I managed to graduate high school in 1966, still a virgin. It wasn’t the hardest thing I’ve ever done. At the time I was quite proud of myself. Not til sixteen did I even make out with guys and let them feel my tits—that usually got me excited enough to rub their dick and usually make them cum in their pants. They always wanted more, but that was a no-no. My pussy was off limits, except to me of course. Masturbation was good and bad. I loved to cum, but then it reminded me of the possibilities that awaited my deflowering when I got married one day. The waiting part was very frustrating.
I was blessed with what I thought was a very sexy body: c-cup firm boobs, a somewhat bubble butt, chestnut hair that I wore long, and a fun, adventuresome personality. I just knew that someday my husband would be thanking God for my attributes. This goodness ensured that I didn’t lack for dates, maybe not husband-quality ones, but nevertheless dates. The bad is that all this made it a strain to keep my virginity. A guy with two hands can somehow make them seem everywhere at the same time, creating a very passionate craving. When you really want to preserve your virginity this is not a good thing.
Since I did not have the means to go to college, my parents paid for my one-year course at the Grizwold Secretarial School. It looked like about the only opportunity within my means. I had some income from working nights at a local McDonalds, but not enough to live on my own, so it was staying home with Mom and Dad. That was not a plus in helping me find my future husband and lose my virginity.
The whole virginity thing was not really my desire. It had been beaten into my brain by my Mother and the Reverend at the church I’d attended faithfully every Sunday since I could remember. The mere thought of damnation and going to Hell petrified me. I was well aware of the possibilities my pussy held, but they had to be saved for my future husband.
I did date, mostly guys I either worked with or met at the McDonalds. None of them were what I considered husband material, but it was better than being stuck at home. After the appropriate number of dates, I’d always let them feel me up while I got them off in their pants. I’ll admit there were occasional guys that pulled their dicks out and got me to rub them ‘til they squirted their cum all over themselves. Each time, I turned away and secretly tasted the semen that stuck to my hand—it was neither good nor bad, it just was what it was, a somewhat salty, slightly sweet, moderately creamy/sticky substance that varied moderately from guy to guy. I developed a taste for it.
I graduated second in the class of 1967. That helped me get my job at Donnelly Screw & Machine. Little did I know how prophetic the company name was when I began work in the typing pool.
Looking at the general notice cork-board I saw a note from “Carol” who was looking for a roommate for her two-bedroom apartment. We hit it off and I moved in, somewhat to my parent’s dismay.
It didn’t take me long to realize that she and I were polar opposites, at least when it came to modesty and sex. The morning after my first night there, I was in my nightgown making coffee when she came out of her room stark naked and asked if it was ready yet.
“Ah, no, but it’s close,” I said, staring at her in some shock. It wasn’t just her nudity. Her pubic hair was quite minimal, at least compared to mine, and I thought, all girls.
“I see you’ve noticed my sparse pubes. Jim likes it that way so I keep them trimmed short. It’s actually more comfortable and Jim loves it, especially when he goes down on me. Oh my, he’s just so f-ing good at it!” she said with a dreamy look on her face. “You’ll meet him tonight. He’s coming over. I’m just gonna grab a quick shower, then we can gossip a bit before work.”
She spun and walked off before I could reply. The coffee stopped perking. I turned and poured myself a cup. Thinking about what had just happened, I found myself admiring her free and easy openness. The thought of a man being down there gave me goosebumps. At that moment I wasn’t sure if that was good or bad, however, I was very curious.
Jim did come over that night. He was one of the Regional Sales Managers for the company. We had some passing small talk, then they went into her bedroom. Her muted screams plus her squeaking bed springs communicated exactly what was going on. I began to doubt my virginity. Was “it” really that much better than my fingers? I knew one thing, I needed my own relief. So into my bedroom I went where my fingers brought me satisfaction but left me in doubt.
Some of the girls in the pool were assigned to specific men to do their typing and other secretarial work. Carol was assigned to Jim. At the beginning of my second week, I was assigned to Mr. Robert Blackmun. “Call me Bob,” he said when we first met. Two days later he told me that we needed to have a drink after work Friday night so we could get to know each other better. “And start dressing sexy. You have potential or you wouldn’t have been assigned to me. I can’t have you looking so dowdy.”
I knew I didn’t dress as showy as most of the girls in the pool but “dowdy?” That hurt. I talked to Carol that night about his comment.
“‘Dowdy’ is a little extreme. You have great assets. If you made them more obvious it would help your image and most likely, your career. Look at me and Jim, I stood out and now we’re going to get married.”
“Oh... I thought he was already married.”
“Well yeah, but he’s going to get divorced as soon as the time is right. He loves me, and his wife... well, he says she’s nothing but a pain in his ass and I make him happier than he’s ever been.”
“Wow, that’s great. I hope you’ll be real happy!” What did I know about these things anyway?
“Thanks! You know we’re the same size, so you can borrow any of my clothes until you can buy some new stuff, if you want.”
“Thanks! I don’t want to disappoint Bob or the company. He’s invited me for drinks Friday night. He thinks I have potential.”
“That’s super! You don’t want to disappoint him. These managers can make or break us in the company. If we make them happy and make them look good, it trickles down to us.”
The next morning Carol helped me pick one of her mini skirts, a scoop-necked top, and one of her pushup bras. The gold pendant I’d gotten for my high school graduation hung right in my newly created cleavage. I felt a bit embarrassed by seeming to be so provocative, but actually, I’d always been the odd one out; most of the girls dressed similarly.
When I walked to my desk that morning, I could feel the admiring gazes. Bob came over to me and said, “I see you took my advice. Love the new you, keep it up. We’re going to make a great team!” I felt a glow come over me and my pussy tingled. I’d have masturbated right on the spot if circumstances had allowed.
Later that morning Bob called me into his office to take dictation. “Ah, Abby, sit right here,” he said, gesturing to the chair right next to his desk.
“Yes... Bob,” I said, tentatively testing out his request to call him by his first name. He stood and walked around behind me.
