by Jessica Sin
A small moan came from her room. ‘It’s probably nothing,’ I first thought to myself. She probably just woke up from her nap and was stretching in her bed. Then I heard it again, but this time it was louder and more distinctive. I’ve been with enough women (and have seen enough porn) to know whether that kind of a moan is sexual or not- and clearly it was.
My mind quickly went from school work to being in a state of frenzy. She was obviously masturbating in her bedroom with her door wide open. She had no clue that I had already arrived home because she was sleeping, and if I wanted to, I could quietly have a look at what she was doing to herself. But could I? Could I actually spy on her doing something so personal and so private?
I knew I shouldn’t have, but I couldn’t resist. Curiosity had gotten the better of me and so I quietly stepped into the hallway and took a peak inside her bedroom to see Elisha in the most vulnerable position I had ever seen her in. She was completely bare from the waist down. Her pants, pantyhose, and undergarments were all off. Her professional business suit on her upper body was still worn nicely, with her jacket and blouse still properly buttoned up. Her hair and make up were still neat, showing that she just arrived home not too long ago.
But it wasn’t just the lack of clothes which grabbed my undivided attention, but what she was doing to herself. There was a faint buzzing sound in the room. Her milky white legs were spread wide open and she was using a vibrator on herself- pushing and pulling it, in and out of her vagina.
I was mesmerized by the sight of my prim & proper friend masturbating herself with such intensity. I couldn’t believe how aroused I was becoming just by watching her. I loved the sight of her clenching her eyes shut, which brought out the slight wrinkle lines on her face. Her chest was moving up and down from her ever-increasing heart rate. She was soaking wet down there with her vaginal fluids brightly glistening along her brown labia and thick pubic hairs.Her legs were slowly moving and her feet were curled up and clenched tight. And of course her fingers; her fingers were still busy at work, taking turns rubbing her clit and fingering her dripping wet vagina.
In all our years of living together, she has always been the symbol of morality and purity. Of course she enjoys sex like anyone else, but actually seeing it person with her face twisting & turning was an utter shock to put it lightly. But what was equally as shocking was noticing that I was becoming HARD watching my her masturbate like this. But suddenly, as her leg muscles clenched and showed signs of an impending orgasm, her eyes opened in a flash. And that’s when she caught me, lifting her head up to see me watching her.
I immediately turned away and headed back to my room, hoping deep down that Elisha would stupidly think that I was just walking by and caught just a split second of what she was doing, rather than just standing there and spying on her.
She came out of her room to follow me. Her pants were sloppily thrown on and she was barefoot. And her shirt was untucked. She obviously wanted to explain herself, as we both faced each other with the same mortified look on our faces.
She was struggling for words before finally saying, “I’m so sorry you had to see that…I had no idea you were home….God, I’ve never been so humiliated in my entire life.”
She was almost in tears as those words came out of her mouth.
“It’s okay,” I replied, trying to comfort her. “We’re all human and we all have our needs. Don’t forget how many times you’ve caught me doing that growing up. It’s not that big of a deal.”
“But you weren’t supposed to see me like that. I can’t imagine how lewd and vile that must have looked to you. We’re friend and this just isn’t right. And why were you even WATCHING me in the first place?”
“I don’t know…I guess it just kind of happened,” I stammered.
Her response to my answer was to simply put her head down in shame. She looked crushed that I not only saw her in the state that she was in, but was actually spying on her.
I reached out and patted her on the shoulder. “Come on, it’s Valentine’s Day, and neither of us have a date tonight. So instead of sitting around feeling depressed over this, I’ll take you out to a nice restaurant for dinner. It’ll be fun.”
“You don’t have to do that for me. But thank you for the kind offer though,” she said appreciatively.
“Nope, you’re going. And I won’t take ‘no’ for an answer.”
It was late in the evening when we arrived at the restaurant. It felt like a date the way she had dressed up for the occasion. And to my surprise, she wore a sexy tight fitting black dress with a plunging neckline, showing the center of her bare chest, just above her bra. Her hair was elegantly done as was her neatly applied make-up. Simply put, she looked stunning.
***
“I never thought my Valentine’s Day dinner would be with my housemate of all people,” Elisha said jokingly as we ate.
“Believe me, I didn’t expect this either. But it’s a heck of a lot better than watching you sit on the couch all night watching dvd’s of romantic comedies that you’ve seen a million times- no offense, but it’s a sad sight. Especially on your favorite day of the year.”
“I guess you’re right. Thank you for taking me to such a nice restaurant. I should be a little more appreciative towards you for this,” she said with a playful wink.
“No problem. But that raises the question; what’s a woman like you doing being single on Valentine’s Day? You’re a real catch and I’m sure you can have any man you want.”
