Deja Vu

Story Info
Tom relives losing his virginity - twice over.
5.2k words
4.45
21.1k
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I was 42 when my marriage fell apart. I'm Tom Sinclair, and I was a senior manager in a large government office in the north of England. After my wife told me she was leaving me for a man fifteen years her junior I felt pretty depressed. I no longer had any family in the area, and a lot of our mutual friends tended to avoid me, too embarrassed to look me in the eye, since they'd all known for months that she was shagging her fitness coach. It was partly my fault, with all the late evenings I'd been working; but that didn't make it any easier to take. I felt I had to get away, and a few weeks after she moved out I found a golden opportunity in the staff magazine.

A vacancy had come up in South London for a manager in my department. What made the idea particularly attractive was that it was the office where I'd had my first Civil Service job. I was 19 and at university at the time, and the post was something to do between the end of term and Christmas, to bring in a bit of extra cash before I spent a suffocating festive break back up north with my parents. Even though the job had lasted only a few weeks, it was a time I remembered fondly. Of course, more than 20 years on there wouldn't be anyone still at that office who knew me but, even so, it was in a nice part of London and it would get me away from my home town and the pitying looks I was getting from everyone I knew.

My regional manager was surprised I was applying for the post, as it was a bit of a comedown from the more senior position I held, but he supported my application and within days my transfer was confirmed. I travelled down south on a Thursday, found a flat to rent for a reasonable price on the Friday, and the following Monday I rolled into the new office. My new assistant manager, Sally, greeted me and gave me a quick tour of the office, introducing me to a couple of dozen mostly young staff whose names I had no chance of remembering at that point. We'd reached the last room in the building when I got the surprise of my life. As we entered, a raucous voice I remembered only too well rang out: "'Ello Tommy boy, I heard you was rejoining us."

I stared in disbelief -- I could scarcely credit that Karen Watts was still in the office, in fact still at the same desk in the same room where she'd worked with me 23 years earlier. When I was there as a Christmas temp, Karen had been the office character. She was one of those people it's impossible to ignore: a mass of big blonde locks (her Dynasty look, she called it), a salon-tanned face that was attractive without being pretty, knockers the size of watermelons, and gorgeous legs that she displayed with skirts rather shorter than a married mother twice my age might have been expected to wear. Her voice could have served as a coastal foghorn, she told bluer jokes than any of the men in the office, and her filthy laugh made the cawing of crows sound refined by comparison.

Karen was over 60 now, the formerly peroxide hair was white, but just as big, as were the boobs that threatened to tumble out of her blouse. She giggled when she saw the stunned look on my face. "It's nice to see you too Tommy. I was thinking of finally takin' me pension, but I put it off when I heard you was comin' back to rock my boat." The three other staff members in the room sniggered, Sally tried to hide her smile, and I felt my face burning bright pink. I stammered something about it being great to see Karen again, and how surprised I was that she was still there, then scuttled off to my office, to the sound of her laugh billowing down the corridor.

I spent the rest of the morning with Sally profiling the area our office covered, going over stats and so on. When she excused herself for lunch I slumped back in my chair, dazed at the notion that Karen was still there. She was one rank more senior than when I had known her before, but I would have expected her to have moved on by now, or indeed to have retired. Staring into space, I thought back to that earlier time, when Duran Duran ruled the pop charts, and Thatcher and Reagan ruled the world. The reason for my shock was that it was thanks to Karen that my memories of working there before were so warm...

I had been given the desk directly opposite Karen, in a room with three other staff members: Ronnie, a sharp-suited 30-something who liked to boast about his sexual conquests, Ado, a quiet black guy, and Michelle, about my age but far more worldly, tall and skinny with dishwater hair, purple lips and huge bangle ear-rings that parrots could have perched on. I was a young lad from Yorkshire, in the big city only a few months, shy, and ready to blush at the drop of a hat. Because I was so quiet and nervous on my first day, Karen nicknamed me 'Smiler', and amused herself and the others by mercilessly winding me up. On my second day she came into work wearing a vest that did little to conceal her huge tits, and I couldn't help glancing up at her every few minutes. I realised she'd caught me at it when, every time I looked, she yawned and stretched, thrusting her boobs out like a ship's figurehead.