“Good, Abby. I’m glad you remembered to call me by my first name. You seem a bit tense.” As he said “tense,” his hands rested on my shoulders and began to gently massage them. It was almost electric, the feeling he created. Nobody had ever had that effect on me before. His touch caused me to realize I really was tense. His magic fingers, as I thought of them later, triggered both relaxation, more pussy tingles, and nipple hardening.
“Ohh yes,” I quietly blurted out as I felt my face flush, along with my other feelings. In a wild mental babble, I thought: this is the man I want to fuck me, to take my virginity. Husband be damned, it’s time I got in on the fun.
His hands kept moving, fingers probing. Down my arms and back up. I knew my hard nips were showing. He couldn’t miss them. What must he think? I felt myself tremble slightly. Then he whispered in my ear, “You like that don’t you Abby?” I nodded my head. “Do you want me to continue?” Another nod. What was I doing? He’s my boss. Carol said not to disappoint him. I was terrified and thrilled.
Suddenly, he stopped and headed back to his desk saying, “That should do it. You seem relaxed now.” The fingers of his right hand grazed down my thigh as he walked past me. “You have great legs. Mini skirts are a blessing for both men and women. It looks terrific on you. Keep it up. So, onto the dictation.”
My head was reeling. My panties were soaked. My nipples felt like they would explode out of my bra. I was supposed to be able to concentrate after that?
I managed to get it together and get enough of what Bob said to type his memo. Then I thought more about what had happened. It finally dawned on me that my babble wasn’t babble, that everything I’d been convinced of from my youth was hokum. I was at least in the middle of the sexual revolution and it never touched me until this day. My whole outlook on life and sex changed. I knew enough to know I’d missed a lot—that had to change.
Friday arrived. The day for drinks after work. It couldn’t go fast enough. Not having a car or driver’s license, I relied on public transportation. Bob knew this and told me where his car was in the parking garage by our building. We left separately to avoid unnecessary gossip. I found his Oldsmobile Ninety Eight on the second level and slid in next to him, thinking: what a beautiful and expensive car, he must really be doing well.
Just for him, I’d dressed even sexier. Carol had several form-fitting, low-cut tops; I’d chosen one. My boobs were really quite defined. That, plus her shortest skirt, was a very bold step for me. Carol assured me that morning that I looked, “Good enough to eat but not slutty.” That thought lingered with me all day.
Crossing my legs after getting in the car left just enough skirt to cover my panties. He gazed at every inch of me without speaking, making me even more nervous. Finally, he spoke, “Abby, I don’t believe I’ve ever been this close to a woman as beautiful and sexy as you are right now. I’m very proud to be taking you out tonight. I just know that our relationship is going to be very productive for both of us.”
I was overwhelmed. I’d dated boys; he was a man. I felt so special. “Thank you for the compliment. I really enjoy working for you and hope I can continue to help you and the company.”
He smiled and said, “You’re really very special. Once we get to know each other better, our futures will be even brighter. You’re going places, Abby.” He reached across and brushed his hand down my thigh. My heart skipped a beat; my body shivered.
Never having been in such an enthralling situation before—oh sure I dated before, but they were boys saying stupid things and trying to feel my tits—I had no idea how to react, so I just gave him a big smile and told him how much I was looking forward to tonight. He exuded confidence; I was nervous as hell.
The club he took me to was nice. Booths, small tables, a dance floor, music from a jukebox. He grabbed a small, semicircular booth. A waitress in hot pants and a top tighter and smaller than mine came to take our drink order. Bob looked at me, I told him to order for me; all I knew was beer. A Moscow Mule for me and scotch on the rocks for him.
We spent several hours talking, drinking, dancing the slow ones. I loved when the Righteous Brothers songs came on. He held me tight each time we danced. His cock was always hard. I got more and more buzzed. His hand spent more and more time on my thigh, almost always moving, moving closer and closer to my soaking pussy. I was so wound up I wanted to take his hand and just ram it up against me, but, of course, I resisted that impulse.
Eventually, he asked me if I wanted to leave or do something else.
“Let’s go to my place. You have to get me back there sooner or later, and Carol is gone for the night, so we’ll have the place to ourselves.”
“Great idea! I was looking forward to seeing where you lived anyway. I’ll just get the check and we’ll be off.”
In a few minutes, we were back in his car, off to my apartment. This time I slid next to him. His arm casually draped around my shoulders—I snuggled in. He was much more assured, certainly more aggressive, than the boys I’d dated. His hand slipped down, cupping my boob as he rolled my nipple between thumb and forefinger. Moaning and snuggling closer, I unzipped his pants exclaiming, “God yes! Keep it up... squeeze them harder. You want me, don’t you?”
“You must know that.”
Stroking his cock, I said, “Say it!”
“Say what?”
“What you want to do to me.”
“Fuck you! I’ve wanted it since I first saw you. I want to fuck you ‘til you beg for mercy!”
“...’til you beg for mercy.” That reverberated around in my brain. God, was that possible? Mercy from what? It was both scary and exciting. It convinced me that he had to know my condition, so to speak.
“You should know I’m a virgin.” Even though I was convinced that my fingers and hairbrush handle had long since removed any physical barriers, it would technically be my first time. I just wanted to hear his reaction—it was silence.
Then, “What!? No. You can’t be. Well, I know you could be. Anything’s possible, I suppose... but you’re an experienced woman. You’re just fuckin’ with me... right?”
He called me a woman. I’d wanted some reaction, but I didn’t know exactly what. That was it! I was no longer a girl. In his eyes, I was a woman... I was a woman and wanted what a woman desired! In that moment, for that night, it was cock and satisfaction. Deep, long-lasting satisfaction!
I chuckled. “Yeah, I’m fuckin’ with ya. So you better take good care of me.”
“You also better take good care of me,” he said as he released my boob and began to push my head down. “Suck my cock until we get back to your place. I want to feel how a ‘virgin’ gives head.”
