All those mentioned within this story are over the age of eighteen. A special thanks to linda1234 for her encouragement, and of course to Staci, who I love and adore. Mwah!
It was the summer between what would typically be my college junior and senior years, but in reality I was less than a semester away from graduating. I had my sights set on my post-graduate degree, but was smart enough to know another year-and-a-half to two years of tuition was really going to put me in a deep financial hole before I’d even entered the workforce.
I’d seen a number of stories on women becoming sugar babies for successful men, and being one who enjoyed good sex from an attentive lover – actually, I’m sure anyone who knows me would call me a highly sexual individual – I thought it might be fun work, as it were. And the college guys I’d spent time with, while not jerks by any means, weren’t the most attentive when it came to sharing pleasure. I’m a big believer in shared pleasure, and like to think I give as good as I get. So after a lot of thought on the moral implications, I determined I’d like to be compensated for the time I was going to spend with successful gentlemen. At least I hoped I’d find some successful ones!
What led me to do such a thing? Prostitute myself? I won’t bore you with the “we’re all prostitutes in one way or another” argument, but I was comfortable, even excited with my decision. I love having sex, so why not be compensated monetarily for my time? Just how did I get to this point in my life? I guess it was during high school when my sexual journey began. While I’d kissed a number of boys, and let them play with my then-smaller boobs, felt their hard-ons and let them rub up against me, my first true sexual experience was with an older woman.
Shelly was a young wife, no kids at the time, who lived next door to a couple I used to babysit for, on the next block over from my house. She had very pretty, almost flawless skin, light brown hair, and large, but soft looking brown eyes. Being medium build, she may have been 5’6″, with a 34B, sometimes a little fuller breast size.
We had talked a few times, just girl stuff. I don’t know if I was mature for my age, or was simply flattered an older woman wanted to spend time talking with me, but we seemed to get along well from the very beginning. I just knew I felt comfortable being with her.
Then one day, during the summer and a few weeks before school began, I happened to be walking by when Shelly invited me in. We were sitting in her kitchen talking and drinking cokes, and before long found ourselves talking about boys. She asked me how far I’d gone with any of them and I told her it was mostly just kissing, but they did want to touch me in other places. During this part of our conversation Shelly had placed her hand on mine, and as I spoke she would slowly and softly rub her gentle hand up and down my arm, just from the wrist to elbow. Again, I don’t know if it was something that drew me to her, but I didn’t seem to mind the touches. It actually felt quite nice, maybe just mild tingles?
She then asked me if I thought I was a good kisser. I said I thought so, and she asked if I would like to show her. Again, for some reason, maybe just my young bold nature, but I didn’t hesitate at all when she asked.
While I might not have been as good as I thought when I arrived, by the time I left for home that afternoon she taught me the art of kissing, and how to use my lips, tongue and fingertips. I learned to listen to the sounds a person makes, their body movements, how those were clues and how I should respond.
But we just kissed, a lot, that first day. And honestly, she had me all worked up so once I made it home I had to touch myself until I climaxed.
She had invited me to come back a couple of days later, and boldly asked me what I’d done when I left. The dirty girl in me wanted to tell her, she just had that kind of spell over me. Shelly knew what she was doing that first day, and when I told her what I’d done once I’d gotten home, she asked me how long I’d been masturbating. After I told her maybe a couple of years, she asked if I’d like for her to show me how it was done? Properly was the term she used. She said we wouldn’t touch each other “down there”, just ourselves.
Taking my hand, she led me to her bedroom and began undressing me. And we kissed, a lot. That woman loved to kiss and use her lips, which she did on the upper part of my body – my neck, behind the ear, all over my face, shoulders, Once we were both nude she had me lay up against the headboard while she did the same against their footboard. Facing each other, with only calves, ankles and feet touching, I mirrored her movements as she showed me how she made herself orgasm, how she took her time, running over and around her mound, then sliding a finger, sometimes more than one, up and down her vagina, caressing the outside, dipping inside, bringing her juices back up to her clit. She explained each porno woman was unique so I might reach my orgasm differently.
