The First TimebyHeyAll©
Everybody remembers their first sexual experience.
We can all remember the nerves we felt undressing in front of our partner. It feels like a line was being crossed that there's no coming back from, all for the sake of satisfying our sexual desires.
Unfortunately, not all first encounters are good. How can they be? It's a nervous and awkward situation.
Luckily, my mother and I were able to relieve our first experiences for the better- and with each other.
The First Time
My mother and I sat on the floor of our living room in front of the fireplace. It was a snowy night and we each had a cup of hot chocolate, and a lot of catching up to do.
I had just returned home from my first semester at college and she was eager to get as many new details about my personal life as she could.. My mother is one of those sentimental types who wears her heart on her sleeve. She's always been very open with me about her feelings, which shouldn't come as a surprise since she's a very open minded woman, and is a human sexuality professor at a local community college.
"So how have you been enjoying your college experience so far?" she asked. "Make any new friends?"
"Sure I have. I've met a lot of cool people. The whole thing about living with a roommate is kinda fun. But I have to admit, a part of me misses living at home where I have someone to cook for me and do my laundry."
My mother raised her eyebrow and gave me a stern look. "Is that all I'm good for?"
"That was a joke mom," I replied. "You know what I meant by that. It's just nice to feel a little more independent for a change when it comes to making my own decisions in life."
"Gosh, you've grown up so fast. It feels like only yesterday that I was picking you up from an after school sports practice. Now you're on your way to becoming your own man. I couldn't be prouder."
"Thanks. But don't worry though, it's not like I'm going to move very far after I graduate. You'll never be more than a short drive away."
She smiled, "So...are you dating anyone at your university? I want all of the juicy details if you are."
"Nah. Well, I wouldn't say dating, but there are a few girls I talk to here and there. Nothing serious since I'm always busy. I mean, you teach at a college, you know how the dating thing goes these days."
"I sure do," she replied. "Things are a lot different now than when I was growing up. Frankly, I prefer the old fashion way of how things went between a boy and a girl at your age. I'm a little more traditional in that regard."
I nodded, "Yeah, I know what you mean. There's nothing more attractive than a woman with class. But hey, I'm definitely not complaining if a girl is interested in doing stuff with me."
"Speaking of which, there's something I've been meaning to talk to you about. I should have said something months ago, but I was afraid of being that overbearing mother that kids often complain about."
"Sure. What is it?" I asked.
She paused for a moment. "Are you sexually active?"
"Really? Did my mother just ask me if I'm having sex? Mom, I'm a young adult. I know how to do things safely if that's what you're implying. You don't need to worry about a thing."
"That's a relief to hear," she replied in a reassuring tone. "You always were a smart guy, and I just wanted to reiterate the importance of doing everything safe. I've seen quite a few students get pregnant during college and it can be a real challenge for them to say the least."
"Well, thanks for caring. I've never thought of you as an 'overbearing mother' as you put it. You've always been really cool. Some of my friends have even commented about how awesome they think you are. As for the sex stuff, I'm always cautious and you're worrying too much."
"You're right," she nodded. "Young people your age are so advanced when it comes to sex. When I was growing up, people hardly knew what to do, or where to put things. I'm sure you were an expert from day one with all the information that's out there."
I winced, "Is that what you think? I know we're starting to drift into awkward territory here, but trust me, I was no expert when I started."
"The way you said that makes me think you have an entertaining story to tell."
"Jeez!" I said in utter surprise. "Talking about safe sex is one thing, but talking about this is just flat-out humiliating."
She smiled like nothing was wrong. "Oh come on. Studying human interaction and sexuality is what I do for a living. You aren't going to say anything that I haven't heard before. Besides, you always used to complain that I never treat you like an adult, well now here's your chance to have an adult conversation."
I gave her a skeptical look. "Fine. Well there isn't much to say. My first time was with my ex-girlfriend Anne."
"Anne huh? I figured it was with her. You two used to be so close and she was always flirtatious around you."