Carol and I had discussed this in some detail. I’d been close, but never actually had a cock in my mouth, let alone had one cum in my mouth, but I’d tasted cum and, for the most part, enjoyed it. I guess Bob approved because all I heard for the rest of the drive was, “That’s it, baby, suck my dick. Lick it, kiss it, suck it. Damn, you’re good at this, Abby.” He started laughing as he went on, “A virgin. That’s a good one honey. I’ll admit you had me there for a minute. Oh damn! Fuck yes baby. I love the way you suck my cock!”
Once in my apartment, there were a few moments of what I thought of as hesitant urgency coupled with ordinary awkwardness. We both wanted the same thing, but I didn’t want to seem outrageously slutty, or even clumsy, and I think he was trying to be very respectful; ultimately, we embraced and kissed. In the midst of that, he undid my bra and began to pull my top off. Stepping back, I gave him room. Up and off they went. “They’re beautiful,” he said.
I did a pirouette, and said, ”Thanks” while thinking: he’d better mean that!
He exhaled like he'd been holding his breath for minutes, saying, “Oh god yes! You’re so fucking hot. Let’s do it.”
I led the way, thinking: less than a month ago I was a self-conscious, unsophisticated, somewhat naïve girl; now I was a woman leading a debonair, experienced, successful man to my bed. I ran the last few steps and threw myself on my back, spreading my legs somewhat as I hit the bed. Resolve was my watchword—resolve to exhibit the qualities of a sexually experienced woman.
Carol had described the joys of receiving oral sex. I wanted it! Bob understood my spreading legs and took the hint. Soon, he had me squirming and moaning. This was so much better than my fingers! I entwined my hands in his hair and pulled him tight to me—the resulting orgasm engulfed me, radiating from my pussy to my fingers and toes. “FUCK!” I shouted as my whole body quivered.
Smiling, he began moving up, his hard cock bouncing in anticipation. “I guess I found the right spot,” he said in a proud voice.
“I guess you did,” I gasped out. By then he was rubbing his juice-covered face on mine and was about to kiss me.
“I thought I’d share your juice,” he said. “It tastes so good. I love your copious flow.”
“Too much?” I asked. What did I know? I’d never been this aroused. By this time I could feel his cock head rubbing against me; I really wanted it but...
“No! God no. I love that you produce so much. It’s sexy as hell.”
“Before you push in, rub it up and down my pussy. Tease me a bit and then go in real slow.” Not knowing what to expect, I didn’t want any surprises, plus I didn’t want any virginal thoughts entering his mind.
“So that’s the way you like it. Cool. I like a woman that’s not afraid to speak up about her desires. Slow and easy it is... until it isn’t,” he said with a chuckle.
At that point, I could only imagine. Not too much later I found out.
He did tease me a bit. It felt good to feel him sliding up and down between my lips. Soon, I felt his first push. Just its head entered me and pulled back. Then in again, a bit further. I was feeling the stretch. He was bigger than the few guys I’d actually seen, so I didn’t know what was really normal. He continued that slow in and out, each time going deeper. It was starting to feel really good. I let out a moan of pleasure.
“You like that huh? Your pussy’s really tight. It feels terrific! You like my dick?”
“Oh yeah! It’s great. I feel so full and I’m tingling all over. I love it!” Right about then he was fully in and began to speed up. I thought: this is great and quickly becoming beyond anything I’d imagined or inflicted on myself. “Oh god! Fuck me! Yes. God yes! Faster! I’m... I’m... going to cum. Shit yes now! Fuck!” I started squirming and slapping the bed. “Oh my god, oh my god, oh my god. I never—” Imagined was going to be the last word but I stifled myself and just gave in to the feelings.
He continued, sometimes slow, sometimes fast, making me cum over and over. Then, buried deep in me, he paused and groaned as he held me tight. I felt his warmth fill me. “Oh fuck, Abby, it’s so good. You’re so good. Damn, woman, you know how to make a man happy.” He chuckled and went on, “And I thought you were probably an innocent, inexperienced girl. You’re a fooler, baby, and a sweetheart.”
I laughed, thinking it was a good thing I’d gone to that clinic and gotten the pill. It was a just-in-case kind of thing and this was that case. Being the petite girl that I am, I said, “Fun comes in small packages.” Then, impulsively, “You’re not done for the night are you?”
“Me? Hell no! Don’t worry about my stamina. A little breather and more of your sweet mouth, we’ll be back at it.”
I’d succeeded! He never suspected. I lost my virginity and had an amazing time doing it. He managed two more times that night. My enjoyment increased with each session. Just before falling asleep, I remember thinking how I wished I’d taken this step years before.
When my eyes fluttered open the next morning, Bob was on his back, lightly snoring, his cock holding the sheet up like a tent pole. (Later Carol explained all about “morning wood.”) It was so inviting that at first, I began playing with myself and then carefully moved so that I was under the sheet, between his legs. Ever so gently, I eased him into my mouth, delighting in feeling it slide in and out. Just a few hours ago he’d brought me so much new-found pleasure, I wanted him to awaken feeling what he’d told me I was so good at. Not to mention that I loved doing it.
Soon, I felt his legs move. Then the sheet came flying off. I looked up at him. Our eyes locked; he moaned; his head flopped back on the pillow.
“Oh god, Abby. What a way to wake up. Did I mention how good you make me feel? How good you suck cock? Oh, Baby, keep that up and I’m going to fill your mouth.”
Keeping it up, I managed to get out an “Mm-hmm” as I slid up and down his shaft. I tasted a bit of liquid from him, then his legs tightened.
He held my head as he began spurting. “Oh, Abby, swallow it all! You’re so fuckin’ good! Yes Baby, yes.” I swallowed and swallowed, loving his taste and somewhat amazed at the whole thing. When he finished I swirled my tongue around its head to lick the last drops. He jerked and then laughed as he let me go. “It’s super sensitive. You really did a number on me. Come up here,” he said as he pulled me into a passionate kiss.