I had tasted myself before, first just out of curiousity, and was okay with it so it was not a shock when Shelly offered me her fingers after our orgasms. Naturally, she tasted different, but certainly not unpleasant, and in fact had a touch of sweetness to her. And then we kissed. A lot, which we both now seemed to like very much, along with the warm, gentle hugs and caresses. Needless to say, it was very intense while being oh so sensual. She had to remind me a number of times to slow down, and enjoy the pleasure, and there was more to masturbation than just rubbing my clitty. How watching someone pleasure themselves could be pleasurable in itself, and how just looking into your partner’s eyes could heighten the experience.
I was too naive to realize everything we’d done up to that point had been foreplay. She had seduced me over a week’s time, Lord that woman had patience. She was a very good lover-teacher. But then, I later thought to myself, she has a husband, and he must be having a lot of fun at night. Strangely, as I look back we never really spoke much about him, and certainly never put on a show. My, I couldn’t do something like that back then.
It wasn’t until the next week that Shelly first kissed my kitty, and we made love for the first time. My body felt both as if it were on fire, and being mildly electrocuted, the little shocks seemed to be racing all through me, and not just in my pussy, but all over. It was such a contradiction, with both warming waves and also tension-filled pulses, seemingly from my stomach, outward. And I’d never been so wet.
Shelly’s lips and tongue played me like a musical instrument, dipping here, swirling there, gently sucking everywhere. And while she kept saying to me “Shhh, shhhh,” I found the verbal release made everything a little more intense, and pleasurable. Her finger gently rolling over my slickened anus, and then into my pussy sent me over the edge, and I must have looked like a fish flopping around on her bed. I’d thought I’d made myself orgasm before that day, it was nothing compared to what she did for me.
When I finally made love to her, I was overwhelmed with emotion, and wanted so badly to please her as she had done with me. Shelly was so patient with me, reminding me how it felt when she made love to me, and to listen to her body. I literally made love to her treasure with my mouth and tongue, I could not get enough of the reward whenever her juices began flowing, knowing I’d done something good. Her lips so soft, her little bud so hard, yet delicate. I cried when she came, and was lucky enough to bring her to at least one more orgasm before I was emotionally spent. But there was almost a majestic feeling of accomplishment watching her receive the same ecstasy she had given me.
She hugged and soothed me, kissing my salty tears and her fluids from my face as we bathed in each others’ warmth for what seemed like hours, but was probably less than one hour in actuality. Our sessions went on, on a not so regular basis, pretty much all summer. And each time we’d be done before her husband came home from work.
I did see her on and off during my senior year, and was never really attracted to any of my female classmates, and it may have just been my imagination but the boys seemed to be more interested in me that year. Was it a self confidence I was beginning to feel? Something Shelly had nurtured over the summer? Whatever it was, I was looking forward to getting close with Jason, one of my classmates. I’d shared my feelings with Shelly, and we discussed how sex with a male might go that first time, and soon agreed it be best if I was “prepared” to give myself to him.
Because of the love I felt with Shelly I told her I wanted her to take my virginity, and we agreed one weekend to get together when her husband would be away with friends. Prior to our “deflowering date,” , I had personal experience with a couple of Shelly’s smaller toys. But for this occasion Shelly had purchased a strap-on, with what appeared to be a medium-sized dildo installed in the harness. From my limited experience with the male cock, and with only pictures and videos as examples, it appeared and felt life-like, firm yet flexible and much smaller than those belonging to porn actors.
Shelly said we should try to imagine how Jason and I would make love. She said I should insist on it happening in either his or my bedroom when we could get some time alone, and to definitely say no to any attempt to fuck in his car. that, she told me to sit on the bed and wait for her to return, before she stepped in the bathroom. When she came out moments later she was dressed in slacks and an untucked blouse that laughably tried to hide the dildo she was wearing underneath. There was a large protrusion that appeared to be sticking up in the pant’s waistband, that caused me to start laughing.
“Okay, anime porno it might not be this prominent in actuality, but with your looks, body and mannerisms, this is the type of affect you’ll have on men for a very long time. But for the time being, just go with it,” Shelly stated. “Now, come over here.”
I stood and she held out her arms as she moved towards me, firmly grasped my head and began kissing me a bit more aggressively than she’d done in the past. I was caught a little off guard at first, but quickly began to respond in our usual amorous way.
