Teen Turns: Boyfriend’s Mombysilkstockingslover©
Note 1: This is based on an idea by Hernandez1983.
Note 2: Thanks to TexBeethoven, Robert, David, goamz86, and Wayne for editing this story.
PS: The concept of 'turning' doesn't mean a girl or a guy instantly goes gay... but it does mean they will discover another area of their sexuality they didn't know existed.
Teen Turns: Boyfriend's Mom
Dating Josh had been going pretty well.
He was sweet, good looking, funny, and respected that although I had turned eighteen a couple weeks ago, I still wasn't ready for sex.
My parents had lost their virginities together on their wedding night, and so had all four of my grandparents. I hadn't been there, of course, but I had it on good authority... often accompanied by finger wagging to emphasise just how important those facts were. Now I wasn't unduly swayed by the finger wagging and wasn't purposely waiting for marriage... nor was I under any delusions that I may be the only eighteen year old virgin in the state... but I did want to make sure my first time was special and with someone I loved... and Josh seemed to be that person... and dear God, I didn't want to turn out like my parents who had split up when I was two and still resented each other for the mistake they had made 18 years ago.
Although we were taking it slow, I had given him a hand job at the drive-in, and had sucked on his penis a bit the last two times we'd gone out. The first time it was for maybe two minutes before I gagged on it... but the second time I lasted longer... although I could only take a little more than half of his six inch penis in my mouth (but I was determined to get better and since then had practised with a carrot for several days and was considering upgrading to a cucumber).
He had felt me up many times, he really loved playing with my big breasts, although I had not let him actually see them yet.
Maybe I was a prude, but I just wasn't comfortable with being naked in front of him or anyone else.
Truth be told, this reticence was more about insecurity than anything else. I had been teased very cruelly by the other girls for developing early (grade six). I was apparently the first weirdo in the entire universe to develop breasts, and even now they were abnormally large for my slender frame.
I moved to Wakefield in my junior year, and since I no longer had to endure the torture that was called physical education (no actual education happened, just a social hierarchy based on strength and coordination... of which I had neither) in this new school I was able to wear baggy sweaters to hide the embarrassing breasts that nobody here was quite aware of.
Josh was awesome. We liked the same music, both of us loving 80s retro, we were both advanced students and both were in band. He was thoughtful, funny and caring... I was pretty sure I was beginning to fall in love with him... and was already considering giving up my virginity to him... soon... but not yet.
And although I wasn't ready for sex with Josh just yet, I was extremely sexually curious and masturbated a lot to online porn and erotic literature. And according to what I'd read (video porn doesn't count, since all those guys have horse dicks), Josh was above average in the penis department... I guessed about six inches. So when the time came (unintended pun), I was expecting to really come. I had used my fingers, hairbrush and an empty collectable coke bottle from the 80s (that one broke my hymen) and I already wanted something bigger and fleshier.
Anyway, I had met Josh's mom and was in awe of her. She was beautiful, sweet, and almost excessively friendly. She complimented me profusely about how pretty I was and even suggested we go to a spa together.
My own mother blamed me for her horrible life. Although she almost never said as much, she constantly implied it by her words (or lack of words) and her uncaring behaviour. So I was very drawn to this new motherly figure who actually seemed to care about me. So I eagerly agreed to a spa day, although I had only the vaguest notion of what that might be.
The massage was first, and we were lying side by side waiting for our masseuses, which I found strange, but was too shy to mention.
The towel I was wearing was insufficient to disguise the size of my breasts, and it didn't take long for Mrs. Walker to notice.
"Oh my, where have you been hiding those?" she asked, boldly reaching out and actually feeling me up!
My eyes went very wide, and I was paralyzed with shock as I thought to myself, 'Is Mrs. Walker, my English teacher and my boyfriend's mother, really feeling me up?'
She continued speaking casually, as if her hands and my breasts weren't separated only by a thin towel, "These beauties are nice and firm. Very impressive for their size."
"Uh, thanks," I said, not sure what else to say. This wasn't quite sexual, although she was paying them rapt attention, assessing them physically, and cupping and squeezing them... oddly with the same fascination that her son often did.
Removing her hands a moment later, she pulled her own towel away and tossed it in a corner. I was suddenly facing my boyfriend's mother naked! "Do mine seem to sag at all?"