When he departed that morning, he left me with the thought that I would soon be his personal secretary, with a raise in pay and be traveling with him on business trips. I was thrilled.
The following Tuesday, Miss Burns, my supervisor and the rigid boss of the whole typing pool, tersely informed me that I was to immediately report to Mr. Blackmun. I was to be his private secretary, replacing Mrs. Wilson, who was being reassigned to the typing pool temporarily. Flipping her hand and turning away, she said, “Get your things and go.” That was that.
Bob and I maintained a very professional, boss-subordinate relationship at the office while fucking like bunnies two or three evenings a week plus every weekend. At work I was Miss Nightingale, other times and other situations, I was his baby, lover, girl, honey, sweetie, woman, and my favorite, patootie. My sexual enjoyment grew and grew. Everything he suggested, I tried, and mostly enjoyed. Some of the things we did made me think I was becoming, or maybe already was, a slut. I mean I actually learned to enjoy him fucking me in the ass after only a couple times. Did good girls really do that? I was embarrassed to ask Carol. I trusted that Bob loved me and believed him when he told me that I’d just been extremely sheltered from sexual pleasures.
It was only on Monday, four weeks later, that he told me we were going to St. Louis the following week to meet with a very important potential new client. He was counting on me to help him get the contract signed—I was thrilled. I’d never been away from Chicago. A train trip to Saint Louis. Staying at the Mayfair Hotel, which was known for its luxury. I knew God had overlooked my sinning and was shining on me.
I promised him that I would do whatever he needed to help him close the deal. I wasn’t really sure what that could be, since he was the experienced salesman and I was just his secretary. But then, I was his personal secretary who handled all of his administrative and organizational needs. I knew all the financial figures related to our proposal. I guessed that’s where I’d be most useful.
The week before he’d told me about the trip he’d given me a Frederick’s of Hollywood catalog, with some suggested items circled, telling me to order anything I wanted. “I want you to look and feel sexier than you ever felt before. Order things for day, evening, and nighttime. You’re going to be important in closing accounts. You’ll need to look very alluring.” It was serendipity that he’d given me the catalog and now we were going to secure a new account.
I’d never before seen anything like their apparel. In one way or another, it all screamed sex! Which was not bad, but it was such revealing clothing, if you could even call it clothing. Much of it left little to nothing for the imagination. I showed it to Carol to get her opinion.
“Wow! Those are some hot, sexy threads. You’ll never see that stuff in Sears,” she said laughing. “Jim has been wanting me to get a Frederick’s catalog, now I see why. So what are you going to get? Bob must really want you to look sexy with a capital S!”
“I can’t decide. He’s marked some things he likes. They’re very risque. I want to please him however I can, but I don’t want to look like a walking advertisement for sex. I really do love some of the lingerie. It’s super sexy.”
We poured over it. Making lists. Adding, crossing out things. Finally coming up with an order that covered every style and occasion that Bob wanted. He’d seemed very anxious for me to order, so I mailed it special delivery the next day with rush shipping requested. Carol and I were anxious to try it all on since we were both the same size.
Within a few days, there was a package for me by the mailboxes of our apartment building. The return address just said Frederick’s, Hollywood, Calif. My heart skipped a beat as a shiver ran through me when I picked it up.
Carol was already home so we tore into the box. One by one, I pulled the various accouterments from the box. We ooh’d and aah’d, giggled and laughed, over everything as we made comments on their provocativeness, trying them on while imagining and fantasizing about the various situations we might find ourselves in while wearing them.
While doing this, we were both either nude or close to it. Our cavorting around and expressing our sexual fantasies left us both in an ardently impassioned state as we removed the last of the lingerie. We stood close to each other, naked, not seeming to know what to do next. Our eyes locked. We both stammered out a few rambling, muddled words. Carol reached out, slowly brushing her fingers across one of my nips. I gasped. My eyes closed. My repressed desires surged.
My body was screaming: YES, MORE, RESPOND—my mind was whispering: no, stop, it’s wicked and naughty. I blindly reached forward, finding her breasts. Seemingly out of my body, I let my hands hold them as my fingers caressed. I heard her gasp.
“We shouldn’t do this,” I murmured. “It’s so sinful and naughty.”
“I know,” she said, pulling me close, “but it feels so right... doesn’t it?”
“Oh my god, yes!” I replied as one of her fingers slipped into me.
“Squeeze my tits hard as I finger you,” she said just before our lips met. Spreading my legs as best I could, she slammed in and out of me as I tweaked and rolled her nips.
Soon she turned me sideways and began rubbing her pussy against my hip as she kept fingering me. I could barely stand as she pressed hard against me and her finger continued to work its magic.
“You love this don’t you?” she whispered in my ear.
“Yes,” I gasped, “you know I do. You’re going to make me cum!”
“I know I am, and then we’re going to my bedroom and you’re going to eat my pussy until I get off. Don’t think I haven’t noticed you looking at my shaved beaver. I might shave yours. Would you like that? I’ll bet Bob would. You know the girls at all the local strip clubs go bare. It’s the coming thing.”
“Oh god. I’m so bad. You’re right, I’d love it. I’m just fearful of becoming a slut. Fuck! I’m so close; keep it up!”
“We’re both sluts already sweetie. You just haven’t fully embraced your sexuality yet. Hell, men embrace theirs halfway through high school, while you and I worried about keeping our legs crossed and their hands off our boobs.”
“FUCK YES! Now,” I shouted as my legs began to weaken. Carol held me up. “Goddamn, that felt good!” I said a few seconds later, giggling as the feeling began to pass.
The fun continued in her bedroom. I experienced several more firsts by giving and receiving oral plus rubbing our pussies together for joint orgasms. Admitting that she was right about us being sluts, I vowed no more holding back for me anymore. My newly shaved vag was a delight.
