Tuesday morning I took special care in getting ready for work; knowing it was Jacks usual day to frequent the library. I’d spent the night (like most others that week) dreaming of Jack’s sweet seduction and our “date” last week. Scanning the conservative work clothes in my closet I finally settled on the form-fitting black skirt and the soft red sweater. I was so nervous; it took me several tries just to get the seams straight on the backs of my stockings. The morning seemed to take forever to pass and after lunch I’d stood at my office window, lost in fantasies of Jack.
I’d had a fascination for Jack since the first time I’d helped him get started on his research project for work. He was about 25 years older than me, in his late 50’s or maybe more. Older men tend to catch my attention, for the simple fact that they seem comfortable with who they are, and easier to talk with. I’d fallen first for his terrific smile, and the laugh lines that creased his handsome face. Jack’s blue eyes were kind, and he had a rich mellow voice. He was a quiet guy, but friendly, and didn’t seem to even notice the fact that women tend to watch him. Something about that made him even more adorable to me. It led to my dropping flirty hints in my own shy way. Finally, Jack had taken me to dinner
As a date, Jack was sweet and attentive but not smothering. He was patient, but so powerfully seductive that I could not resist the chemistry between us. We’d ended up making out on my porch, and I was so totally lost in what we were doing, that it’s a good thing Jack moved us indoors. The hot sex that followed was something I’d been thinking of all week, as well as the veiled hint he’d left me with. He’d made some quip about restraining me next time, and pleasing me in ways I had yet to experience. Needless to say I was definitely looking forward to him showing up at the library again.
Just as I found my body beginning to respond to the memories alone, Jack’s car pulled up to the curb in front of the library. Goosebumps contracted my nipples, and I felt the beginning of a wonderful lower ache. Affecting a casual air, I watched as he set his brief case on one of the tables. I flashed him a quick smile and strode past, supposedly to shelve some books. Though I didn’t really need to, I used the ladder; hoping he’d notice the stockings I’d worn that day just for him.
Jack glanced up from his work to see what I was doing, and seemed mildly concerned that I might fall off the ladder in my strappy high heels. What he saw seemed to mesmerize him. I covertly watched his gaze fix on black bows at the backs of my shoes, then wander to the tiny black hearts which marched up the back of my stockings to disappear under the hem of my skirt. He cleared his throat, pried his gaze from my hemline and greeted me with a guilty smile, “Anna — pretty as always.” I felt a wicked delight in seeing him struggle for composure.
I smiled and walked to his table. “Why thank you Jack, and you’re looking pretty fine yourself. You need anything?” I could always hope he’d say “Only you, right now”.
Instead, he watched my hand stroking the table. I was filled with erotic thoughts of that hand on private places – places such as Jack’s cock, hard as the table but covered in velvety skin. “Well actually, I’m all set for now,” he said. “I’ve still got a pile of last week’s stuff to sort though.” I don’t think he even realized he was stroking the buttons on his briefcase with his thumb. They were about the size of my nipples, and the mental comparison was making me crazy. Goosebumps slid up my spine; my nipple erections went up another notch, just watching him.
“Let me know if you change your mind,” I blushed, and back up the ladder I went to grab another useless pile of books. For the next 2 hours I worked on shelving the day’s books and saved a few bottom-shelf items for last. Every time I found my gaze straying to Jack, he was smiling at me. That slow sexy grin was almost too much to bear. Would closing time ever come? I strode down the aisle and squatted daintily on my tiptoes to place books on the bottom shelf. Determined to give him something to think about, I paused there just long enough to put on a little show, just for Jack.
I watched him from the corner of my eye as I bent down and oh-so-slowly smoothed my stockings and adjusted the garters. Thank goodness I was wearing my red sweater with the revealing neckline. I hoped he was getting an eyeful and maybe the start of a raging hardon. I really hoped he was planning revenge. I made sure to smooth my black skirt over my hips and make playful eye contact as I licked my lips. Jack’s mouth hung open for a fraction of a second before he shifted in his seat and rearranged his work area.
