Midlife Awakening Unleashed: A Forbidden Romance

What the fuck is wrong with me? I am forty-six years old. Why am I fantasizing about a twenty-three-year-old kid?
It was two a.m. and I was putting my sheets in the wash. I could not stop masturbating since I dropped Jen off at her house. I couldn’t get her body out of my mind. In fact, I hadn’t been able to get her out of my mind since we started going to the gym together. It was as if the more time I spent with her, the more attractive she became to me. At times, I caught myself trying to peek in her shower stall to catch glimpses of her. But today, I actually saw her naked. She wasn’t that little girl anymore. Those tan nipples, that long hair… I always thought she was beautiful, but working out made her body more toned. And our conversation at the café was… I don’t know, but I surely blew my cover. I had asked if she had her eyes on any boys, and she turned it around and asked if I had my eyes on any girls. I blushed like a shy schoolgirl! I didn’t even know black people could blush!
“Come on, tell me,” she said, laughing, showing that pretty white childlike smile.
“I can’t.”
“Well, you asked me about guys! I can’t ask you about girls? At least tell me about her.”
I threw my hands up. “Okay! Okay! She is a lovely sweet girl, a bit younger than me, really smart, really pretty, but I don’t think she would be interested in me.”
“Why do you think that? Isn’t she gay? It’s not like you’re ugly or anything.”
“No, she’s not gay. And I don’t want to approach her because I would hate to lose her as a friend.”
She put her hand on my arm and tried to sound as mature as possible when she said, “Well, wasn’t it you that told me there are times when you have to go with your heart and not your head?”
It’s true I did, but, this was a sticky situation. I quickly changed the subject and the topic was never brought up again. When I dropped her off at her house, I pecked her on the cheek as usual and watched her get into the house safely.
When I got home that night, I didn’t know what to do. Had I hinted too much that I was an old perv? Well, I wasn’t a perv because she was twenty-three. But still, I’d known her since birth! I decided to get online and do some work. I run an online clothing store that was so prosperous that I was able to afford a big five-bedroom house that I didn’t need. I lived there alone, no husband, no wife, and no children. I didn’t even buy the house with the intent of having any of the above; I bought it just because I could afford it. I was looking at some cute lingerie when I got an IM… from Jen! I opened it.
Jen: Hey, Sis
Charlotte: Hey, babe (The fact that I thought about her like that and she called me Sis made me sick to my stomach) “What’chu doin’ up this late… or early?
Jen: Nothing just sitting here thinking about what we talked about earlier. It’s sad you feel you can’t ask that girl out.
Charlotte: I didn’t say I can’t, I said I am scared to.
Jen: Well is she a good friend?
Charlotte: Yes
Jen: Does she know you’re gay?
Charlotte: Yes
Jen: So a good friend should take it as a compliment, shouldn’t they?
Charlotte: Ha ha I wish it was that easy!
Jen: But why is it hard? I would take it as a compliment.
Whoa! Was she…did she know it was her? Maybe I should fish for info.
Charlotte: Really? Even if you weren’t gay or bi?
Jen: Well maybe some people keep it a secret better LOL
Charlotte: Maybe they do LOL. Listen babe, I got to go. Getting tired. I’ll hit u up tomorrow. Hugs - xxxxx
Jen: G’nite and you’re welcome - xxx
When I hit that little red x in the top right corner, I couldn’t believe how much I couldn’t wait for Monday so I could see her at the gym again. I returned to my lingerie shopping when I got an idea.
Charlotte: What you doing tomorrow?
Jen: Nothing, watching the Adventure Time marathon. Y, whaddup?
Charlotte: Well, I got some gift cards and wanted to know if you wanted to go shopping with me
Jen: You need fashion advice too? :)
Charlotte: Yeah. You know I’m helpless without you! LOL
Jen: Hmmm… food? Yes, no, maybe?
Charlotte: Yes, Fatty McFat! LOL, jk. It’s a deal
Jen: A deal or a date? LOL
Oh shit! What do I say?
Charlotte: Both for you, gorgeous LOL
Swag…are we flirting?
Jen: Well, you know me, anything 4 food. Do I get to try stuff on 2?