Bob asked me to dinner and a movie for Saturday night and to plan on spending the night at his place. He usually wanted to stay at my place so I was extra pleased. I wore a new, very short, form-fitting black dress with a deeply scooped neckline and one of my new pushup bras to show my assets, loving what I saw as the new, grownup, modern woman emerging from her virgin chrysalis.
He’d reserved a semi-circular booth so we could sit close together. As soon as he’d ordered our pre-dinner cocktails he began to run his fingers up and down my thigh. I snuggled closer and told him how naughty he was being.
“You’re my girl. That gives me certain rights of access. Besides, no one can see; the tablecloth hides everything.”
“Am I really your girl, to the exclusion of all others?” I so wanted to hear him tell me that. If he said yes I was going to tell him to feel higher. It was going to be a secret until later at his place, but I was dying for him to know about my hairless state, especially if I was his exclusive girl.
“Of course you are! I thought you knew that. We’re partners, friends, and lovers.”
“In that case... I’m wearing a pair of the new Frederick’s sheer panties. You might want to caress me a bit higher...”
“You are so damn sexy!” he said, as his hand glided up my thigh and caressed my pussy where he eventually discover my lack of hair. “Abby!” he blurted out. “You—”
“Shush!” I quickly responded.
He whispered back, “You’re so smooth! Oh my god, I love it. You knew I really wanted this, didn’t you? I didn’t mention it cuz I didn’t want you to feel forced. Let’s skip the movie.”
“As tempting as that is, we’re still going to the movie tonight Mr. Blackmun. I really want to see The Godfather. Then I really want you, in all ways.” He moaned in semi-mock complaint. “Remember you’ll have me as much as you desire until Sunday night,” I added.
Perking up, he said, “And Baby, you know my desire will be endless.”
“If only,” I said, teasing him. When he gave me a pouty look I added, “You know I’m always extremely satisfied... lover boy!” That brought a smile to his face.
He made good on his endless desire. The first thing he wanted to do when we got to his place was to go down on me. I’d certainly made the right choice in letting Carol shave me. He was over the moon about it, licking and kissing me from my tush to my belly button, with most of his attention centered on my pussy, making me cum twice. When we were doing it doggy style he spanked me devilishly as he fucked both my pussy and ass. Between the sting of the slaps and the thrill of him banging me I thought I might pass out from orgasm overload, if there is such a thing.
During the few days between that first experience with Carol and the weekend with Bob, I discarded all my inhibitions and hang-ups about sex and embraced my slutdom, resolved to be a “modern woman” as Carol had referred to what had become our sentiments regarding sex. Little did I know, at that moment, how that resolve would be tested.
We called that our lost weekend, substituting sex for alcohol, mostly. He got me home Sunday afternoon so I could rest and get ready for our trip on Monday. He was going to pick me up in the morning to catch the 7 am train that would get us to Saint Louis by 4 pm. We had an 8 pm appointment with Mr. Wilkinson at the hotel for drinks and dinner as sort of a get-acquainted time before the serious business discussions the next day. At least that’s what he told me.
At first, the train was exciting, since I’d never been anywhere, but it eventually became somewhat monotonous—we both slept part of the way. The hotel was magnificent. Bob had booked a suite for us. It was nicer than any home I’d ever been in.
When we checked in Bob inquired about Mr. Wilkinson and was told he had the room connecting to our suite. I thought this odd and gave Bob a quizzical look. He said, “I’ll explain after we get settled.” With that, we were shown to our suite.
Once there, Bob ordered martinis. I freshened up and unpacked a few things. The drinks arrived and we sat by the window to enjoy the view of the city.
“So why does Mr. Wilkinson have a room here? Are we going to have the business meeting here? Aren’t we meeting him for dinner tonight?”
Bob hadn’t really shared many details of how the discussions would take place and I’m a naturally curious person.
“I’ve been meaning to talk to you about that, but there never seemed to be the right time. Here’s the thing... ah, let’s have more of our martinis.”
We had another sip or two. Then I said, “Hello. Is this my Bob? The guy who’s never at a loss for words.”
After a weak chuckle he said, “Yes, it’s me. Look, here’s the thing. I’ve been working Wilkinson for months just to get this meeting. His business would mean a large increase in the company’s bottom line. Plus a significant bonus for me, which I’d split with you, if we pull this off.” Pausing for another sip.
“Why do I feel like you’re talking around something? I already know all that, except for the bonus split, which is very nice by the way. I could sure use the money. Tell me what seems to be worrying you.”
“Okay, here’s the thing—”
“You’ve said that three times now. Now just tell me ‘the thing’.”
“Okay. Wilkinson has all but directly told me that I need to have a hot girl for him to spend the night with before he’ll sign any deal. He’s got some strange idea that’ll show trust between us.”
My heart started pounding as I tried to stay outwardly calm. “And at dinner tonight I’m to be that ‘hot girl’?”
“Well... ah, yes,” he admitted, seeming quite uncomfortable.
“Hence the hot new clothes?”
“Partly. It’s also for my benefit. You radiate sexuality and the clothes double it,” he said with a hint of a grin.
I went quiet. My mind was going a thousand miles per hour. Of course, I was totally shocked, but what did I really know about the world, the business world in particular? I knew women were not treated equally to men. I learned that through my year at the Grizwold school. Then there was Carol. She really gave me an education about relationships and expectations in the business world. Many of the girls that worked at Donnelly’s dated guys that worked there. Dating married men was not uncommon. She was living proof of that. She’d hinted at other things that went on but wouldn’t get real specific when I pressed her, so I let it go. How could it affect me anyway was my thinking.
I was almost twenty and so naïve—I thought I was a slut, HA!.
My new entry into slutdom, as I thought of my newly found sexuality, was really just barely an entry. This opened my eyes further. Part of me thought it really was hot that Bob wanted me to do this. After all, it wasn’t love or a relationship, it was just sex, and who knows, it might really be fun. Plus I wasn’t kidding about needing the bonus money. But did that make me a prostitute? This was obviously a much more complicated world than I’d ever imagined.
