Jenola and Anita Ch. 01

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Waiting for Jenola to be paroled, I find a BBW fill in lover.
4.1k words
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Part 1 of the 3 part series

Updated 09/22/2022
Created 05/05/2013
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CONTINUED FROM "JENOLA THE BLACK BI BBW"

The next Thursday, six days later, I returned home and saw Jenola's next letter. I raced inside with it, but first sat down at my computer and lit a joint, so I could read her letter while fucked up. Her letter read:

Big wow to you, too, Steven! What you said about all the feelings being mutual is so right. It's amazing, I've only gotten two letters from you and I can already see how different you are from my two exes. That gives us a much better chance to last together. We are definitely on the same page!

Yes, I played basketball for my school team. When I was on the 8th grade team, I led the team in points and rebounds, but unfortunately I started smoking the next Summer. That hurt my play and I ended up getting benched on the 9th grade team, and then I got kicked off the team when I was arrested for shoplifting. After that, I stopped working out and got fat. So instead of getting a basketball scholarship, I moved in with my boyfriend after we graduated and I got pregnant with Britney. It wasn't the path I wanted to take but having Britney was better than playing in the WNBA and I'm glad I turned into something you like - a black BBW!

You'll do what for me?! Take me to as many WNBA games as I want?! Well then I'll just have to move out there so you can take me to all of them! And of course I've had lots of crushes on the girls in the league, and it'll be fun talking to you about which ones are the hottest! And you'll have to tell me about all the hotties who've come into the league since I've been locked up!

It'll be so much fun teaching you all my hobbies. I don't think I look hot when I do them, but if you think so, hey, that's great with me! I do feel sexy when I dance at raves and I hope you like watching it!

My chin almost dropped to the floor when you said that I'm "one fucking hot slab of chocolate" like Missy Elliott! Oh shit, that's the most amazing compliment anyone ever gave me, since I idolize Missy so much! I hope I live up to your expectations! I'll do my best!

I sure hope you're right that my daughter will forgive me and understand. I've still never talked to her about my crime. My mom has a little bit, but I told her to let me do most of the explaining when I get out.

Wow, I'm so relieved that you know what I did and accept it. I was so afraid that you wouldn't want to be with me anymore if you knew. And that gives me a lot more confidence that our relationship can work.

And yes, it's so good that I know why I committed the crime. My two accomplices and I were all desperate for money and they came up with the idea. I knew it was wrong and I didn't want to hurt anyone, but I didn't have the will power to say no to them, and I didn't think I'd get caught and be apart from Britney.

My counselor helped me with my self esteem and also realize who my real friends were, so I don't feel the need to give in to peer pressure anymore. I know that you, Britney, Kim, and my mom are the only people who matter. And I will treasure my time with all four of you even more because of the years I couldn't be with you in person!

I look forward to going to hookah lounges with you! And it's funny that you think the smoke is so sexy, because that's why I started smoking! I thought cigarettes were sexy, and then I saw how much smoke comes out of a hookah pipe! And it will be hot to watch you do it, too!

You're right that being out is best because you know who your friends are, just like when people know why you got locked up.

I don't know why, but I've always like white guys and black girls best and I think that's who my relationships will always be with. And I'm glad that you would accept me either way but like that I'm bi!

Did anybody ever tell you that you should be a counselor, too?! What you said about being lucky to have three people who never turn their back on me, and about quality over quantity, is exactly what my counselor said to me! I wish I'd learned that so long ago, but better late than never, and that's why I'll have a much brighter future! And yes, I'd rather you be the only guy who answered my ad than 1,000 other guys!

I know you'll be as great a conversationalist in person and I promise I will be, too! And oh shit, you should've seen me when I read your line about us saving saliva for the kissing! I LOVE kissing! When the other person is good at it, sometimes I like it as much as sex! I can do it all night and never get tired of it, and I think you're going to be the best kisser I've ever had!

You're welcome about telling you that you'll have kids someday, and I hope you're right about me having more! And if you ever want me to be the mother of your kids, just tell me and I'll be happy to give that to you!

I'm glad you have such a special sister and stay in touch with her so much. And I hope you two will live closer again someday.