Mid-morning, Karen sashayed over to my desk, big hips swaying, and parked her generous bum on the corner of it. Her black-stockinged leg was inches from me -- I could actually see the bare flesh of her thigh under her skirt -- and her boobs were directly in my eye line. The other three all subtly sat back in their chairs, grinning in anticipation of the entertainment to come. Casually swinging her leg, Karen asked, "So Tommy boy, anyone had a nibble at your cherry yet?"

As Ronnie and Michelle almost exploded trying to control their snorts of laughter, the fierce red glow that leapt onto my cheeks told Karen the answer to that one. Grinning wickedly, she leaned closer to me; her half-exposed knockers were only a tongue's length from my face, and her sickly sweet perfume was overpowering. I felt as if I was shrivelling up in embarrassment as she glanced down at my lap and cooed, "Ooh, you're being a bit selfish keeping that tent pole to yourself sweetheart." That was it for Ronnie -- he collapsed on his desk, tears rolling down his cheeks. Even Ado had a broad grin. Karen moved her face so close to me that her lips brushed my ear and, in a stage whisper that was probably heard three streets away, murmured, "You wanna take young Michelle there down the pub. A couple of Bacardi and Cokes, she'll soon show you what that's for."

As the men collapsed in helpless mirth, Michelle shrieked with laughter and screamed "Karen!", throwing a pencil at her. When she thought Karen wasn't looking though, Michelle gave me a toothy grin and a lascivious wink, rolling her tongue suggestively around her lips. I couldn't look at any of them the rest of the day without turning scarlet, and at 4.30 Carl Lewis wouldn't have beaten me in my sprint out of the door for the bus to my digs. It can't be true that wanking makes you blind, otherwise I'd have needed a guide dog by the time I got out of bed the next morning!

When she wasn't taking the piss out of me, Karen was genuinely friendly and helpful, and I quickly warmed to her. Dealing with her helped me to build up my general self-confidence, and after a couple of weeks I was capable of answering back when she tried to embarrass me, and our relationship became almost flirty. Michelle, on the other hand, used to roll her eyes and tut as if it was the most pathetic thing she'd ever seen, and started to snap at me. At the time I didn't really think about why.

My last week in the office coincided with the Christmas party. The party was due to start at five o'clock on the Friday, but the booze started flowing during the morning. At one point Karen wandered over to my desk, a wine glass in her hand and a cheeky grin on her face. My chair had wheels, and she pulled it out from under my desk and sat on my lap with an arm round my neck, pushing her boobs into my face. "You feeling Christmassy, Tommy boy?" she grinned, while our colleagues watched with amusement. She started to grind her bum firmly into my groin, causing an instant erection. I realised the others couldn't see what was happening below desk level and, with unusual boldness, I placed a hand on Karen's stocking-clad knee. She didn't even flinch, just kept grinning and grinding. Nervously I crept my hand slowly under her skirt and up her leg. My fingers actually rested on her bare thigh before she leapt off me and, chortling, swayed back to her own desk.

By mid-afternoon everyone other than me had pretty much stopped working. I was alone in our room doing some filing when I became aware of a cloying scent, and looked up to see Michele standing close to me; very close. She gave me a smile, and said, "I'm sorry I've been ratty with you the last couple of weeks Tom. I've been having a bad time with my boyfriend, but we've split up now. Later on you can get me those Bacardi and Cokes if you like. You know, the ones Karen mentioned that time." I gasped as I felt her hand rub firmly across my trouser fly. Then she turned away and walked out of the room, grinning back at me over her shoulder. In all honesty I really didn't fancy Michelle; but despite Karen's prick teasing it seemed the only offer on the table, and I resolved that before the day was out I would have finally lost my cherry.

At the party I did the rounds of my colleagues, saying my farewells and getting a few hugs and handshakes. Mid-evening, after a couple of drinks, I made my way to the toilet. On the way back an arm reached out of an alcove and grabbed my tie, and Karen pulled me into the small space with her. It was so small that our bodies were pressed together. Breathing wine fumes into my face, she giggled and started to rub her crotch against mine. Then she whispered, "I know Michelle's got plans to give you one tonight. Be honest, Tommy -- wouldn't you rather get your first fuck from an experienced older woman?" Suddenly too nervous to speak, I nodded. I hesitantly cupped a hand over her breast, half of which was exposed by her low-cut dress, and stroked the bare flesh. Suddenly, with a roar of laughter she pushed me away and crowed, "Yeah, I'll bet you would, you randy little sod." Then she walked back towards the party. Just before she entered the room she glanced back at me and said, quietly, "Well, let's see how the evening goes, shall we?"

