Sisterly Support

The company conference is often a source of disappointment where sex is concerned. Going away to a hotel with work colleagues for several days raises unrealistic expectations. Fantasies of kinky sex with that secretary in accounts with the nose ring; or picking up a bit of strange at the hotel bar only to discover her husband waiting back in their room wants to watch you fuck her; all belong on these pages, not in real life. In reality, the evening ends with a group of drunk blokes in suits dancing in a club; being avoided by every young woman, except the poor waitress who has to take their orders.

That's why I avoided our last conference until our new sales director ordered me to attend as part of my CPD (Continuous Professional Development). To keep my license as a life insurance advisor, I had to attend several sessions and get the ticks. Because I was late booking, our company hotel was full, so I had to find another. That piece of luck led to a remarkable sexual experience that changed my life.

My hotel was pleasantly tucked away from the big places catering for the Brighton conference crowd. I was enjoying a quiet drink in the bar, reluctantly preparing for informal/mandatory evening drinks with our sales director at his hotel ten minutes' walk away. I noticed two older ladies in a corner. One looked distressed. Instinct gleaned from my job made me go over. On closer inspection, the blond one could have won many glamorous granny competitions with her face and figure. The brunette, sniffing back her tears, was cuddly and plain.

I smiled at them. "I noticed your friend's distress. Can I help?"

Blondie gave me a critical look, then realised my concern was genuine. "That's kind of you, but my sister is just a bit teary. We will be ok."

I smiled. "I'm sorry for your loss." I turned to leave.

Tearful looked surprised. "How did you know?"

I gave her my look of professional condolence. "Forgive me for intruding. I'm a life insurance advisor. I'm the guy couples see when they take out policies, and widows see when we pay up. You get a sense of bereavement."

They weighed me up for a moment before Blondie concluded I was telling the truth. "John's been gone two years. Rose wanted to come here to scatter his ashes. It's where they met. Would you join us for a drink? I could use a hand cheering her up. I'm Sheila, by the way." Her smile said I would not refuse. She extended a slim hand with beautiful red nails. She noticed my interest as I took it.

I've always had a thing for older women. Sheila sensed that. I stayed for one drink out of politeness. By the second, it was because I was enjoying their company. Rose cheered up, and she had a lovely smile. She was more reserved than her sister, and her attractiveness came from within. Sheila's charms were more obvious, and I wondered if she'd had a boob job. She had a pair of tits that would grace a woman half her age. I was in danger of missing my appointment.

"Ladies I'm afraid I will have to love you and leave you. If I miss drinks with my boss, he will make my life a misery."

Rose was a bit worse for drink and grabbed my hand. "Don't go yet Tim. We were going to invite you to join us for dinner, weren't we Sheila?"

Sheila fell in. "I thought Tim was a gentleman, but he's standing us up." She had a sexy pout.

I'm sure she could hear my cock straining. "If you are here tomorrow evening ladies, I'm all yours?" They nodded. "Then it's a date."

Sheila winked at me. "Did you hear that, Rosie? You've got a date."

Rose was a bit slow on the uptake. "Oh no, you must come too Sheila. A date, honestly." She reddened.

Sheila laughed. "It's been so long since you've been on a date, I'll have to come along...for Tim's safety."

Rosie hid her face in her hands.

I bade them goodnight. I knew they were watching my arse as I left, so I put my hand behind me. Rosie laughed and Sheila wolf whistled. I was looking forward to dinner tomorrow. It was my reward for the false mateyness and old jokes the rest of my evening had in store for me.

#

When I scanned the bar, I missed them in my first sweep. I looked again and recognised two glammed up women smiling at me. They had taken the date literally. They stood as I approached. Sheila wore a tight black pencil skirt that ended just above the knees. Her red silk blouse tucked into it. A wide patent leather black belt emphasised her curves. She stood eye level to me and I noticed black stiletto slingbacks and sheer stockings. She's stolen the outfit straight from my sexy secretary fantasy. My smile told her it was a hit.

Rosie was a revelation. She wore a wrap-around navy-blue dress in a clingy material. Her figure was almost voluptuous. Her brown hair was up with two curls at her ears. She looked ten years younger. Her face reddened as I took it all in.

"Wow, you both look gorgeous. Is this really your sister, Sheila?" I took Rosie's hand.

Rosie blushed. "I told you it's too much Sheila. I should never have let you talk me into buying something so clingy. I'm going back upstairs to change."

Sheila explained. "We've had a pamper in the beauty parlour. Does Tim's face say it's too much, Rosie?"

She saw my reaction and could not find words, so she just shook her head.

"Let's eat ladies. You've given me quite an appetite." I offered them an arm each, and we headed to the restaurant. "Look at Johnny Big Potatoes with his two girlfriends. I hear Frenchmen take their wife and mistress out together. Very civilised."

"Ha! You wish," said Sheila.

Rosie almost tripped, and I caught her. "How do women walk in these shoes? I must have been mad to buy them."

I looked down at her strappy white high-heeled sandals. "Ah, there's your mistake Rosie, they are not walking shoes."

Sheila leaned behind my back and stage whispered, "You're wearing fuck me shoes. Not sensible ones like these." She lifted her foot for me to admire. Her heels were even higher.