Near closing time, Jack packed up his research and headed for the front counter. The library lights were flickering out in every other aisle, as a last call for checkout was made on the intercom. He leaned over the edge of the counter to peek into my office and saw me standing at my desk with my back to him. Spritzing on a bit of perfume, I pulled the clip from my hair, then grabbed my purse and coat as I headed to the counter. I quickly scanned his card and the books, then shut down the computer and reached for my stuff to leave. We were the last two people in the building. I figured there would be an awkward moment of hopeful anticipation, but didn’t even have time to finish that thought.
Jack smiled as he reached for my hand, and planted a soft kiss on the inside of my wrist. “So, did you think I wouldn’t notice the fire burning in your eyes, and the way you teased me all afternoon?” He edged around the counter, pulled me closer and nuzzled my hair. He smelled great, and felt like a slice of pure heaven as he hugged me close. I could feel the warmth of his chest through his thin dress shirt, my breasts crushed against him. This was what I’d dreamed of all week. He kissed me, gently at first …then deeper, with barely restrained passion. His tongue mated with mine, mock strokes of what I wanted him to do elsewhere. I loved the way he kissed: always teasing, waiting for my response, and pulling back a bit to make me want more. My hands clung desperately to his back, and my breath was coming quicker already. Every stroke of his tongue was slow, and I wanted to feel it lower — much lower. Just the thought of him licking my pussy was enough to dampen my panties!
Jack held me close and whispered into my hair, “Let me take you home? I want to taste all of you!” I could feel the length of his cock against my stomach, sending a mental picture I could remember in amazing detail.
“Oh Jack, I’m kind of in a fix. You see, my brother is painting my living room today, and won’t be gone until around 8 o’clock tonight!” Frustrated, I leaned my forehead against his chest. Jack’s mind started to whirl with several quick thoughts. He mumbled that his place was out of the question; it was half an hour away.
Slowly he raised my chin with his knuckles and kissed me, a wicked grin crossing his face as he waltzed my backward into my office. I started to laughingly protest, “Not HERE Jack, no way!” He seared my mouth with a silencing kiss. One hand slid under my skirt and stroked my creamy thigh above the garter. I felt his warm hand ease it’s way higher. A single finger slipped past the crotch of my silk panties as he continued kissing me senseless. He teased and stroked in the moisture gathering in my folds. Kiss, stroke; nibble, stroke. I was really hot for him but I just could NOT do this at the library, could I?
Jack’s kiss became more possessive, insistent as my hands made a halfhearted attempt to stop him. I guess I had it coming after teasing him all afternoon. Between the kiss and the fact that his fingers were drenched in my slit, I knew there was no denying how much I wanted him. He shifted a bit and reached his middle finger deeper inside me, sliding his thumb over the hood of my clit. The instant shock sent waves of passion thrumming through my pussy. My hips began riding his fingers, thrusting slowly over and over. My pussy lips felt swollen, and that ache was building fast. Jack’s smile never wavered as he watched my resistance melt away. OK, maybe he was right, and the library isn’t such a bad place to fuck.
Jack continued to kiss and finger me slowly as he guided me backwards into my office and around the desk. With his foot he locked the brake on the chair wheels. He knelt at my feet and reached up to tug off my black lace panties. As he pulled them off I felt his knuckles dragging slowly over my hips and legs, inch by torturous inch. I daintily stepped out of them, taking care to balance, and not catch the lace on my heels. He stood and grabbed the hem of my sweater, slipping it off over my head. I shivered as he kissed the tops of my breasts, and then lifted them to rest atop the cups of my bra. He brushed my nipples softly and gave them a simultaneous light pinch. It pulled desire deep in my womb and I felt the wetness magnify. I moaned and tossed my head back, my hands now stroking his cock through his pants. I was so ready for him! Jack smiled as he reached up to loosen his tie and slip it over his head. He was careful not to undo the knot, harboring secret plans for it.
Leaning into Jack, I struggled with buttons and his zipper. He stilled my hands and whispered against my lips, “Do you trust me?” I instantly recalled the last time he’d said this, and how wonderful things had turned out. All I could do was murmur a breathless, “Yes, Jack, yes!” as I slid my skirt down over my hips.