Bob was fidgeting because I wasn’t responding. Good, I thought, that’s the very least he should go through for springing this on me. After more thoughts along the Bob and me line, I was ready to talk.
“So, what about you and me? Am I really your girlfriend? Are you going to pimp me out regularly?” I’d learned that word from Carol.
“Yes, you’re my girlfriend. No, I don’t want to pimp you out, ever. This might not even happen. He’s married and just wants something different. Apparently, his wife is ‘plain vanilla’, to quote him. I’m sorry I couldn’t get up the nerve to talk to you about this before now. I’ve never done something like this before, but it does happen.”
“It happens generally or at Donnelly specifically?”
“It happens at Donnelly... and other places I’m sure,” he said, looking uncomfortable.
“Okay, give me an example.”
“Please don’t press me for specifics. It’d just be gossip anyway. Ask Carol about it.”
“Carol’s done it!?”
“I didn’t say that. I know she knows about it. That’s all I’m sayin’.”
I went quiet again, making him nervous.
After more thought, I made up my mind. “Okay, I’ll do it. Your girlfriend is going to fuck this Wilkinson guy. I’ll suck his cock and maybe even let him fuck my ass. I’ll even tell you all about it later. Heck, you’ll probably hear me scream when he makes me cum since I’ll be in the room next door. That should be thrilling for you!”
“Oh god. What have I done?” His face was white as a sheet.
As I finished my martini, I said, “Well, that’s on you. It’s your plan. I’m going to wear my sexiest outfit and you’re going to take me to dinner with him and show me off. I want to be the hottest woman there. I want Mr. Wilkinson to crave me from the moment he sees me.” That’s exactly how things went.
The three of us met at the Maître d's stand and introduced each other. The formalities were quickly dropped; we became Eric, Bob, and Abby. Eric looked at me with the stare of a wolf on the hunt. I was mesmerized. He had Paul Newman eyes, piercing blue. My nipples reacted with hardness as I felt the heat begin between my legs.
We were seated in a curved booth—me between the two men. Having crossed my legs, my skirt rose to just below my panties. My half-cup bra pushed my boobs up and together so they looked almost twice their size. The gold pendant hanging in my cleavage focused Eric’s eyes right where I wanted them.
Bob tried his best to discuss business as Eric just wanted to enjoy the evening and talk to me. By the time we were ready to order dessert Eric’s right hand, which had been slowly and gently caressing my thigh, found a seemingly permanent home quite high up. I suppose that was somewhat emboldened by me earlier uncrossing and slightly spreading my legs. Now, I was fantasizing about when he would discover my significant saturation. It was a combination of the number of drinks I’d had and my actual interest in Eric, who I found both interesting and handsome, to put it mildly.
Just as the waiter was leaving from serving dessert, Eric’s pinky made substantial contact. I closed my legs, lightly trapping his hand. Our eyes met. His finger wiggled as his right eyebrow rose, creating the classic questioning look.
“Mmm,” I purred. “Interested?”
“Definitely.”
“What a coincidence.”
He leaned over and whispered, “I have a room here.”
I whispered back, “I have all night, but then Bob and I are meeting an agreeable gentleman in the morning to sign a contract with our company. Does that work for you?”
“I anticipate no problems.”
“Wonderful. I’m looking forward to the rest of the evening.”
Spreading my legs slightly released his hand. Bob had stayed silent during this “moment” Eric and I were having. I’m sure he had a sense of what was transpiring between us. After all, he’d set it all in motion, and, after my initial stunning shock, I’d agreed to it. Now I was actually quite looking forward to it. Eric was about to become only my second intimate partner. He thought I was twenty-five and probably a most experienced woman. I knew I wouldn’t disappoint—Bob and Carol, in their own ways, had primed me very well.
Soon, dessert was finished. Eric stood, thanked Bob for dinner, and told him he looked forward to tomorrow’s meeting to finalize the contract. Then, offering me his hand, he said, “Abby and I are going to spend some quality time together. Thanks for introducing us.”
Taking his hand, I slid out of the booth, looked back at Bob, saying, “See ya later” and walked off with Eric’s arm around me. I put my free hand behind me and waggled my fingers at Bob, then I gave him the finger.
Eric spent the time walking back to the room telling me how sexy I was, how much he was looking forward to spending time with me (his polite way of saying fucking me), that he hoped I wasn’t feeling obligated or somehow coerced into doing this (him trying to tell me he didn’t think I was a total slut) and that he felt like such a lucky guy to be able to spend time (there’s that phrase again) with a woman as intelligent and perspicacious as me (I’m still not totally clear on perspicacious but I can spell it, so I guess I do have some intelligence).
Once in the room, we embraced and kissed lustfully. Then my dress’s zipper was brought down to its stop, just above my ass crack. The small talk was over, at least for the moment. When we eventually parted, he stepped back, taking the shoulders of my dress with him. Letting it go allowed it to puddle at my feet.
I stepped out of it, walked a few feet away, and did several pirouettes. Those ballet lessons weren’t lost on me.
“Perfect, absolutely perfect. Your tits are about to boil over the top of your bra. I’m dying to see all of you.”
I walked back to him and gently shook them back and forth, almost brushing his chest, as I said, “Well, you know you can see whenever you want, but they say that a slow surprise makes the ending even better... and we have all night. Your choice.”
“Oh god! You’re killing me. You know it don’t you? Do you always tease guys like this? You’d strip naked in a second if I asked you wouldn’t you?”
I tried out a kind of sexy, pouty look and said, “Of course, baby. Whatever you want tonight... Daddy.”
“Oh fuck! Turn around. I want to feel them before I see them.”
A half turn and I backed up tight to him, rubbing my ass against his obviously hard cock. He made short work of my bra’s hook. His hands were cupping my boobs before my bra hit the floor.
“What can I say but perfect. They’re soft but firm. You really don’t need a bra do you?”