"Yeah, that's her all right. Anyway, after months of touching all the bases, we finally decided to take the plunge and have sex. We were both virgins at the time so it was obviously a big deal for us. Knowing what to do wasn't a problem since sex is all over tv and I've seen plenty of stuff online. But the thing is, when I put on the condom and started going at it, the whole thing felt so good that I came literally a minute or so after I started. Her tightness along with my excitement and nervousness isn't a very good combination for endurance. She even gave me a 'what the heck' look afterwards. So yeah, it was pretty embarrassing."
"That certainly does sound embarrassing for you," she replied, holding back her giggling.
"Well I'm glad you're getting a nice laugh from my least proudest moment in life."
"You're being too hard on yourself. You were a virgin, and lots of men have performance issues during their first time. Believe me, I've seen the statistics and have discussions with people about it. It's normal. And it's also understandable since men in general have far more pressure to perform than women do."
"I guess you're right," I nodded. "So what about you? What was your first time like? Was it as bad as mine, or worse?"
"That information is off limits mister," she replied in her motherly voice.
"Huh? Really? After what I just told you, you're telling me that you can't reciprocate and tell me an adult story of your own?"
She flashed a playful look. "It's different. I'm your mother. You aren't supposed to know about my sexual history."
"But don't you always say that it's a good thing to forgo traditional social norms in society?"
She raised an eyebrow, "Nice try, but I've always referred to female empowerment whenever I would mention that."
"Doesn't this count as female empowerment?" I asked. "By not telling your story, you're adhering to traditional social norms that women can't be as sexually liberated as men, and that a mother is expected to behave in a certain way based on the perceptions that society imposes on them."
"You're way too smart for your own good," she said playfully.
"Yeah, well I got that from you."
She took a deep breath, "Fair is fair I suppose. My embarrassing 'first time story' is slightly different than yours. When I lost my virginity to my then-boyfriend, it was a pretty standard event. There was nothing particularly embarrassing about it. Sure we were nervous, but it felt great and went on without any problems. But I suppose the awkwardness and embarrassing stuff came afterwards when I was learning about oral sex for the very first time."
My eyes widened. Hearing about your own mother having sex is one thing, but hearing her talk about giving oral sex is something else entirely.
"Oh..." I managed to respond.
She smiled, "You seem kind of shocked by me saying that. Is everything okay?"
"Uh...yeah. It is. You just caught me a little off guard, that's all."
"Seems that way. I'm sure it boggles your mind that a lifelong feminist and college professor had sucked a cock or two in her lifetime."
"That's exactly what I was just thinking to be honest," I replied nervously. "You practically took the words right out of my mouth...uh...I didn't mean it like that. What I meant was that I agree with what you just said."
She laughed, "And I'm sure the fact that your mother is admitting this is what's making you so nervous. I've never seen you like this before."
"That's because I've never heard you talk like this before. Plus sex is my favorite topic. The two don't usually mix."
"That's because the issues of sex and your mother aren't supposed to mix," she stated firmly.
"Maybe not," I conceded. "But I'd still love to hear the rest of your story. You've got my full attention."
"Well, I was 18 at the time. My boyfriend at the time was a pretty smart and charming guy, just like you. And he was also very handsome, just like you. We had sex only a few times and it was almost immediately that he started begging me to suck his cock."
"I love your new vocabulary mom," I joked. "You sound so much more like a regular person instead of an uptight college professor."
She smiled, "I'm just making sure you understand it. Anyway, oral sex was still something that was pretty taboo back then. I had never really heard of it, but I could imagine how good it must feel for him since he licked my vagina a few times before we had sex, and I thought it felt exquisite. The night before I finally agreed to do it, my best friend told me about her experience with it, and how it didn't taste that bad. She had a lot of nice things to say about it in general."
"And was it what you expected?"
"It was interesting," she said. "The first time I performed fellatio on him was after prom night. We drove off to a secluded area on the coast and he placed a picnic blanket on the floor by his car. He leaned against his car door, and I got on my knees and basically did what he told me to do, along with advice from my friend. Honestly, it felt a bit degrading and a humiliating to a certain degree. But at the same time, I loved that he was getting so much pleasure out of it."