Charlotte: If ur good, I might even buy you something. :)
Jen: Yay! See u tomorrow - xxxxxxxx
Charlotte: Byyyye! xxxxx
This should be fun!
The next morning I put on my white lace panties, no bra, and a brown low-cut sundress. The sundress had a split on both sides that crept up my thighs almost to my waist. The dress was halter style and tied behind my neck, showing off my arms and my back. I put on my gold watch, three gold bracelets, and my gold sandals. I sprayed my ‘fro, ran my hands through it, got my keys, and left.
When I pulled up, Jen was sitting outside. As she walked to the car, I saw she was wearing a navy blue cotton skirt with white horizontal stripes and the hemline stopped right beneath her butt. She had on a V-neck white tee and a cut-off denim jacket and she clearly wasn’t wearing a bra either (the jacket must be so Kathryn wouldn’t see her without a bra on).
“Wow, you look great, Jen!”
She blushed a little. “You look pretty hot yourself, Sis.”
There went that name again. She got into the passenger seat and leaned over to kiss me on the cheek as usual, but at the last second, I turned my head and her kiss landed on my lips. It was only a quick second kiss, but her lips felt soft against mine, and as I pulled back, she looked shyly out of the window. Oh no. We said nothing and we set off for the mall.
It was Saturday, and Lynnhaven Mall was busy with women doing shopping stress relief while toting around their demon spawn. It seemed as if every kid was drooling either from their mouths or their noses. When we passed a toy store, there was nothing but little children screaming for things they wanted that their parents had no intentions on buying. I was disgusted. Why, as a parent, would you even set yourself up for the embarrassment? If you didn’t have a plan to buy a toy, why go in the store? And why don’t parents beat their kids anymore? Had I screamed because my mother wouldn’t buy me something, she surely would have smacked me twice and set me straight. Hmm. I didn’t have kids for a reason.
We window-shopped a little and then I dragged her into Lu Lu’s Boutique. Lu Lu’s is a really nice locally-owned lingerie boutique, one of my favorite stores. The lady who owns it has candles burning, and every time I inhale, I take a deep breath of something wonderful. That day, it was pumpkin spice. The walls were painted orange and pink and there was a glass table with a five foot tall orchid centerpiece placed carefully in the middle. Sprinkled on the table were decorative crystals, and wrapped around the table was a circular orange ottoman in the center of the whole store with pink pillows on it. Lu Lu also baked miniature cookies that she kept in the back of the store between the edible underwear, alcoholic whipped cream, and edible body butter.
I picked out six pieces of different types of lingerie and dragged Jen into the fitting room with me. As soon as I had drawn the curtain, I pulled the sundress up over my head, revealing my lace panties. I saw Jen trying not to stare, but it was hard for her…good. I tried on piece after piece of lingerie, bending over melodramatically when I had to take off something or put something on.
“Are you going to wear one of those for your lady friend?”
I giggled. Of course, baby! I wanted to say, but I didn’t answer. “Which one do you think I should get?”
“Well, the one with the breasts cut out is tacky. The green one, that’s nothing but lace, so that’s awesome. And the leopard trimmed in red really looks good against your skin.”
“Well, I’ll get those two, since you like them so much.”
“Well, my opinion is not important, the mystery girl’s is.”
“Do you have lingerie?”
“No,” she laughed. “Boys get turned on whether you’re covered up like a nun or not. Lingerie isn’t needed.”
“Wait here.”
“What?”
I went out into the store and came back with four pieces of lingerie. “Try these on.” I thrust the items at her.
“What?”
“Jen Marie Matos, if you say ‘what’ one more time, I will put a hurtin’ on you.” I gave her a look that showed I meant it.
She stood up, stripped down to her pink thong, and looked at me as if she had never done that before. I helped her into the different pieces of underwear. We laughed as she made funny poses. I took my phone out and took some pictures, and she laughed. Then she put on a black one. It was all black except for a tiny red bow between her breasts and below her navel. The top was like a tank top, but with the midriff cut open to show her smooth stomach. It stopped at her waist to show her black lace thong.
“You look amazing in that one.”
She turned and looked in the mirror, and at the sight of that perfect ass, I crept up behind her, put my arms around her, and pulled her in closer to me. We looked at each other in the mirror.