“Well, you can take your pick of reasons. For the last few years it’s been my hectic studies which has led me to have to cancel dates, making the guy think that I’m either cheating or that I’m not interested. And sometimes I can be a little too picky and my standards are a little high. I’m not getting any younger here and it would be nice to settle down with ‘Mr. Right’ before it’s too late.”
“I’m sure you’ll find the right guy soon enough. Like I said, there are lots of guys who would date you in a heartbeat,” I told her.
“That’s very kind of you to say. Anyway, enough about me rambling on about myself, let’s talk about you for a moment. You’re a handsome young man; how come you aren’t dating anyone?” she asked.
“Same reasons as you I guess. I’ve been really busy with school this semester, and frankly, a lot of the girls in college aren’t my type. I’ve always been attracted to older women to be honest.”
I quickly realized what my words meant in this conversation since she was older than me, and by the look on her face, she noticed it to.
“Older women huh?” she noted with an eyebrow raised. “Have you ever been with one?”
“No comment,” I playfully replied.
“And to think, I expected this dinner to be like any other night,” she smiled. “So tell me, what is it you like about older women? And was your first time what you expected it to be?”
“Do we really have to do this?”
She nodded and took a sip of her drink.
“Fine,” I replied. “I love the class and elegance of older women, and their confidence. And I love the way they look. The lines, the wrinkles, the soft skin; I think it’s all really sexy.”
“Hmmm…Now there’s an interesting answer. And how many have you been with? Were they pretty? Age?”
“I’ve only been with one, and it was amazing. She was in her mid-30’s and it was everything I expected it to be. And yes, she was really pretty. She actually reminds me a lot of you, with the same style and personality. Her body is shaped like yours as well.”
“Is that why you’ve been glancing at my cleavage all evening?” she asked with a little smirk.
“Very funny,” I replied. “It’s not my fault you wore such a revealing dress.”
“Well, you asked me out to dinner on Valentine’s Day, so I wore my Valentine’s Day outfit.”
“Fair enough. Now let’s turn this conversation back towards you where it belongs,” I said. “What kind of men are you i
nterested in?”
She took another sip of her drink and replied, “All kinds. I really don’t have a preference, just as long as he’s intelligent, charming, and is a real gentleman. The last two men I’ve been with were much older than me, so I wouldn’t mind being with someone younger for a change. But for now, it’s just me and my vibrating toy.”
For the first time this evening, I found myself at a loss for words because of her frank comment about what I saw her do this afternoon- a topic which I was sure wasn’t going to brought up again.
“You seem a little shocked hearing me say that,” she said with another smirk. “At this point, you shouldn’t be, you’ve already seen the goods.”
“I guess. But actually hearing you talk like that is just…different. I’m so used to being around the ‘perfect’ woman that I’ve become accustomed to. It’s hard to explain.”
She smiled. “I think I know what you mean. You know, it’s tough being single for all the years. And I guess, as a result, I’ve overcompensated a little and tried to hard to be ‘perfect’ as you put it. So, you naturally must have been stunned to find out that your conservative friend has a healthy sexual appetite which I’m SURE can rival some of the girls at your school.”
“So your sex drive is on par with the younger college girls? It kind of makes wonder what else I don’t know about you…”
Her eyes sharpened and she took an even bigger sip of her drink. “Well, if you’rethat curious about my sex life, if I’m not seeing anyone, I like to use my vibrator every so often in the bathtub so you can’t hear it. I either do it after work or before bed at night. And if I’m in an especially naughty mood, I’ll let it vibrate deep inside my anus while I rub myself. Nothing relieves stress better than that.”
“I know I’m going to regret telling you this, but hearing you say that just made my night,” I replied bluntly. “That’s the most erotic thing a woman has ever said to me.”
She leaned forward and whispered, “Then I suppose this conversation is making you as aroused as I am.”
Just when the tension between us was at it’s peak, the waiter came and presented us with two chocolate desserts, which were heart-shaped for Valentine’s Day.
“These are complements of the owner,” the waiter informed us. “She says that it’s a real joy to see a couple so in love with each other regardless of their age difference.”
Elisha and I both looked over to see the owner sitting by the counter, a woman in her mid-50’s, smiling at us, thinking that we were an actual couple.
***
We headed home after we finished our desserts. I was a little disappointed that she chose not to continue our conversation on sex because of how tantalizing it had become. I knew it wasn’t normal by any means for someone to lust after someone like this, but I couldn’t help it. I saw her in a new light, one in which she had become the sexiest woman on Earth. But when we arrived home and got to our rooms, she picked up where we left off at the restaurant.
“Thank you for the wonderful night,” she said happily. “I had a lot of fun and it was nice doing something a little different between us. I just hope I didn’t get to carried away and made a fool of myself once again today by some of the things I was saying.”