"Well that doesn't sound so bad," I noted. "That sounds like the typical first time with oral sex for anyone. I thought you were going to tell me an embarrassing story or something."
"That wasn't the embarrassing part. Since we were both 18 when I started to suck him off, he naturally got to the orgasm stage very quickly. I could tell that he was about to finish, so I closed my eyes and got ready to swallow, which is what we had previously agreed on. Keep in mind that personal grooming isn't the same as it is now, and his pubic hairs kept tickling my nose. By the time he released his fairly large orgasm, I sneezed and there was cum everywhere. And I mean everywhere. It was all over his legs and pants. I chickened out when it came to putting it back in my mouth and so it continued squirting on my face and my expense dress that my dad paid for."
"Yikes. That does sound pretty bad. Now my story doesn't sound so bad in comparison."
She raised an eyebrow, "It didn't end there. The ride home was quiet and awkward. My curfew was fast approaching and the stains on my dress were practically impossible to remove since we didn't have anything except dry tissue paper to use for clean up. I went back home with a plan to basically run to my bedroom before my parents would have a chance to try and talk to me. The best case scenario that I had hoped for would be that they were already asleep."
"I'm assuming things didn't go the way you expected it to."
"Nope," she replied, shaking her head. "They were wide awake and stopped me at the door for every single detail. They were so proud of me and they cherished the fact that I was becoming a grown up. It was nerve wrecking for me to stand there knowing what I knew. My dad definitely didn't notice. But I saw my mom glance down at my dress a few times with a mortified look on her face. She clearly knew that there were faint cum stains all over her little girl's prom dress. It was horrible. I went to my room afterwards and crawled underneath my blanket for the rest of the night. Luckily for me she never brought it up or lectured me about it."
"Holy crap that's embarrassing," I said, wanting to laugh. "That just might be one of the most hilarious sex stories I've heard in a long time. I don't think I'll ever be able to look at grandma again and not think of what you just said."
"I'm glad one of us is getting enjoyment out of that," she sarcastically stated.
"So am I. And I'm probably going to regret saying this, but hearing that was actually kind of arousing in a weird way. I don't know. It's not everyday that you get to hear a sex story in that kind of detail."
Her eyes looked down at my shorts. "Your body part is doing a pretty good job of showing me that."
"Ugh...It's a natural reaction. Sorry mom.," I replied, reaching down to adjust myself.
"Don't be," she smiled. "It was my fault for telling you about it and for bringing up this topic to begin with. I should have known you'd be aroused since you've been spying on me sunbathing in the backyard for years."
I was absolutely dumbfounded when my mother brought up my old voyeuristic habits. I wanted to deny it. I wanted to pretend like she was just teasing me. But there was no way out of it.
"So....you knew about that all this time?" I asked.
She nodded. "Of course I knew. I'm your mother. It's my job to know these things. You would be surprised to find out how much moms know about their sons."
"I probably would be," I acknowledged. "For what it's worth, you look great in a bikini, and you were the first woman I've ever seen in that way. It was something I hadn't seen before. So I hope you don't think I'm creepy or anything for having a look. I was curious."
"You really have nothing to be ashamed about. It's normal, and it's something that's becoming more widely acknowledged in the studies of human sexuality. All you have to do is look at the popularity of mother/son related stories on the internet to understand that it has a growing audience."
"So basically, you look at erotic story porn?" I said light-heartedly.
She flashed me that stern motherly look. "I was doing research mister. And I don't know why you're making jokes about me young man, I'm not the one spying on family members."
"That was harsh."
"But true," she quipped. "I've told you so much more about me, than you did about yourself. So why don't you enlightenment on all this?"
I winced, "You've got to be kidding me. This is kind of more embarrassing than us sharing sex stories. Actually, it's a different league of humiliation. Let's just call it a night and go to bed while we're on a high note."
"Nope. I want to hear about your first time fantasizing about me. I promise I won't judge. And I want all of the juicy details."