He slowly turned me around so my back was to the chair, and guided me into it. He tugged my hips close to the front edge of it and leaned me back, kissing me the while. I felt him maneuvering my hands behind the chair, and fastening his tie around my wrists. I was about to panic, but he moved behind the chair and began to kiss my back and the nape of my neck under my hair. It felt so wonderful that I lost all thoughts of true struggle. Nothing mattered but Jack. He slipped the knot close and whispered in my ear between kisses. Words of reassurance reminded me that my restraint was a slipknot; I could escape if I really wanted to.
I was amazed that it was actually quite a turn-on for me, and pictured how I must look sitting naked, hands tied behind my back, breasts on high alert. The leather was cool against my bottom, now decorated with only the black lace of my garter belt. My feelings about that office would never be the same.
Jack’s arms came around me from behind. He teased the soft skin of my breasts with just his fingertips, and his mildly calloused fingers gently abraded my skin. I desperately wanted him to make contact with my nipples, but Jack was a master of slow hands. He continued to tease the rounded tops and soft undersides of my breasts. My breath came haltingly as he finally brushed across the peaks. As each single finger slid across, I felt my nipples popping up harder. Jack chuckled softly in my ear from behind me. He made a second and third pass over my nipples, then captured them simultaneously. The slight pressure was a shock as he rolled both nipples between his fingers. I groaned and leaned my head back against his chest, never wanting him to stop.
Jack began kissing behind my ear. He whispered against my neck, “Anna, you know I would never hurt you, but I think you have problems letting me please you. You deserve this sweetie, and I’m going to taste you fully.”
Closing my eyes, I gave in to the sensations: his fingers masterfully working my nipples, his warm breath on my neck, the cold chair at my back and the definite tiny gush of fluid in my pussy. I knew he was right; this was something I had never experienced, and felt a little shy about. Giving oral sex was a wonderful experience for me, but so far no one had offered to reciprocate. Never had I let anyone get that close, and the thought of Jack being the first was totally making me crazy. I leaned into Jack’s kisses on my neck (his sign that I was OK).
“I want you to know I’ll be gentle. I’ll go slow, and anytime you want me to stop, just say so, OK?”
Lost in sensation, all I could do was nod. He nibbled around my shoulder, and knelt in front of my chair. I thought I would lose my mind when he lapped at my nipples and tugged them gently with his teeth before sucking them vigorously. The ache in my pussy was pulling harder. He knelt on the floor and lifted my foot, kissing my ankle and moving slowly up my leg. I could feel the heat of his breath going higher and higher up the silk stockings: ankle, shin, inside of my knee. By the time he got to my upper thigh and nibbled the creamy flesh exposed there, I was squirming. His rough manly cheek brushed against my pussy lips and I stiffened in anticipation.
Jack paused, asking, “You OK honey?” Eyes shut, I winced. He watched my face, again calling, “Anna?” Struggling to find my voice, all I could think of was how great he made me feel. Though I was so embarrassed, I really wanted to feel his warm mouth at my pussy. Just the anticipation of it was killing me. How could I find the words for this? Jack was just starting to pull away when I panicked and the words came to me. I tipped my hips forward and whispered, “Oh Jack … this is so hard for me … but don’t you DARE stop!”
Jack’s laugh was low and throaty as he brushed his chin across my auburn bush. Soft and well trimmed, it is the same color as my hair, kind of like a little landing strip about two inches wide. He kissed the top of my fuzz … then the middle, and the bottom where it met the hood of my clit. My hips bucked a bit from the intense feeling of the contact and I could feel the wetness soaking my slit.
Jack knew enough about women to realize this was a first for me, and he’d have to be really gentle or I’d experience pain from the intensity. He licked slowly at the outer edges of my pussy lips and breathed warm air across the hood of my clit. I moaned softly, almost a whimper. Jack stroked my inner thighs gently. “It’s OK sweetie, let yourself go. I’ve wanted to taste you for so long. You’re beautiful like this. Open for me, Anna.”