“Only to stop the jiggle and hide my nips, the ones you’re squeezing now. Oh yes, Daddy! I love that. Just like that. You have a magic touch. You’ve got me soaking, but you already know that. I can feel how hard you are.” This made me think of Carol and what I called my conversion therapy—my pre and post-virginity guidance. Our talks gave me a head start on men and sex. This isn’t to disparage men, I love them. She just taught me much about handling sexual relationships for fun and profit, as the saying goes.
While I was thinking of Carol I reached back and started stroking his cock.
“Oh, Abby. You’re the one with the magic touch. You really know a thing or two about pleasing a guy. Will you suck me? Later I mean, not right now.”
“Of course, I will. Can I tell you a secret?”
“Of course. Anything.”
“I really love to suck cock. I love how it feels sliding in and out of my mouth. It’s oral fucking. It always gives a guy so much pleasure. Plus when they cum, and I swallow it all down, it’s like I’m keeping a special part of them—all their little swimmers. Is that just being silly?” I was doing my best to play the role that he’d more or less laid out for me while we walked to the room. Plus, I actually do love giving blowjobs.
He started to laugh. “I’m not laughing at you. You’re a treasure. I wish... well, that’s all water over the dam.”
“Go ahead. Tell me what you were thinking. I keep secrets very well.”
“My wife... she’s not into oral... at least not the giving part.”
“Wow. Sorry. At least for this night you can have all you want. In fact—” I paused as I turned back to him and dropped to my knees. I had his pants and boxers down in seconds. “No time like the present,” I said as I engulfed his manhood.
“Oh fuck!” he uttered as I noticed him go a bit weak in the knees and put a hand on my head for balance. “Yes... yes, yes, yes! Suck it. Oh my god. It’s been so... Oh Abby, you really are a treasure. I’ll cum soon if you don’t stop.”
“Your call. I’d love to add your little swimmers to my collection.”
He never said another word. He just held my head as I moved back and forth. Soon I tasted his precum, which was quickly followed by spurt after spurt of the main event. He groaned through this and when he was completely drained said, “That was unbelievable. You even took all of me sometimes.”
“Practice makes perfect,” I said with a giggle. Carol had taught me with a very flexible dildo.
“Well, no worries, one thing I do have is stamina and repeatability so the fun will continue.”
Then we both got naked and hit the bed. He was somewhat speechless when he noticed my hair-free pussy.
“Abby... you’ve no hair down there... on your pussy. Is there... I mean... I’m sorry. I must sound stupid. It’s just that I never expected... that. Actually, it’s beautiful, wonderful.”
“I find it liberating and sexy. It’s a very new trend that I’m trying out. You approve?”
“Good god yes! Let me take it for a trial run, so to speak.”
With that, I stretched out, legs spread. He quickly found his position, starting to kiss and lick me, from my ass to my clit, without another word. That brought me several orgasms, all of which he seemed to enjoy almost as much as me. As I gasped for breath, he paused, saying, “This is wonderful! You’re so smooth. I can see and taste you so much better with no hair to get in the way. I highly approve.”
At that point, burning with desire for a good fucking, I held out my arms.
“So is thoroughly modern Abby ready for a deep, fierce fucking? She seemed to thoroughly enjoy the trial run.”
“The deeper and fiercer the better,” I said, hoping I wouldn’t regret that.
As he advanced into position, he collected my legs under his arms and sort of gathered me to him, effectively preventing any movement on my part. Then, with minimal probing, his cock found its target. He pushed in as we began to kiss. A few short strokes to pick up my juice and he was off to the races!
“Good god your pussy is tight.”
“I know.” I giggled as I squeezed his cock. “I can make it even tighter.”
“Ahh,” he uttered with a smile, “always a surprise with you. If I was your age I’d never let you go.”
He proved his stamina by almost exhausting mine. Orgasm followed orgasm. He took me on a roller coaster ride through the Palisades Park of orgasm land. While normally not quiet during sex, this evening I was extra loud to make sure Bob could hear me through the wall. I wanted him to know exactly how much Eric was thrilling me.
He had been changing up his tempo, I was sure to avoid his orgasm, but finally, he could no longer restrain the urge.
“Oh, baby, I’m going to cum soon. It’s building, building—I can’t resist any longer.”
I shouted, “Give it to me, lover! Shoot your hot spunk in me. Fill me full!” He groaned as I felt his cock begin pulsing and his warm spunk flowing into me. “Oh yes, baby! I feel it. Give me every drop!” I really meant that but I also wanted Bob to hear my passion.
He relaxed with his last pulse and asked if I could take it if he just stayed in me for a few minutes. Somehow I wasn’t feeling his weight and loved the feeling of our connection so I said, “Of course. I love you in me. If you were my age I’d make sure you never let me go.”
He was much stronger than Bob and the sex was much more aggressive, more wild and unrestrained. Carol had talked to me about “rough” sex. I thought this was exactly what she’d meant—I loved it!
We eventually untangled and separated ourselves. I was going to take a shower. He asked me to forgo it because he loved my smell and loved “...seeing me drip out of you.”
I smiled, telling him, “I’ll happily dispense with it, just for you.”
We moved to the windows, standing naked, me dripping, as we drank water and gazed at the new shiny steel arch over the river. While we were there he remarked on what a cute, sexy ass I had and asked me if I’d ever tried anal sex. I figured this was his indirect way of asking if he could ass fuck me. I replied, “Yes” and left it at that.
He patted my butt as he followed up with, “Soo... what did you think?”
Knowing what he meant, but not wanting to make this easy, I said, “The view is amazing. How did they ever build that arch? Can you go in it?”
“Ahh... yes. They say there’s sort of a reclining train that goes to the top, but I was referring to my comment about anal... sex I mean.”
“Oh... I see, well yeah, it was... interesting.”
Smiling, he replied, “Well, that was an ‘interesting’ answer. Pretty noncommittal. Are you just ambivalent about it?”
“Oh no, I’m not at all ambivalent about it.”
“Now you’re just teasing me aren’t you?” he asked as he slapped my ass a bit harder.