"No, Mrs. Walker," I answered. Her breasts were slightly smaller than mine, but still impressively firm for a woman in her forties. My mom had big tits like mine, and they sagged disgustingly now... a fate I hoped to avoid by staying in great shape. I even added, trying to keep my cool during this strange encounter, "I hope mine look that good when I'm older."
"Please, Janelle, call me Selina. 'Mrs. Walker' makes me feel so damn old," she offered as she reached for my hands.
As I went to agree, I suddenly discovered I was grasping two handfuls of bare breasts. I was a bit confused, but I was pretty sure I hadn't placed them there myself.
I stammered, having never touched a pair of breasts other than my own, "S-s-sure, Selina."
"Do they feel firm?" she asked, holding my wrists in place so I had no choice about feeling her up. "That's as important as how they look."
Bewildered, I agreed, as I squeezed them, in awe of them, "Yes Selina, they're perfectly firm."
"Thank you, Janelle," she smiled, letting go of my wrists. "I needed to hear that."
Oddly, maybe out of utter paralysis but maybe not, my hands remained on her breasts, gently squeezing and caressing them for about ten more seconds, before I realised what I was doing and pulled them away. She had made no move to hasten me away.
My face burned red, feeling like I had just been involved in an act of lesbianism. But it progressed to crimson when I glanced down and saw that her vagina was completely shaved.
I quickly looked back up, but it was too late. I was busted. "It's important to keep your nether regions bare," she explained. "Vaginal hygiene is critically important."
"Oh," was all I could say as the awkward situation became even more awkward.
"Let me see your vagina, my dear," she requested.
"I'm not really comfortable with that, Selina," I refused, wishing the masseuses would show up.
She ignored my protest and obvious discomfort and insistently snatched the towel away from me. She explained, "Janelle, we are both women. We have the same body parts; there is no reason to be shy."
Overwhelmed and shocked, I stood there as she studied my body very thoroughly.
"Your breasts really are amazing," she complimented, looking at them as if she were a jeweler appraising two fine diamonds, before looking down at my hairy vagina. "Oh my, we will need to do something about that, though."
Before I could respond, although I was speechless and wasn't sure what I would have stammered if given the opportunity, the two masseuses walked into the room.
I quickly grabbed the towel on the bed and covered myself, feeling again as if I was caught in the act of lesbianism.
Selina simply walked over to a bed, not at all uncomfortable to be completely naked in front of two strangers.
I quickly moved onto the other bed and hid myself under the sheet of safety, still trying to comprehend the surreal encounter that had just occurred.
Throughout the entire quiet massage, which felt utterly amazing and relaxing, I tried unsuccessfully to make sense of that strange encounter.
The rest of the afternoon passed without anything else out of the ordinary as we got scalp massages, manicures and pedicures, and haircuts while we chatted about school, Josh, and holiday locations she had been to and that I wanted to go to when I was older.
I noticed that when she talked, she was often touchy feely, either with the hairdresser or with me, when we were sitting beside each other for our pedicures.
The more we chatted, the more I came to the conclusion that my brief feeling up at the beginning was just Selina being Selina: friendly and touchy feely.
On the way home, she suggested, giving my leg a squeeze, "I want you to come over on Saturday for supper."
"Okay, that would be great," I agreed, oddly captivated by her and her motherly attentions... she was all the things that my mother wasn't.
A few days later, I arrived for supper dressed up in a cute sundress and pantyhose. I had noticed that every time I saw Mrs. Walker she was in a dress or skirt and pantyhose that looked very good on her. I felt a need to emulate her.
And truth be told, I wanted to impress her.
I had also, although I had done it awkwardly, and despite it not being something she would ever have the chance to discover, shaved my vagina. It had taken forever and I was terrified the entire time that I would cut myself, but I did it... as a special surprise for Josh on the day I would finally allow myself to give him my virginity, and also as an expression of my secret desire to be more like Selina.
When I arrived, she was indeed wearing a dress. A nice black one that didn't camouflage her large breasts at all. She pulled me in for a big hug, our breasts squeezing together, as she complimented, "You look utterly delicious."
I thought the word 'delicious' was strange, but parroted back, "You look delicious too."
As she broke the embrace she smiled, her tone oddly sultry, "Oh trust me Janelle, I'm a taste treat to die for."