Something in my heart absolutely melted with the sound of his rich mellow voice, commanding me to accept this pleasure. My knees opened wider for him, and I gripped the silk tie that bound my hands. The ache between my legs was growing to mammoth proportions. It spread half way down my thighs, my lower lips feeling swollen and tight. My thigh muscles twitched as his tongue made first contact with my labia. It was so soft and gentle I almost cried. I felt slow soft strokes on the outer lips. It felt warm and wet, and I just had to squeeze my inner muscles to release some of the tension building there. Jack chuckled softly as he kept licking. His flattened tongue licked the full length of my lips, pressing them gently, over and over, with slow, flat licks.
By now I was moaning and my hips were tipping forward to meet every stroke. He was driving me mad! My eyes flew shut as his tongue slid inside my slit and stroked all the way up to my clit, up and back again real slow. It was an extremely strong jolt of pleasure, making me squirm for more. The touch was so soft it almost tickled.
Jack shifted a bit, and the fingers of his right hand moved to spread my lips slowly wider. He pushed up gently and I felt my clit slide out from under its hood. The sudden exposure to the cool air, followed by his hot tongue, was amazing. The soft touch of the tip of his tongue to my clit made me almost fly off the chair.
“Shhh, Anna, it’s OK … I’ll be gentle,” he promised. I could hardly believe I was sitting on my office chair, naked and spread wide, with Jack licking my pussy. What a picture!
He gathered a bit more saliva and gently laved my clit side to side. When he started circles on it I was afraid I would scream. My hips were moving now with every stroke he made. My nipples had ever been so hard. His hand left my thigh, and suddenly he eased a finger just barely inside of my pussy. I could hear the wet sounds as he began stroking inside of me. It was almost unbearable; the combination of his breath and tongue on my clit added to the sweet torture of his finger. My legs raised up on tip toes; I offered him all of me spread wide. Jack added a second finger inside of me … in, out, in, as he licked at me. It was nearly enough friction to send me over the edge.
Jack shifted position, slid his hands under my bottom, and positioned his mouth directly over my clit. He kept his face locked to me as my hips ground into him harder and faster. I was driven to pump even though it wasn’t necessary. Heat spread through my whole body, my clit on fire as he played it with his tongue. Finally I tried to hold it back, but Jack was just too smart. Briefly I thought I was regaining my control, when he formed a mild vacuum with his mouth over my clit and flicked faster with his tongue. I cried out and came so hard my legs squeezed shut tight against his head. Trying to keep them open was futile; the intensity of the climax was thumping away hard, making my legs twitch, until I cried out, “OH Jack, OH FUCK, you’re making me come!”
My body froze its motion as I let the waves of a really great orgasm settle over me. Don’t ask me how Jack knew just when I started to climax, but as I did, he put his tongue flat against my clit and held it there. My clit throbbed against his tongue, making it more wonderful for me. After a moment, he softly kissed the fuzz above my slit, and stiffly stood up with a chuckle.
Breathlessly I slid my hands out of his tie as he moved behind to assist. He helped me to my feet and held me close against his chest, kissing my hair and rubbing my back. I remember snuggling into the warmth of his arms and being totally amazed that Jack’s cock was fully erect against my tummy. What a sweet surprise that this would be as big a turn on for him as it was for me!
Jack’s cock sprang to meet my fingers as I reached between us. I stroked softly at the tip, then reached down to cup his balls. The weight of his balls in my hand was incredible, soft but heavy. Teasing and tugging his scrotum, my nails then trailed ever-so-lightly over the sprinkling of hair on his balls. Finally my hand grasped his shaft fully and rode it from base to tip. I watched as a drop of glistening precum emerged. Jack groaned as fingers slid across the single drop and I bought it to my lips to lick; to taste the saltiness; to tease. Moaning as I licked the tasty treat from my finger, I could feel the ache building again in my pussy, though I was still catching my breath. More than anything, I wanted to concentrate on pleasing Jack.
Kissing my way down over his chest, I stopped to lick his nipples and nip them softly with my lips. Lower and lower I kissed, until I could nuzzle the springy hair surrounding his cock. His private scent was mixed with the clean smell of soap. I knelt and let his beautiful hard cock slide along the side of my face. Drawing back, I kissed the tip. He stroked my hair with one hand.