After a couple of hours a dozen or so of us decided to head for the pub. The place was packed, but by sheer weight of numbers we bullied our way to a group of corner tables. Karen disappeared to the loo, and when she returned she had found a hair band from somewhere and lodged a sprig of mistletoes in it, hanging over her head. There was great hilarity as she made her way around the blokes snogging and groping each in turn. Finally she squeezed herself onto the bench where I was sitting, right next to me. "Okay Tommy, your turn." Before I could react she'd mashed her lips to mine, her hand pressing on the back of my head. Her tongue thrust into my mouth as I found myself locked in the sexiest kiss I'd ever experienced. On my other side, I heard Michelle make a disgusted sound.

We had a good time in the pub, but gradually the numbers dwindled. Towards the end of the evening I was still sitting with one woman on either side of me, both of them pretty drunk. Michelle was draped across my right shoulder, her tongue stuck in my ear; Karen was on my left, blowing in my other ear, her fingers stroking my inner thigh inches from my straining cock and her boobs pressed firmly against my arm. The colleagues who remained, all men, found the situation hilarious. To say I felt hot and uncomfortable was something of an understatement. Michelle was clearly less than happy with the situation too, and she leaned across me and said pointedly, "Karen, isn't it time you headed off home? You know, to your husband, the one you married?"

Karen replied, "Nah, I've told Mickey to do the nightshift this week, so I can bring me toyboy home with me", and doubled up with laughter. Michelle stared at her furiously, then started nibbling my earlobe and tugging on my arm, trying to drag me out of her rival's clutches. I could scarcely believe two women seemed to be fighting over me. Once Karen recovered from her laughing fit she started licking my other ear. One hand was still at the top of my leg, and she slid the other between my shirt buttons and started caressing my bare chest with her fingers. Making sure Michelle heard, she giggled, "Blimey Tommy, are you this hairy all over?"

As long, blood red fingernails began to tweak my nipple I couldn't help myself; I started to turn towards her, presenting my back to Michelle as Karen's lips slipped from my ear and across my cheek, towards my mouth. Michelle's reaction was instant: with a scream of fury she leapt to her feet and snarled, "Why don't you fuck off, you disgusting, evil old bitch?" Karen's only reaction was to slide her tongue into the corner of my mouth and start stroking it around inside, her eyes fixed on Michelle. With a wail of frustration, Michelle hurtled towards the door and out into the night.

I felt bad about Michelle. After all, I was never likely to see her again, and I hadn't wanted to hurt her. I started to get up and go after her, but Karen held me back. Nuzzling her nose into my cheek, she whispered, "Leave her love. You don't need her tonight, I promise." Then she sat back and, more brightly, said, "Well young Tommy, are you goin' to be a gentleman and walk a lady to her cab?" Dragging me after her, Karen made her way to the door, kissing and groping the remaining stragglers from our party.

The night air outside was frigid compared to the hot, beery atmosphere in the pub, and a light drizzle was falling. Thankfully we had to wait only a few seconds for a taxi, and Karen clambered in, pulling me after her. As the cab set off I suddenly felt very nervous at being with Karen. After all, she was a real man-eater twice my age. She immediately snuggled up to me and started kissing me again, her tongue slipping between my lips and stroking along my teeth. At the same time, her hand dropped into my lap and started stroking my rampant cock through my trousers.

Cautiously, I placed a hand on one of Karen's boobs. She arched her back, pressing it more firmly into my grasp. Emboldened by that, I reached down the neck of her dress and scooped my hand around her tit, inside her bra, feeling her spongy nipple pressing against my palm. She moaned appreciatively, and pushed her tongue deeper into my mouth. I sensed the cabbie watching us in his rear view mirror, but by then I couldn't have cared less if we'd been in the middle of Piccadilly Circus in the rush hour. Deciding to go for broke, I eased the shoulder straps of Karen's dress and bra down her arm, exposing her tit, and, pulling away from her mouth, applied my lips to her nipple. She hugged me to her and chuckled, "You dirty little fucker."

I felt as if I was in a dream, sitting in the back of a taxi with a married woman's boob in my mouth, her hand rubbing my dick, while the driver watched us at it. Totally brazen by that point, I slipped my hand up Karen's dress and curled my fingers around the silky knickers which covered her crotch. I was just trying to worm a finger inside them when she gripped my wrist and giggled, "Easy tiger, I don't want you popping your cork before I even get you home."