I laughed, unsure what she was meaning, "I imagine so."
She looked down at my feet. I had taken off my heels as soon as I walked into the house, since she had a no shoes rule, and said admiringly, "Pantyhose. Classy."
"Thank you," I nodded, before adding, wanting her to know I was trying to emulate her, "I'm trying to learn elegance from you."
"You are? In that case come with me," she said, taking my hand and leading me to her bedroom.
I was confused, but I followed. She then ordered, "Wait here."
"Okay," I agreed, having no idea what she had in mind.
She went to her dresser, shuffled through it for a bit, then returned with nylons in her hand.
"Hold these," she ordered, handing them to me.
"Okay," I obeyed. I watched in shocked awe as she dropped to her knees in front of me, reached under my dress and pulled down my pantyhose.
She explained, acting as if her intimacies were perfectly normal, "Reinforced pantyhose are what grannies wear."
Although I was bewildered by her advances, I cooperated and lifted up my legs, one at a time, so she could pull the pantyhose off me.
She got up, tossed them in the waste-basket, and ordered, "Sit on the edge of my bed, my dear."
Although everything about this was unorthodox, I was compelled to obey, as if she were my very own Fairy Godmother... creating a new, sexy me. I looked around for singing mice, but didn't see any.
I hopped onto her bed and she returned to me. She took the pantyhose back from me. I suddenly learned they were not actually pantyhose... but very elegant, very sheer, very luxurious thigh high stockings.
I remained in silent shock and awe as she again dropped to her knees, and began rolling a stocking up my leg.
She explained, "These are expensive, but sexy as hell and so silky sheer."
"Oh," was all I could muster. The silk gliding up my leg felt so nice.
Weird... but oh so nice.
She stood up, lifted my leg up, so high that my covered pussy (my covered, shaved pussy) was suddenly in full view for her, as she finished rolling up the stocking.
"Apparently you need new panties too," she said, noticing my cheap Walmart panties... light blue and cotton bland.
Yet again surprising me, she reached up and ordered, "Lift up, sweetie."
I again complied, my mind in confused, unquestioning, obedience mode, as she tugged my panties down my legs.
"You shaved," she noticed, "Very nice. Sweetness, you have a very ripe, juicy looking pussy. I'm so glad she's decided to leave the forest and come out into the light of day."
I could find no response to the strangest compliment I had ever received. I was speechless from this whole ordeal, yet oddly my pussy was wet.
"We'll have to take you garment shopping ASAP," she declared, as she walked away and tossed another piece of my clothing into the waste-basket, as I sat at the edge of her bed wearing no panties and only one stocking. Talk about surreal! I looked around for Salvador Dali, but didn't see him either.
She returned, dropped back to her knees and slowly glided the second stocking up my other leg.
She again lifted my leg up to finish smoothing the stocking and repeated, as she gazed openly between my legs, her tone somehow different this time, "Yep, such a ripe, juicy pussy."
She let go of my leg and went back to her dresser.
She returned a minute later with what was definitely not my typical underwear.
"Stand up," she ordered, as she dropped to her knees in front of me for the fourth time.
I obeyed for the umpteenth time. I didn't know why I was complying with her every request, but it seemed... somehow 'comfortable' was the perfect word.
I robotically lifted my right foot, then my left foot, so she could adorn me with what was obviously a thong. Does anybody outside of Las Vegas ever wear thongs? Apparently so.
Although we weren't anywhere near Las Vegas, she then slowly slid the thong up my sheer stocking-clad legs, her warm breath every so lightly tickling my pussy, sending a chill through my entire body, and approved, "This is so much better, my dear."
"Thank you," I responded, actually feeling sexier in the strange lingerie.
"You are a sexy young woman, Janelle," she complimented, standing in front of me. "It's time to stop hiding."
"Yes, ma'am," I nodded, basking in these many compliments that I never got from my own mother.
"And none of this ma'am stuff," she scolded. "I'm Selina."
"Sorry, of course," I nodded, as she took my hand and led me back to the living room.
Once back in the living room, she led me to the dinner table and patted a seat, "You will sit here beside me."
"Oh, okay," I nodded, before asking, "Can I help with anything?"
"Not right now," she smiled, before adding with a playful tone, "but remember that question for later."