Oh yes, I hope we quote Missy Elliott lyrics to each other all the time - especially the explicit versions! I already have several in mind and I bet you do, too!

I also wish I knew what the future held for us! Where's a crystal ball when I need one?! But like you said, it'll be worth the wait!

Yes, we need some time to figure out if we belong together as a couple, but we have to find out and even if we end up being just friends, that'll still mean a lot to me, because you're already one of the best friends I've ever had, and I could never stop being your friend, ever.

You're very welcome for coming into your life, and thank you for the same!

Love,

Jenola

That letter convinced me that Jenola and I would almost certainly be more than friends and have a good chance to be boyfriend and girlfriend for the long term.

But, having been masturbating like crazy many times over the last several days while thinking about her, I also realized that I had needs to be taken care of in the meantime. So as soon as I finished writing that letter, I immediately went on Craigslist and started looking for a woman to fill that void. I didn't want to be promiscuous, as that's simply too dangerous, but rather I was hoping to find a woman, preferably in a similar situation, for an ongoing sexual relationship, and hopefully a friendship as well.

I browsed several pages of ads and found little or no interest in most of them. But one grabbed my attention, even though it wasn't what I was looking for. The headline read:

"Sexy BBW looking to entertain for $"

I clicked on the ad and it read:

"I'm a sexy white BBW with 44DDs looking to make some money to help with the bills. No sex or touching, but I will put on a great show for you."

I immediately wrote to her:

"Hi, I have a huge attraction, no pun intended, to BBWs. I'm sure your 44DDs are luscious, but my favorite part of the female body, by far, is the sole - the bottom of the foot. I know you said no sex or touching, but would you let me lick the bottom of your feet?"

I saw a response from her the next day, Friday, when I was about to leave for work:

"Yes you can lick the bottom of my feet. But they're kind of rough because of no money for pedicures. Not sure if that makes a difference. And how much would you pay me?"

I immediately responded:

"Great, I'm glad you're into that and I hope you enjoy it! At least I'll love giving it to you! And it's okay if the bottom of your feet are rough, as long as they're clean! How does $40 for an hour sound? And if I'm happy with our first session, I'll consider paying for you to get a pedicure and having you over once or twice a week. Let me know!"

When I got home from work, I had a new message from her:

"$40 for an hour is fine. And I really need the money, so the more you want to hire me the better. When do you want to do this?"

I immediately responded:

"Hopefully tonight, or at least your earliest available opening. Call me and we'll work out the details."

I put my phone number at the end of the message and in about two minutes, I got a call that the caller ID listed as "number blocked." Figuring that it was probably her, I immediately and enthusiastically answered.

She sounded middle aged and spoke in a soft monotone with no emotion, and had a rough voice, as if she were a long time smoker. The conversation lasted just about two minutes and we made arrangements to meet that night at midnight. I tried to get a friendly conversation going, but she seemed uninterested in it and to simply view this as a business transaction. Once she knew my address and the meeting time, she simply said "Okay, see you then," and hung up without even saying goodbye.

That night at 9:45, I ate a weed brownie. I smoke weed more than I eat it, because I like to get fucked up right away. But I chose eating in this case so that my mouth wouldn't be too dried out to worship her soles as zealously as I wanted to. Furthermore, when I eat weed, it usually takes me about two full hours to get totally fucked up, which is why I ate when I did. Because weed makes me so horny and causes me to focus more intensely on the things I'm passionate about, I definitely wanted to be totally fucked up for this session. And furthermore, I get more fucked up through eating than smoking.

At 11:58, the phone rang, again reading "number blocked." I immediately answered and she told me that she was inside my apartment complex but having a hard time finding my apartment. I asked her to describe where she was. She did and I guided her from there. Knowing that she was close, I opened the front door and peeked out, nude and with a massive hard on sticking straight out.

I saw headlights round the corner and asked if that was her. She says yes, so I opened the door widely and told her I was right in front of her. Saying nothing but "Okay," she hung up the phone and parked right in front of my apartment, next to my car.

She opened the car door, got out, and slowly walked up to me. Because my apartment complex was rather poorly lit, I could barely make out any details of her appearance.

