go on.
“Grey, the first thing to know is that Melissa is telling the truth. Our little group is always looking for new additions and when Victoria learned a little bit more about your situation she thought that Melissa would be a good recruit for us and thought that it was something that you might go along with too. There was no plotting and planning though, that’s not how we do things. We have a bit of an eye for people who might be good fits and we expose the lifestyle to them, but it’s entirely up to them if they gravitate towards it or not. You guys did, and you did so naturally. The journey that you went on to bring you here was your journey.”
She spoke with a calming reassurance that made me believe her.
“When I gave you the advice to wear chastity, as unconventional as it was that was honest professional advice and not some attempt to lure you in. You can’t argue with the results can you? Look at you two, you’re a happy couple and you heard Melissa say it herself that if it wasn’t for chastity she never would have considered being with you. The fact that Melissa mentioned me to Kassandra, and Kassandra made an assumption that steered you to where you are now – that was all happenstance, or perhaps fate.”
Diana was looking at me expecting a reply, but Melissa jumped in.
“And Kassandra has given me a lot of great advice, which is kinda why we’re here. What she said made sense to me, but you’re the expert so I wanted to run her suggestions by you to see what you think.”
“Kassandra does indeed know her stuff, but I’m happy and flattered that you think so highly of my opinion. What did Kas have to say?”
“Well, her first suggestion was that I only date black guys…”
“…that’s a given.” Diana shot back without hesitation.
Melissa smiled before continuing, “the second was that I train Grey to service me orally and the third was that Grey not be allowed to cum unless he eats it up afterwards.”
Diana nodded with a smile, apparently impressed with the advice that Kassandra had given. “I think that’s outstanding advice, and I know exactly where she’s steering you. She knows the lifestyle well and how to get the most out of it. And so?”
“Dating black guys is great. Kas set me up with a friend of hers named Tayshaun and it was incredible!”
“Ah, Tayshaun” Diana said with a knowing grin.
“You know him?” Melissa was curious.
“Tayshaun is Phillip’s brother. They have a lot in common.” The two women smiled and laughed.
I really didn’t like how all of these things were related. I thought that this would be some side thing that I could keep hidden, but now I was learning that all of these things were connected and it really had me worried.
“And the other things?”
“You’re not going to believe this, but virgin-boy here has gone down on me twice and it was great both times. He’s a natural!”
“Congratulations Grey” Diana said with an approving nod, before her lips cracked to form a wicked smile in anticipation of her next question. “And you eat your cum now too?”
“He does!”
“Just once” I said, trying to reclaim some dignity.
“But you’re committed to do that from now on, right?”
“Yeah” there went my dignity.
“Well then, this is all excellent news! Kassandra has indeed put you on the right path.” Diana paused and turned to make eye contact with Melissa. “And would I be right in assuming that she made some other suggestions as well Melissa? Some things that perhaps you’d like to discuss privately?”
Melissa looked a little nervous, but agreed with Diana. “Yeah, I think that would be best.”
“We’re almost done here, Grey – why don’t you go wait in the car while Melissa and I go over a few last things?”
I really wanted to know what all of this was about, but I knew that neither were about to let me in on any of it just yet. I gathered my things and made my way to the front door. Before leaving Diana shouted out “Congrats on discovering your talent with your tongue and on getting your first hand-job, bravo!”
I went and sat in the car for what seemed like hours but was probably only 45 minutes or so. Eventually Melissa came out. The nervous look that she had on her face when I left was gone, replaced with a happy glow.
“What’s got you in a good mood all of a sudden?”
“Diana is amazing! I really wasn’t sure about some of Kassandra’s advice, but Diana agrees with her and spent more time explaining why each step was some important. I get it now, and I’m excited to give it a go.”
“Are you going to let me in on what’s going on?”
“In time, yes. Soon actually. For now I’ll just say this – you’re going to do some things that are going to make me happy, and then I’m going to do something for you that’s going to make you very, very happy. The first step starts this weekend. We’ve been invited to a party and I really can’t wait!”
I was willing to do anything to make Melissa happy, and that defined our relationship up until that point anyway so nothing seemed new there. I was really captured by her saying that she was going to do something to make me ‘very, very happy’ – that sounded great. I wondered how this party fit in to it all though. Fortunately, I thought, I only had a few days to find out.
Aeryn
- 22.09.2022
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- Cuckold