"Okay," I nodded, having no idea what she meant. She walked into the kitchen.
Josh came up from behind me seconds later and startled me.
He complimented me like he often did, even more so since my makeover, before giving me a kiss. He asked, "Why are you wearing a dress?"
"Just trying to get into your mother's good graces," I answered.
"She already says you're delicious. Just be yourself," Josh advised.
I nodded, perplexed at hearing the word 'delicious' again, and trying to flirt, "Plus, I also wanted to look good for this handsome guy I know."
"Who is he?" Josh joked, putting his dukes up.
"I think you know him," I smiled, playing along.
"I'll kill him," he said, starting to shadow box.
"Please don't do that, you big bruiser," I smiled. "I think he may be a keeper." I leaned in and kissed him again, enjoying our playful banter.
The kiss was interrupted by Selina who said, "No hanky-panky at the table, you two."
"Oh, Mom," Josh said, breaking the kiss. "This isn't the 1950s anymore."
"Do you think I was alive in the 1950s?" She questioned, her tone suddenly insulted.
"I was kidding," Josh said, before adding, unable to control himself, "I know you're a sixties child."
"Janelle, you may be a widow before you're married," she joked.
"Mom!" Josh exclaimed.
Selina responded, able to give as much as she took, "You'll never do better than Janelle here. I can't even fathom why she is dating you, she could obviously do so much better."
"Mom!" Josh repeated.
I added, "Yeah, Josh, you better shape up or ship out."
"Not both of you," he sighed, protectively covering his head with his arms, abandoning any offense in favour of defence, signaling that he had been overpowered by overwhelming odds.
"We're like a double-barrelled shotgun," Selina joked, "so you'd better be a good boy. Now take a seat; dinner is ready."
"Yes, Mom," he nodded, submissively taking a seat as Selina disappeared back into the kitchen.
I took a seat opposite from him, where she had earlier instructed me, finding the placement of our seats very odd.
There were two chairs adjacent to each other on one of the table's long sides, one chair on the other long side, but none at either end. I was across from Josh, and Selina was next to me.
Selina, like the mom of the year she was, brought out the meals. Her husband, having learned he was gay, had left her two years ago, so she was now a single mom. She was obviously not thinking about her ex as she gave me a dazzling smile before sitting down to join us.
The three of us chatted throughout dinner, Selina squeezing my arm three times (yes I was counting) as she asked me questions or pelted her son with playful condemnations. She joked that it was nice to have more estrogen than testosterone for once, before her hand gave my leg squeeze number four as we agreed that Josh needed a haircut before the prom... but this time her hand remained on my leg.
She asked a moment later, "Josh, could you be a dear and go get me another glass of wine?"
"Sure, Mom," he nodded, getting up and asking me like the gentleman he was, "Can I get you anything, Janelle?"
"I'm okay," I answered, as Selina traced her fingers up and down my knee up to the hem of my dress.
Once he was gone, Selina asked, "Do you like how silky these nylons are?"
"Yes, they are super soft," I concurred, again finding the situation awkward, but not feeling daring enough to say so.
She took my hand and placed it on her own leg. "They feel even better when you touch them on someone else's leg."
"You're right," I agreed, the sheer nylon feeling sexy and soft on her legs, my fingers enjoying the silkiness and soft warmth of her thigh but not in control, as she moved my wrist up and down slowly.
"I'm always right," she joked, just as Josh returned with a glass of wine.
I quickly pulled my hand away, as if I had been caught cheating, but she didn't... her hand remained resting on my leg.
Not at all deterred by my boyfriend's presence, she gave my leg a firm squeeze... as if speaking to me through touch... although this was a language brand new to me. I was far from fluent.
We resumed chatting, but I was constantly distracted by Selina's hand on my leg. It seemed to be creeping ever so slowly up my leg, now noticeably beyond where the hem of my dress had originally been.
Josh asked, "Are you okay, Janelle? You look flushed."
"Oh, oh, I'm fine," I stammered, just as Selina shocked me by placing a finger directly on my barely covered pussy and boldly tracing my pussy lips.
"You sure?" he asked, looking concerned.
"Yessssss," I trembled, as her finger slipped smoothly inside me, and my head spun with shock. All the other moments I had dismissed as strange but innocent, had not been innocent at all.