She turned to face me. “Am I the girl?”
I kissed her, slightly longer than when we were in the car, but still merely a peck. And then, looking deep into her beautiful gray eyes, I said, “Of course it’s you!” Then we kissed properly.
As I felt her young, tender lips against mine, something came over me. I felt young and wild. She let my tongue inside her mouth to enjoy the party. I caressed her back, keeping her body close against mine, and then moved my hands down to her bottom. I indulged in her kiss; I quickly forgot where we were. All I wanted was her, to touch her, to kiss her, and I didn’t want to stop when I did.
“Let’s go to my place.”
She didn’t say anything, just kept breathing heavily. “You need some help getting dressed?”
She nodded. I undid the clasps that were holding the teddy together, and at the sight of her free breasts, I was turned on even more. She moaned loudly as I sucked on her nipples. I pulled her thong down with my teeth, and she whispered frantically, “No, no, no!” I licked her pussy lips with one sweep of my tongue and then hurriedly got her dressed. When we stepped out of the dressing room, the clerk looked at us. She had heard.
“Problem?” I asked.
She gave me a disgusted look. I took a handful of cookies and threw a look back at her. “Let’s go, Jen.”
In the car, I could tell she was still in a daze, but I pulled her face in my hands and kissed her deeply. As I pulled away, I said, “I have wanted this for so long! You have no idea.” I started the car and drove as fast as I could to my house.
As we walked into the house, Jen turned around, looked me in my eyes, and said, “I’ve never done anything like this with a girl before, but I’m so happy it was me you wanted.”
I smiled. “I want you more than you can ever imagine. Come on.”
I stuck out my hand and led her to my bedroom. The room was a decent size with a king-sized bed in the middle and two nightstands on either side of it. Atop the night stands were two table lamps and inside the night stands were my “little helpers”, things I had that helped me from time to time with my orgasms. There was a vanity dresser on the far wall and a bathroom to the right of the bedroom door. I undressed her and then myself.
“Do, you trust me?” I could see the nervousness on her face.
“Um, sure.”
“Good.” I took a towel from the bathroom and laid it on the king-sized bed, “Lie down and close your eyes.” She gave me a confused and scared look. “Trust me.”
She lay down. I went down the hall and came back a few moments later. When she heard my footsteps come in the room, she lifted her head.
“I can see you like to peek. I’m going to have to fix that,” I pulled out a blindfold from my nightstand and gently pulled it over her eyes. I stroked her soft pubic hair and turned on my surprise. She must have thought it was a vibrator because she opened her legs a little wider as if inviting pleasure to come. I couldn’t help but laugh as I moved the object from the top of her pussy to the lips.
She gasped. “Oh my God! Are you shaving me?”
We both burst out into laughter and I couldn’t go on, I was so weak. When I finally regained my composure, I turned the clippers back on and continued shaving. I had fantasized almost every day of tasting Jen with my tongue and smearing her juices all over my mouth, but in none of my fantasies did I enjoy a mouth full of hair! I separated her legs a little more, squirted shave gel on her, and gently caressed it into her skin. As I took the razor to her skin, I kept my thumb on her hard clit, playing with it and teasing it. The whole time I was shaving, Jen was moaning little, sweet moans, and when I was satisfied with my masterpiece, I turned the clippers back on and rested them against her clit as I buried two fingers deep inside her hole. Her body lifted up automatically as she yelped with an incredible mix of tingles and sparks, and it was only seconds before she hit the orgasm I had worked so hard in building for her. She giggled; I smiled. I kissed on her chest and neck, slowly working my way up to her lips. She threw her arms around my neck and kissed me greedily. As we kissed, I put her hand on her own pussy.
“Feel for yourself.”
She felt her smooth pussy and started to play with herself while I caressed her breasts and pinched her nipples. She started to move her hand.
“Keep going, you’re turning me on.”
She did. I put her free hand on her breasts and she got the message. She played with her breasts with one hand and the one touching her sweet pussy moved faster and faster. I couldn’t resist touching myself while I tried to imagine what she was thinking behind that blindfold.