“It was my pleasure,” I replied. “And no, you didn’t get carried away, or make a fool of yourself. Actually, that was probably the most interesting conversation I’ve ever had on a date.”
“You considered tonight a date?” she asked with her eyebrows raised.
“Well…you know what I mean…”
“I was just teasing you. It sure felt like a date between us didn’t it? And I still can’t get over how the owner of that restaurant thought we were actually together. How funny was that? It was fun playing along with it, but I don’t know if I could ever show my face there again.”
“I definitely can’t blame her for thinking that. You’re a very special woman and you can have any man you want. So why not a younger guy?”
She smiled and leaned forward to give me a soft kiss on the cheek.
“That’s for the complement and being such a gentleman. Good night.”
With that said, she turned around and headed towards her room, closing the door behind her. An hour had passed and I was just about to turn off the lights in my room and sleep, when I heard a soft knock on my door. It was Elisha of course. She wore her ivory colored silk pajamas, and by the serious look on her face, I couldn’t tell what she wanted.
“May I come in?” she asked quietly.
“Sure. What is it?” I replied, wondering why she came here so late.
She entered my room and said, “I just wanted to thank you for such a special night. You have no idea how much it meant to me. It’s been a while since I’ve connected with a man like that, and even though you’re my son, I still found it to be incredibly romantic. So, I want to show you my gratitude, and I won’t take ‘no’ for an answer.”
She leaned forward and planted a soft kiss on my lips. Then she wrapped her arms behind my neck and started kissing me full on the mouth. Her lips pressed tightly against mine, and I responded by doing the same. And when she slipped her tongue against mine, I did the same as well. It was a passionate kiss as if we were two people who were madly in love with each.
After a long moment, she ended the kiss and we looked each other in the eyes while we were face to face.
“That felt really nice. I enjoyed that,” I told her.
“Good, I’m glad you did. And I have something else you might like.”
My eyes turned towards her chest as she started undoing her top. Button by button her clothing was being undone, and it wasn’t long before the middle part of her braless chest was revealed. And after a few more buttons, her top was loose and she pulled it off and tossed it to the floor.
She stood completely topless before me. Her breasts looked stunning. They were fairly large and must have been c-cups. They were long and hung downwards, sagging a little, but the bottom of her breasts were perfectly shaped round globes. And to top it all off, she easily had the most impressive set of areolas and nipples that I had ever seen. They were large and brown, and her nipples started to stiffen as they were exposed to the air.
“These are yours tonight, you’ve earned them,” she said with a warm smile.
I didn’t reply, I didn’t need to. And it certainly was an opportunity I didn’t let go to waste as I bent down and began sucking on her large brown nipples. I used my hands to massage both of her firm breasts as I continued to suck, rolling each nipple around in my mouth, for both her pleasure and mine.
She briefly ran her hands across my hair and moaned before giving me a few pats on the back, signaling it was time for me to stop.
“It’s been a while since anyone has touched me like this. But I still have something else in mind for you. I want you to take your bottom off and lie down on the bed for me,” she commanded in a low voice.
“This isn’t the wine talking is it?” I asked. “The last thing I would ever want is for you to wake up tomorrow morning thinking that I took advantage of you. This isn’t worth ruining our relationship over.”
She smiled, “You’re so sweet, but no, this isn’t the wine talking. Well…maybe a little bit. Maybe the wine has given me the courage to do what I feel. And right now, I want to do this. I don’t care how wrong this is. But tonight, I need to feel a man between my fingers and lips.”
There was no point in debating this any longer. I was done with all the second guessing. So with a simple movement, I pulled my shorts and underwear down to my ankles and pushed them off of me, leaving me naked from the waist down. Under normal circumstances, the thought of her looking at my growing erection would have freaked me out, but this wasn’t a normal circumstance. I enjoyed that she was looking at me in this way.
When the novelty of Elisha looking at my penis wore off, I did as she requested and sat down on my bed, with my back leaning against the wall.
S
he followed suit and got on all fours, positioning herself right between my legs. I immediately noticed her soft breasts hang straight down from her chest. Her sagging breasts and big nipples were my favorite parts of her body. And to see them hang down the way they did, in that angle, only added to how erotic this moment was.
When she closed her eyes, it was time. She stuck her tongue out and gently pressed it against the sensitive head of my penis. It felt tingly and arousing, and it felt even better as her small licks grew to cover the entire length of my hard shaft.
After coating me with her saliva, she opened her mouth and took my hard cock between her lips and started sucking. It felt amazing as expected. But what made the whole thing even more surreal was how she suddenly opened her eyes looked straight at me while she sucked. Her face became gaunt and her checks hallowed as her vacuum like mouth intensified. Then slowly, her head started bobbing up and down. Her fingers made a similar motion as she displayed her talents when it comes to performing oral sex, making love to me with her mouth.