How I didn't cum in my pants in that cab I have no idea; I can only imagine that the amount of booze I'd drunk dulled my senses just enough to allow me to hold off. When we reached Karen's street, she half fell out of the car, clutching her coat round her to hide her exposed breast, while I fumbled out money for the driver. He gave me a grin and a wink, and muttered, "All the best son -- give 'er one for me while you're at it." We tottered up the garden path, Karen unlocked the door of her tiny house, and there I was -- minutes from sex for the first time, with a gorgeous, erotic, outrageous woman not much younger than my mother. After weeks of fantasising about it, it was actually, really, going to happen.

Almost shyly, Karen took my hand and led me up a narrow staircase to her bedroom. There she stood before me, her hands on my shoulders, and smiled at me. She asked softly, "So Tom, are you really still a virgin?" I swallowed nervously and nodded. With surprising tenderness, she stroked my fringe off my forehead, and said, "God, I don't think I've ever had a virgin before. Okay sweetheart, just relax." Never taking her eyes off mine, she slowly unbuttoned my shirt and peeled it off me. She trailed her fingernails through my chest hair, then dropped her hands to my waist. Efficiently undoing my belt and fly, she knelt in front of me and ease the trousers and my underpants down to my ankles. Karen gently pressed her hand to my belly and, my knees giving way, I sank into a sitting position on the bed. She winked at me and whispered, "All right darlin', 'ere we go."

I watched in amazement as her blonde head dipped towards me and her big sensuous lips closed over the tip of my cock. Her mouth slipped down my length, her tongue stroking my flesh, and I shuddered as the most glorious feelings of pleasure radiated through my loins. Karen's forearms rested on my thighs, and one hand cupped my balls while the other wrapped firmly round the stem of my prick. After probably no more than a minute I felt my muscles spasming, then I erupted a fountain of jizz into her mouth. Karen kept licking and sucking at me until she had milked every last drop of my cum from me. Feeling guilty that I hadn't managed to last longer I started to apologise, but she quieted me. "That's all right honey, I knew that'd be a quickie. Just means you'll keep going longer when we really get down to it."

It was a chilly night and, almost like a loving mother, Karen eased me under the bedclothes before switching off the light and quickly stripping off her clothes. In the moonlight through her bedroom window her magnificent body looked sliver-blue: I gazed at her heavy breasts, her nipples big enough to cause their own shadows on her skin, her slim waist, her wide hips and her plump thighs, surprised to see that her pubic area was completely shaved of hair. She scuttled across the room to join me in the bed, and cuddled me to her. Holding my first naked woman was an incredible experience. Her cheek rubbed against mine, her boobs squashed against my chest, and her thighs intertwined with mine. She was cold and I squeezed her tightly, rubbing my hands up and down her back. One of my hands dropped to her fleshy bum, and I began kneading it, like dough.

Karen rolled on top of me and we kissed tenderly, our tongues playing with each other like dogs frolicking together in the park. Then she moved back to my side and gently pushed my head down to her chest. Again I suckled on her breasts, licking my way between them as she sighed and stroked my hair. My hand eased down her body and between her legs. I was surprised how easily my fingers slipped inside her pussy. It felt incredible, hot, wet and clinging, and I began to push three fingers in and out of her. She groaned at that and husked, "Fuck Tom, you're good at this. If you're ready, darlin', I need you to fuck me now."

God, was I ready. I rolled her onto her back and moved my body between her legs. She grabbed my buttocks in a vice-like grip, pulled upwards with her hands, and for the first time my cock entered a woman's vagina. I lay still for a moment, just enjoying the wonderful feeling around my prick, then as Karen pulled at me again I started to fuck her, with short, fast stabs. She put a hand on my shoulder and whispered, "Easy baby, take it a bit slower." Desperate to please her I changed to long, slow strokes, which clearly had the desired effect. She started to rub her legs up and down mine, and express her enjoyment in words. "Ohhh yeah, that's it, fuck, fuck, yeah baby, that's so gooood." She'd been right about sucking me off before, I was able to keep going for a while, even after Karen whimpered and I felt her pussy tighten around me, and a fresh flood of juice surge from her. She continued to grip and caress my bum, and as I got closer to cumming I gradually increased my speed, finally releasing a river of spunk into her as she sighed happily.

12