Finally, when she stepped onto the welcome mat, I could tell that I very much liked what I saw. She looked about 40-45 years old and was 5'5" and 250 lbs. with thick, curly, and frizzy blonde hair that went almost down to her waist, and the top of her feet were awesome, getting me even more excited about seeing the bottom. She was wearing a plain white sleeveless shirt, a gray elastic pair of gym shorts, and a pair of white flip flops. She was wearing no make up of any kind. In short, she was dressed as if she had little money and was doing this out of desperation. She also had a very large tattoo that covered much of her upper right arm.

"I'm Steven!" I said smiling.

"I'm Anita," she responded, in the same tone as on the phone.

I stepped out of the way and, as soon as she walked in, locked and chained the door, then stood face to face with her. Acting very business like, she took off her shirt, revealing that she wasn't wearing a bra, then dropped it on the floor. That was followed by lifting her right foot a few inches off the ground, slightly bending it downward, and spreading her toes apart, causing the flip flop to slip off. It was a huge turn on for me to watch and she then did the same thing with her left foot, then slipped off her shorts, revealing that she wasn't wearing any underpants, and dropped them on the floor. And the more she stripped, the more tattoos I noticed.

Now completely nude except for a watch and nipple rings, I saw that her body was very well proportioned with knockers, thighs, and ass cheeks that shook up and down line gelatin - even when she was standing still.

As soon as her shorts hit the floor, she asked, as if she wanted to get this done as soon as possible, "So where are we going to do this?"

"Hold on, I want to see your tattoos," I said. I circled her body and noticed eight tattoos - not an extremely large number, but all of them were pretty big and looked very professionally done. Most seemed to have comic book influence. After about a minute, I decided that it was time to see, and worship, the two things that I was craving - her soles. "Sit down and spread your legs out across the couch," I told her.

She did, sitting on the right side of the couch. I then joined her on the couch, sat cross legged and facing her, grabbed her by the ankles, and rested her soles on my thighs.

"Oh shit!" I gasped in excitement. "Your soles are fucking amazing!" They looked like a wide pair of size 8 1/2s with a ring of fat around each toe, and the bottom of each toe having a very puffy appearance. Her arches were fairly low. The skin was somewhat dry and flaky, but she seemed to do a great job keeping them clean.

I was about to start the worshipping when suddenly I noticed that she was sniffing a lot. "Do you do weed?" she asked.

"Oh, fuck yes!" I exclaimed. "In fact, I'm stoned out of my fucking mind right now!"

"Really?!" she responded, smiling and showing enthusiasm toward me for the first time.

"Yes! Do you do weed, too?!"

"I did. I was an every day user until my husband left me a few months ago, and I haven't had any since."

"Do you miss it?!"

"Oh, fuck yeah! I've been going ceazy to find someone who can get me some!"

"Well then you came to the right place!"

"Hey, listen, I really want some bad, so if you want, you can just pay me in weed for our sessions; no money."

"Wow, that's a great offer, but I'll be glad to pay you in both."

"You'd really do that?" she asked, sounding shocked.

"Yes. You said your husband left you, and I figure that's why you need money so much, and I bet you have some kids to feed."

"Yeah, three."

"Exactly. So I'm going to take care of both of your needs, money and weed, while you're going to take care of my need, which is female soles!

"It's a deal!" she said, now grinning.

"Great! Would you like some weed now?"

"I'd love some, but I better take it to go, since I have to drive."

"I understand, but maybe some night I can pay you to stay with me the whole night and we can get fucked up together while I worship your soles."

"That would be fantastic!"

"Oh yeah, definitely! Would you be able to get a sitter for your kids?"

"They're 17, 13, and 10. I can leave them by themselves for a night once in a while."

"Oh, cool!" At that, I started massaging her soles, digging my fingers deep into them. She lay back and gasped, sounding like she was in not only in ecstasy, but also amazed. "You like that, Anita?" I asked.

"Oh yeah! I had no idea this would feel so good!" she enthusiastically responded.

"This has never been done to you before?!"

"No! When I knew you were going to work my feet, I thought it would just be really fucking weird, but I actually love it! I see what I've been missing out on for all these years!"

Hearing that, I decided to take it to the next step. I cupped my right hand around her right heel and my left hand around the top of that foot, then lifted it up and thoroughly worshipped it.