“Ow!” I said with a grin and wiggled my butt. “Okay, I guess I was somewhat teasin’ you. I kinda enjoy it as long as it at least starts out gentle and slow, to get me used to it.”
“Now that’s a darn right useful piece of information,” he said as he slapped my ass again. “Did I mention how perfect your tush is?”
“Yup,” I said as I thought: I’m definitely gettin’ ass fucked tonight. Well good, as long as he was payin’ attention to my gentle and slow comment.
“I think you’d look perfect in bed, on your knees, face in the pillow. Whaddya say?”
I was ready to get back on that roller coaster. “Take me back to Palisades Park, Daddy.”
He started laughing and said, “Well, I’ve never been there, but I’d love to take you.”
I started laughing also. “You already took me there once.” He looked confused as I got on the bed so I just said, “I’ll explain later” and assumed the requested position, wiggling my elevated butt as an invitation.
Wasting no time, he once again slathered his cock with my juice and pushed in my vag as he continued to slap my ass. He was definitely more physical than Bob—I was getting into it. Pushing back, we were tight against each other.
“Oh god yes. That’s so good. Fuck me and beat my ass!” I’m sure I didn’t have to say that cuz he was already into a rhythm of long, deep strokes. Those, combined with the spanking I was receiving, soon took me to orgasm park. As I clawed at the pillow I shouted, “Oh fuck Daddy, I’m cumming already! Yes, yes, do it. Spank my ass! Oh god!”
Lost in my lust, I felt a finger go into my ass, making me blurt out, “Yes Daddy. That’s it, finger me. I love it!” Some part of me mentally countered with: don’t encourage him. I ignored it. I was having the best time of my life, to that point anyway, and I wasn’t going to permit negative thoughts.
“Like that do you baby? You know I’m going to fuck it soon don’t you? My cock is going to stretch you out and plumb your depths, make you scream. Tell me how much you want it, baby.”
As I was about to gasp out an answer a second finger went in. I laughed to myself thinking: double the fun. Then, instead of answering him, I said, “That’s it, stretch me for you. Tell me how much you want my ass Daddy. Tell me!”
“I love your ass, baby girl. I want my cock buried deep in there. I want to hear your screams of delight as I make you cum. Now tell me how much you want me.”
“I want you to take my ass and make me cum and cum. Do me slow and then ravage me. Spank me and own my ass. Fill me with your spunk!”
Time had lost all meaning for me. I’d been riding that roller coaster through countless peaks and valleys. I felt like it could go on forever. Part of me knew that he’d been scooping my juice and using his fingers to push it into me and smear it on me. That part knew it was happening soon. The rest of me was busy still riding that coaster.
Then, with no warning, he pulled out his cock and fingers. That startled me back to a semblance of reality.
“What the fuck!?”
“Time to plunge that ass baby! Reach back and spread your cheeks.” Being super excited and slightly apprehensive I sighed and did as requested. “That’s my girl! Wow, you got a small gape already from my fingers. You’re definitely not a newbie to this, are you? We’re gonna have some fun now!” That’s when I felt the first pressure. He was slow and steady, just perfect. I was breathing deep when he popped in. “Yes! You opened like a pro.” He quickly followed with, “That’s a good thing. I didn’t mean to imply anything... skanky or anything like that.”
“No offense taken. I’m liking it so far. Daddy’s got a nice cock. You’re so much bigger than my other lovers. Mmmm.” Here I was taking only the second guy I’d ever even contemplated letting into my ass and I was ‘a pro’. I knew it was a dirty, nasty thing to do but I loved it and felt like hinting at experience I didn’t have. Carol had told to me to “do what you love.” I was.
“Oh, baby! And I thought your pussy was tight, your ass is amazing. Okay, here we go. Let’s take this baby for a test drive. You’re a real sports model.”
I dropped my hands. He immediately spanked me twice as he started fucking me. He was slowly rubbing more of my juice on his cock and me as he pushed deeper and deeper. Such a different feeling, but exquisitely sensual.
Once fully in, he began speeding up. His balls began slapping against my vag, right down to my clit. It was a different roller coaster but that special feeling was starting.
“Mmmm, oh yes Daddy yes. Ahhh, so good, so deep. Fuck me, pound me, don’t hold back. OHH, fuck yes Daddy! Like that, do me, fuck my ass!” That roller coaster had peaked the hill and was heading down for the second one.
He went on and on. I thought I’d either go insane or pass out if he kept it up, but neither happened, just more orgasms and spanks. I literally screamed several times. Part of that was for Bob’s benefit and part was just a natural response to the coaster ride Eric was giving me.
Finally, he shouted, “Fuck baby! I’m gonna cum, gonna fill you. Oh, oh, oh... yes... right NOW!”
He buried himself fully, grabbing my hips with a bear trap-like grip. I could feel his rhythmic throbs as he emptied into me. Exhausted, I crumpled to the bed. He followed me down, still fully embedded in me, his weight fully on me—it was his turn to gasp for breath.
The bed was quite soft so we both sunk in; his weight didn’t bother me, it was almost like we were floating. He’d outdone himself and deserved a bit of rest—besides, I loved his cock in me.
For some reason, the new song, That’s the Way Boys Are by Leslie Gore, popped into my head. I started humming it and squeezing his cock in time as the lyrics ran through my mind. There was truth in them. We each had our lot in life, men and women. I had a much better understanding of mine—I was proud and happy to be a woman.
Eventually, we separated, both of us drained, literally and figuratively, from our uninhibited, wanton evening. We managed showers, then fell into bed, sleeping until the alarm woke us with just enough time for the meeting.
Wearing a hotel robe, I went through the adjoining door to the suite. When Bob saw me he couldn’t apologize enough about his behavior, his getting me into this. Eventually, I told him enough was enough—I’d taken one for the team and it was behind us. I left out the part about how much fun I’d had with Eric and what a great lover he was. He never mentioned my screams of delight. We were sort of even. The contract was signed and I was a “modern woman.”