I had an idea. I left her fighting her fingers for an orgasm. When I came back, I moved her hand and climbed on top of her. As I entered her dripping wet vagina, she yanked the blindfold off and her face was full of fear. She hadn’t expected me to be on the other end of that penis. The dildo hooked up to my harness was so lifelike, not like the hard rubber ones that are sold in the stores, but more natural and a whopping eight inches. I started fucking her like a man and her shock disappeared. She pulled me to her, pinching my nipples as she kissed me, and my thrusting got faster. After a few minutes of violent thrusts, nipple sucking, and tongue kissing, we reached our orgasm together, and I only wish I could fill her pussy full of man come.
To my surprise, when I pulled the big dick from inside her, she sat on her knees and licked her juices off the dildo. Then she shoved all eight inches down her throat until her nose touched my stomach. Impressive.
“I used to practice on my toys when I was with Tony, and,” she giggled, “I found out I don’t have a gag reflex, so sucking dick is quite easy.”
“Wow.” I lay down in the bed. “So, what do you think of your new smooth look?”
She looked in the mirror, did a Superman pose and smiled. I asked her again as she walked back over to the bed.
She kissed me and said, “I love it, but what’s more important is that you take care of it like you did today.”
I hugged her and said, “As long as you let me baby. I’ve wanted you for so long; I’m never going to let you go.”
“Well, I’m not going anywhere.” She hugged me for a bit, then she unbuckled the strap on my harness and threw it on the floor.
What is this kid about to do?
She straddled my body and began her kisses from the tip of my nose, across my lips, down my neck, down my tits, and she slowly moved down my belly.
“Oh my God, you are about to make every dream I’ve ever had come true.”
She just smiled and moved to my moist slit. Her kisses moved down my smooth skin, beside my small pussy lips. Between each kiss she gave a little twirl of her tongue on my flesh, and each time, her tongue moved closer to the most sensitive part of my body. My gasps and trembling increased until I yelled, “Please, just lick me, Jen! I’m begging you!”
She flicked her tongue from left to right across my swollen lips, each contact causing a jump from my body, and then she plunged her tongue deep into my hole. The top of her mouth covered the top of my lips and clitoris. I groaned with pleasure as she licked hard then soft and then added two fingers to my hole to add to the pleasure. I grabbed handfuls of her long hair, holding her head in place on my rock-hard clit. She nibbled on it and I screamed, begging her to do it again. She did…many times! I nearly knocked the poor girl off of the bed as I bucked like a pissed off donkey and my orgasm rippled through my entire body. She pushed her face deeper into me, her tongue as deep as she could reach, lapping up the large amounts of come my tightening pussy was forcing out. She kept licking me until I begged her to stop because I couldn’t take it anymore. I lay there panting and she crawled up the bed and kissed me. I smiled with my eyes closed.
“So, was that good for my first time?”
I opened my eyes. “It wasn’t your first time!”
She smiled and nodded.
I laid my head back and closed my eyes. “Fucking… awesome.”
She gently ran her fingers through my afro and then slowly traced her fingers over the skin of my shoulders and then down to my bullet-like nipples. I felt her get off the bed, and when I opened my eyes, she had my strap-on on and was looking at herself, stroking the lifelike penis in the mirror. She jumped as I came behind her and kissed her neck. My hand came around and started to caress her breasts and my other hand had a bottle of lotion which I squirted on her new penis. She stroked it more smoothly as if she was born with it and I moved away from her. She turned to see me bent over my dresser, my eyes fixed on hers in the mirror and a cute little smile on my face.
She walked slowly over to me and ran her hand over my tiny, sexy ass, all the time stroking that penis. She teased both of my holes with it, finally resting it against my pussy. I closed my eyes as my pussy lips stretched to take the width of her tool as she slid it fully into me with one slow movement. I moaned as it reached full depth and she pumped in and out. I knew this felt as good for her as it did for me because her moans were matching mine as the dresser shook with each lunge forward. I had my hand rubbing furiously on my own clit and I knew that the part of the strap that was stimulating hers was doing its job. We truly came together. She slumped over me and we both panted like thirsty dogs with our orgasms shaking our bodies. She slowly removed her thickness from me and come dripped from my vagina and down the dresser. I helped her remove her maleness. We climbed under the sheets and drifted off into a very contented, very relaxed sleep.