I spent over an hour kissing, licking, and sucking her luscious soles as she lay back and enjoyed discovering just how much she loved being the recipient of my sole fetishism.

After I'd been worshipping her for about 15 minutes, she began using her left hand to play with her nipples and her right hand to play with her clit. A few times, she even licked her nipples. She came many times from the clitoral stimulation. She didn't speak or moan the whole time, but when she came, she frequently gasped and breathed heavy, looking like she was very turned on, while her body greatly tightened. And for much of the worship, she had her head thrown back on a pillow.

Finally, she looked at her watch and saw that it was 1:25. While I was worshipping her left foot, she grabbed my still massive hard on, which was now soaking wet from pre-come, between her biggest two toes on her right foot and began twisting the head. Staring at and worshipping her two phenomenal soles while fucked up kept me extremely turned on, and one of those soles now actually touching my cock - that drove me over the edge.

Within a few seconds, my whole body was filled with an amazing orgasm and I shot a massive load. As soon as Anita saw the come, she jerked her left sole away from my mouth and placed it in front of my cock. I covered both soles entirely with my come, then licked it up and swallowed it.

As soon as I finished, I looked up and Anita and she was grinning. "Well, this was definitely the most interesting session I've ever had!" she said.

"Is that good or bad?! "I asked.

"Good! I had a great time, and you definitely changed my mind about foot guys! I had no idea how much I'd love it!"

"I'm proud to have been the one who got you into it!

"Me too!" Then, while getting up and walking over to her clothes, she said "Unfortunately, I have another appointment at 2:00, so I have to get going, but please let me know as soon as you're ready for our next appointment!"

"I will! You need the money and the weed, and I need the soles!"

"Yes, but I really did have a great time with you!"

"As did I with you, and I look forward to many more!"

"Oh, me too!"

At that she started getting dressed while I got her payment ready, all from a cigar box on the coffee table. She first put on her shirt, then her shorts, then her flip flops. As soon as she was fully dressed, I handed her three $20 bills and a brown paper bag containing a large sandwich bag containing five joints and two weed brownies.

Upon seeing the money, she tried to give me back one of the $20 bills, saying "We agreed on $40, not $60."

"Yeah, but we also agreed on an hour and you've been here a little over an hour and a half!"

"Hey, I stayed because I wanted to, and besides, since you're going to be my supplier, that's the least I can do!"

"I appreciate that, but please keep it; you need the money more than I do. You can use it on your kids."

Anita thought about it for a few seconds and reluctantly decided to keep the money. Then she pulled out the sandwich bag and looked at it's contents. "Will that get you until you come back again?" I asked.

"That depends on when you bring me back!"

"Well, I was thinking we could get together one evening during the week and once on the weekend."

"That would be great!"

"So will that be enough weed to get you by until Tuesday."

Anita thought about it for a few seconds and responded "Probably. Unless my oldest daughter finds it!"

Upon hearing that, I quickly grabbed a couple of more joints out of the cigar box and, while putting them in the sandwich bag, said "Then here are a couple for her!"

"Thanks! She's been missing it like crazy, too" Anita said smiling. Then pointing to the brownies, she asked "Do those have weed in them"

"Yes!"

"I've never eaten it before."

"You're going to love it! It's the best!"

"Mmmmmmmmmm, I'm excited just thinking about it!"

"I'm excited just thinking about you doing it!"

"Is there any trick to it, or so just eat them and get stoned?"

"You just eat them and get stoned! Now it takes a couple of hours to get totally fucked up. But when you finally get there, wow, it's the ultimate high!"

"Wow!" Then looking down at her watch she said glumly "I really have to go, but I don't want to."

"I know. I'll have to book you for a longer session next weekend!"

"That'll be great!"

"Oh yeah! And I can hardly wait to get fucked up with you!"

"Same here!" Right after saying that, we gazed deeply into each other's eyes for about 30 seconds and I felt it was very intimate, as if we were starting to fall in love. But even though she bent her no touching rule for me, I stood a few feet away from her, not wanting her to feel uncomfortable.

But then she opened her arms widely and said "Come here, Honey." At that, my nude body walked excitedly up toward her and we had a tight embrace. After a few seconds I kept our bodies tightly together but moved my face back so that our eyes were just a few inches apart.

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