I took a firm stroking grip at the base of his cock, guided him to my lips and flicked my tongue across the tip. Next came slower licks just on the head, longer and flatter, like I’d give an ice-cream cone. I worked circles around the ridge and then teased again, gently sucking the head. With my other hand I caressed his balls, then tugged them towards me as I took him fully into my mouth. Jack squeezed his eyes shut and tossed his head back with a moan. A single thrust, and I went back to teasing, licking my warm tongue over the wrinkles of his scrotum, then sucking each side into my mouth, caressing his cock as I did. I licked lines from his balls up the shaft, and nibbled the seam along the way. Again I took only the head of his cock into my mouth, nothing more, as my eyes locked with his. I felt a wicked grin coming on as I bobbed on the meaty glans.
A man can only take so much teasing. The next thing I knew, Jack had a firm hold in the hair at the back of my head. He pulled me onto him deeper. Air hissed over his teeth as I took him all the way into my throat. He began to thrust his cock into my mouth, harder and faster. I just love it when a guy helps me out that way. Keeping pace with his movements, I let him show me just what he liked. Flicking my tongue back and forth over the seam on the in-strokes, I would suck softly on each out-stroke. Jack’s cock was totally slick, riding over my lips and teeth easily. I could feel every vein and contour with each stoke sliding in and out, faster, harder.
I remembered how great he’d felt in my pussy. He was magnificent. Now, his cock was getting so hard and thick that I could barely take it all in. I gave it my best effort. As I sucked, my hands rode up and down his thighs, pausing now and then to caress or tug his ball sack. Following the line where cheeks meet legs, I teased the crease of his cheeks with my nails. I loved the feeling of his throbbing cock in my mouth, just waiting to shoot. Jack’s movements slowed, then suddenly stopped as he pulled out of my mouth. He was really close, and to be honest so was I. The whole time I was working his cock; I’d felt the ache in my pussy building again. It wouldn’t take much for me to come a second time.
Jack pulled me up for a passionate kiss, which tasted faintly of my own juices. I was embarrassed for about a fraction of a second, but the memory of how that flavor got there was sweet. He pulled me down with him onto the carpet. He lay on his back and guided me to kneel over him, with my face at his cock, and my pussy over his face. I’d seen this in porn films I secretly watched, but it was nothing I ever thought I’d be doing!
His springy cock was dancing right below my lips, so I took it in and began to thrust. As Jack licked my slit, he slid two fingers inside me again, gently rubbing my favorite spot. My hips began to rock with him. Soon I found my thrusts on his cock timed to his fingers in my pussy. His warm mouth was planted over my clit and I was going wild! His fingers pumped my pussy gently but rapidly. I increased my speed on his cock to match.
As I worked Jack’s beautiful cock, I felt the tips of my pert nipples scraping on his stomach. Faster and wilder I stroked, with his guidance. Jack’s free hand reached around me to lock my hips closer to his face. Arching my back to give him better access, I was riding, pumping, grinding urgently into his face. His tongue was dancing over my clit, which again started to throb. Just then, I felt his balls draw up a bit, and he stiffened deep in my mouth as his cock began to shoot. It sent me over the edge, and my clit felt like it exploded in his mouth with great aching throbs. Again he held his tongue flat and let me come against it. My clit throbbed over and over. I moaned on his cock as I struggled to swallow every shooting spurt he delivered. It jetted against the back of my throat, and pooled on my waiting tongue. It was an awesome deposit; Jack must have been saving all week.
Turning to face Jack, after a passionate thank-you-kiss, I cuddled on his chest. He was staring up at the ceiling and stroking my back, planting kisses now and then in my hair. I traced lazy circles on his stomach and thought how crazy I was for this guy. He was incredible! That’s when Jack said, “I think we have a small problem.” It seemed to me there could be no problem, assuming he felt half as good as I did. His next movement showed me otherwise, as he pointed at the security camera in the corner of my office. My hand flew to cover my mouth and I started to giggle. How on earth was I going to get the security guy to release the tape to me? We were eventually to work it out … but that’s another story.