Shelly paused and explained, “Boys, and men, will typically be more eager and frisky than you may be used to with a woman. It’s not unusual and most women like that, as long as they’re respectful of your feelings, and don’t hurt you. Make sure you let them know what’s acceptable and what’s not. You are not their plaything to be used as they see fit, you’re someone who’s seeking and wanting to share your pleasure with another. Do you understand?”
Taking a moment to absorb everything she said, I then replied with a, “Mmm hmm,” before ardently returning to our kissing. I think my boldness surprised her a little, but soon we re-engaged in our impassioned activities. Shelly began feeling every inch of my clothed upper body while alternately kissing my face and neck. Then she began to pull my shirt over my head and removed my bra, exposing my breasts to both the cool air and warm touch of her hands, firmly manipulating my orbs and nipples.
Bringing her hands up to my shoulders, she then said, “Please take my pants off lover,” as she began pushing me down in front of her.
I started to unfasten her slacks and pulled down the zipper, feeling the cock’s hardness against the back of my hands and fingers. Sliding her slacks down I could see the outline of the dildo and harness inside some granny panties I’d never seen her wear, and tried to stifle a giggle.
“Never laugh, or indicate any type of disappointment when your down there with a man,” she admonished, “or your evening will be over before it really begins. Some men are show-ers, some are grow-ers, and for some it’s a sensitive subject. Be respectful, and if things don’t turn out as planned in the end, then just move on and find someone who will satisfy you.”
“I understand,” I replied, “but I was laughing at your panties.”
Shelly then sighed before saying, “Okay. But also remember not everything will go smoothly during those moments of passion. There will be awkward moments and slip ups…even slip-ins and outs, if you know what I mean. It’s all part of the learning process, and there’ll be moments of embarrassment for both of you. The most important thing to do it to be attentive but have fun. You can both laugh about it afterwards.”
I nodded my head as I was looking up at her, my thumbs still in her panty waistband.
“Now, take my underwear off, and play with my cock,” she commanded.
I should have slowly removed them instead of quickly yanking her panties down, because the next thing I knew I was hit in the top right side of my head with a plastic cock. And it hurt. It was Shelly’s turn to laugh and softly shake her head, but soon returned to her role as my lover.
“Feel how hard you’ve made me,” she instructed, “rub it over your face, run your tongue up and down my shaft and over the head. Yes, just like that. Now put it in your mouth, yes it feels so good. Swirl your tongue around the head.”
This went on for a few moments before she said, “That’s great lover, yes take me deeper. Mmmm, yes. So good. Now play with my balls.”
At this point I stopped bobbing my head, and with half of a fake cock in my mouth I looked up with raised eyebrows and murmured, “Hmmm?”
“Take my balls in you hand and gently roll and squeeze them. Play with them,” Shelly said.
I then understood she was saying this is what I should do when I was with Jason, but I also didn’t want to ignore her either so I began running my fingers over her pussy, up and down her now-dampened slit, and then into her slippery channel. I began to slowly finger fuck her, occasionally using my well-lubed finger to glide over and around her clit, while also trying to concentrate on the hard cock in my mouth as I felt my jaw begin to ache.
At this point Shelly had started to nominally buck her hips in unison with my finger movements, tenderly driving more of “her” cock into my mouth to the point where I was nearly gagging.
“Fuck that feels good!” Shelly nearly shouted. “Too soon to cum. Too soon,” she said as she withdrew the cock from my mouth, and my finger from her pussy, while I caught my breath.
“Up on the bed baby, it’s time to fuck. Yes, right there in the middle. Now lay back and spread those long, beautiful legs.”
Shelly moved onto the bed as well, and began slowly crawling up between my legs.
“Oh yes, look how wet that pussy is, just waiting to be fucked. You’re a good little arap porno cocksucker aren’t you, baby. Yeah, you enjoy sucking cock don’t you, you little minx. Your pussy is saying yes. Mmmm, let me have a little taste of that sweet thing.”
With an “Mmmm,” Shelly slowly ran her soft tongue over my slit, as she’d done numerous times in the past, before pressing her tongue into me, causing me to push my head back into a pillow as that familiar ecstacy began to wash over me. Just as quickly, I felt Shelly move up my body, placing her wet mouth onto mine as we shared my juices she’d captured, our tongues passionately colliding and sliding against one another.