I took a deep breath. "Alright already. This isn't something I planned on ever telling you, but fine. It started a few years ago right after that Christmas party at our house."
"Let me guess. Was it the night that I had too much wine? I vaguely remember waking up in my room feeling a little exposed."
"That was the day. You wore a really sexy Mrs. Santa outfit that night and it was the first time I had ever checked out your legs in that bright red skirt you wore. I felt kind of ashamed about it, but you looked great. After everyone left, you went to your room and practically collapsed on your bed. When I walked passed your room, your door was slightly open, and I peeked inside and saw you touching yourself. And by that I mean your panties were around your knees and you were really going at it with your eyes closed. It was the first time I had ever seen a woman's private body part in real life, and that was the first night I had ever thought about you in that way."
"So that makes tomorrow the anniversary of when you started fantasizing about me," she said with an understanding tone.
"Pretty much. I thought that would be the end of it, but once summer came and you went swimming and tanning in the backyard...I couldn't resist anymore..."
"There's nothing to be ashamed about. It's natural. It's also somewhat inevitable since we both live in the same house, and we were both bound to eventually see things that would make us curious."
"Thanks for being so cool about it mom," I replied. "A friend of mine got caught spying on his mother, and he was practically grounded for weeks. She really threw a fit over the whole thing. Poor guy never recovered from it."
She smiled, "Well, some mothers aren't as open about the workings of human sexuality as I am. But the ones that are realize that it's not such a dirty thing. Being perfectly honest here, I'll admit that I knew you were watching me tan in the backyard a few times, and I thought it would be cute to change my tops while you watched, just to see your reaction when I came back inside the house."
"Really? Jeez, you really are a cool mom."
"Thanks," she replied happily. "No harm, no foul- right? I didn't see any harm in that. Just keep this between us. I don't want anyone knowing."
"Right. I'm not going to tell. Believe me, I don't want people knowing about this any more than you do."
She looked over at the clock. "It's getting late. Let's go to bed, we've got a big day tomorrow with our Christmas party . I don't know about you, but I'm going to dream about a much happier ending to my 'first time' story. It's not like we can redo any of it in real life."
"Who says we can't?" I blurted out.
For a moment there was nothing but pure silence between us. We had both immediately realized the meaning of what I said, even though it slipped out by accident. She gave me a serious look that I had never seen before, and I hoped that she would eventually take it as a joke.
"Is that what you want?" she asked expressionlessly. "You want a do-over with me?"
I paused for a moment and tried to think of reasonable response.
"That just slipped out. I was trying to make a joke."
Her eyebrow raised. "I know you well enough to know when you're trying to make a joke, and when you say things without thinking. Does a part of you still have sexual feelings for me?"
My heart rate picked up and my nerves started to take over.
"A little," I admitted. "I mean, you don't have to worry about me being a weird pervert or anything. But let's face facts, you're really beautiful."
"How about when you lost your virginity? Did you think about me then also?"
"Okay, now we're headed towards uncomfortable territory if we weren't already."
My mother then leaned forward and gave me a soft kiss on the lips. It was a gentle touch at first, but each kiss became harder and more forceful. She kissed me the way any other woman would, but the fact that it was from my own mother made things so much more arousing.
"Now are you ready to talk?" she asked after ending the kiss. "Did you think about me when you lost your virginity?"
At that point, I was extremely turned-on and had nothing left to hide.
"I did. I'll admit it. Part of the reason I came so fast is because I imagined I was screwing you. There, I said it. It's something I had wanted to do since that Christmas night I saw you fingering yourself."
She paused for a moment. "For the first time in my life, I'm actually speechless. Hearing those words coming out of your mouth is supposed to be every mother's worst maternal nightmare."
"But not for you?"
"No," she said, shaking her head. "It's an enjoyable fantasy to be honest. I love the taboo and the unusual attraction. Why not? There's no harm. It's just a silly fantasy."
I nodded. "You've got that right. Who cares what society says about this...not that I plan on telling anyone."