Raising herself up, Shelly looked down at me with her soft brown eyes and said, “It’s time baby. Are you ready? You certainly feel ready.”
With a smile I nodded to her as she used her right hand to line the cock up against my pussy. She slowly rubbed it from my hole to my clit, using my wetness as her lube. I closed my eyes as I enjoyed the feeling of it tantalizingly moving up and down over my most delicate parts.
Then, as I felt the rounded knob press against my opening I looked up at Shelly with moistening eyes and said, “I love you Shelly. Please, make love to me. Make me yours. I want to be yours, please.”
“Oh baby, you’re so beautiful,” she said. “I love you too baby, and love being the first to fuck you. I want you to enjoy this as much as I am going to.”
I was trembling with desire and anticipation as I felt the tip begin entering me, and I grasped Shelly’s arms for the dull assault and pain that was to come. But it didn’t. Shelly was extremely gentle, taking her time by pulling back and then slowly pressing in just a little deeper each time. The deepening fullness was something I’d obviously never felt before, and actually felt quite nice as I could feel my vaginal muscles pulse against the dildo’s firmness. With only a couple of the shaft’s six or so inches in me it seemed I could feel the sculptured veins caressing the sensitive areas inside me, and a pleasant electricity seemed to slowly engulf my body to the point that I really didn’t notice Shelly had buried the entire dildo’s length in me until I felt her warm breath on my face.
I reached up and pulled her mouth to mine, savoring her taste as well as the feel of our coupled bodies pressed together. The leather harness rubbed pleasantly against my most sensitive places as I rocked my hips in an attempt to have more of Shelly inside me. She slowly rose back onto her knees, keeping the cock buried as she first placed her hands on the backs of my thighs where my knees bend, holding my legs apart, and began pulling and pushing back and forth at an increasing pace and depth.
“Are you okay baby?” Shelly asked.
Between quick breaths I managed to reply, raggedly, “God yes. Don’t stop Shelly, please don’t stop. Feels so good. God, I’ve never felt anything like this!”
“Touch yourself baby, rub that sweet little clit of yours. This is going to feel so good to you. Yes, that’s it honey, do you like being fucked? Tell me what you need baby, tell me what you want.”
“I want you to fuck me Shelly, please keep fucking me. Feels so fucking good. Oh God I need you to keep fucking me!” I practically screamed as my juices were running, providing more than sufficient lubrication as my fingers rubbed my little bud up and down, and across, back and forth, occasionally grazing the cock moving in and out of me. I could hear the squishing sound the fake cock was making as it plunged in and out of my pussy, my sensitive opening clinging to the shaft’s pleasure-giving bumps and ridges.
“Oh God, I’m going to cum Shelly. Ugh, this feels so good, I’ve never felt anything like this. God Shelly I love you. I love what you’re doing to me. Fuck! Fuck! Oh, fuck!” I yelled as I frantically worked my clit as she ardently worked the cock in and out.
Oh baby you’re so beautiful. That’s it, let it go. Yes let it take you…,” she said, and were the last words I remember hearing her say as my body tightened as wave after warm wave rose from my stomach and seemed to wash over my chest, and down to my toes. I placed both palms on Shelly’s stomach, making her stop moving.
The next sensation I felt were my vaginal muscles pulsing and squeezing the firm shaft Shelly had buried in me. I reached up and grabbed at her, ending up with a handful of her hair, and pulled her to me, smothering her mouth with mine, and trying my best to drive my tongue down her throat and then exploring every crevice in her mouth, breathing heavily and noisily through my nose. Shelly pleasantly collapsed on me, and I bathed in her warmth as the tingles dissipated throughout my body.
“Monica. Monica, are you alright?” I recall hearing Shelly ask.
“Oh Shelly, thank you,” I breathlessly replied as I felt tears rolling down the side of my face. “I…I can’t describe to you how good that felt, how to explain it to you. But I do know it was different than any other time we were together. I….I,” I tried to continue, but couldn’t.
Shelly was kissing my face all over, and licking the traces of tears away from me. When we kissed I could taste the saline as her hands caressed my face.