Rosie looked at us. I can't speak for Sheila, but Rosie's expression of fright and excitement had me hard.

My interest in their shoes had them both playing footsie with me over dinner. They teased me mercilessly as I tried to eat. I suspect Sheila was an old hand, but Rosie was a keen student. We quickly cantered through my marriage to and divorce from my university sweetheart and Sheila's first marriage to a car salesman. Rosie said she never understood what her sister saw in him. She almost choked on her soup when Sheila ferreted in her clutch bag. "He had a big cock. I think I've still got a picture of it."

Rosie looked at her open mouthed. "I can never tell when she is joking, I'm so unworldly."

I said it was sweet and Sheila scoffed and said her sister would be prey in the dating jungle.

Rosie took umbrage. "No, I won't. I might meet a someone nice like Tim." Her nervous smile was enchanting. I took her hand and kissed it gallantly. Rosie did a little shiver.

Sheila gave me a look. "Stop it Tim, you'll have her coming at the dinner table."

Rosie found another shade of red. When she recovered, she confessed John had been her first and only lover through courtship and marriage. "Forty years with the same man. Who does that nowadays? I've been curious, of course, but happy to live vicariously through Sheila's escapades."

Sheila blushed, then got her own back. "Tim, you have a moral duty to fuck this woman well."

"Sheila! Tim may not want--"

"Don't be so dense Rosie. It's written all over his face. Tim has an older woman fixation, a big boobs fixation, a high heels fixation, and a fantasy involving sleeping with two women."

I nodded at Rosie. "Your sister is gifted, but she left out the most important one." I leaned forward to whispered, forcing them to do the same and distracting me with their cleavages. "I am obsessed with the idea of sharing a bed with sisters.

"Ha!" Sheila folded her arms under her substantial bust. "I knew it. They are all the same. If we were friends, he'd be thinking he'd have to choose one of us, but because we're sisters Tim's going for broke. When is he likely to get this lucky again?"

"I rest my case, Rosie." I winked at her.

Rosie looked flustered. "I've never... I've never had someone else in the room when me and John were making love." She whispered the last bit.

Sheila snorted. "That's not for your husband's want of trying. Christ, the number of times he propositioned me. Especially after Eric bought me these tits for my birthday. John said a threesome would spice things up between the two of you." She realised too late she'd spoken her sister's unnamed fear.

Rosie looked tearful. "I know John was not happy with me in that department. But he was no great shakes himself. He was happy for me do all the work until he was ready to climb on."

Sheila leaned over me and gave her sister a hug of apology.

I took her hand. "I know what I want for afters. A big helping of Rosie, followed by a second helping of Rosie, but I'll save space for a portion of Sheila."

Sheila took her sister's hand and stood up. "Okay, greedy guts. Get the bill while me and Rosie go to the powder room for girls talk."

I wasn't sure what confidences they exchanged in there, but when we got into the small four-person lift, Rosie surprised me by pulling my head down and kissing me. Her tongue went right into my mouth and I felt her boobs, thighs and little belly moulded against my body. I grabbed the cheeks of her lovely round arse and nuzzled my head in her shoulder. When I broke away, Rosie's eyes reflected my passion. I only realised Sheila was there when her slim hand slid between us and grasped my cock.

"You see Rosie. Tim is not shy. He's twice as excited by you taking the initiative. Feel this. I don't think his cock can get any harder." Sheila took Rosie hand and wrapped it around my cock with hers on top to stop Rosie pulling away. Rosie bit her lip and sighed.

"We agreed Rosie will go first. Just make sure you save some for me lover." Sheila pulled my head towards hers and kissed me. Those big tits were against my chest. Her firm thighs trying to straddle mine in her tight skirt. I grabbed her arse and pulled her tighter. She raked the back of my calf with her heel and I moaned.

Sheila pulled away and pressed the button. "Let's go before there is nothing left for either of us, shall we?"

#

I my room Rosie had another wobble. I'd left them at the small table in my suite while I got ice for our drinks from the fridge. The sisters were in conversation when I returned.

"Rosie wants to wear a blindfold when you fuck her Tim."

I looked at Shelia for an explanation. Her stare told her sister to provide the answer. Rosie's words came reluctantly.

"You're only 41 Tim and I'm 62. When you take off my dress and the corset thing that's holding me all in, you'll see my bumps and wrinkles. I don't want to see your disappointment."

In Rosie's voice, I heard years of critical comments from her unsympathetic husband. I took her hands and made her stand up. I kissed the two creases in her brow, the little crow's feet at the corner of her eyes and mouth and the crease at the top of her cleavage.

She sighed and hugged me. "There's plenty more where they came from," she muffled into my chest.

"Then they'll get the same treatment," I said. There'll be no blindfolds for that purpose Rosie."

I looked over at Sheila who saw my interest in her sister was genuine. She mouthed thank you.

I wanted to change the mood. "If you and Sheila are up for it, I've another use for a blindfold." Rosie looked confused.

Sheila smiled. "Tim wants us to play a sex game Rosie. Okay Johnnie Big Potatoes, let's see what you've got."

I was sure Sheila was no stranger to a blindfold, but moments later sat back-to-back holding her sister's hands with one of my curtain tiebacks circling both their heads, must have been a novelty for her. "How long have you been planning this one, Tim?"

"Oh, since I was at school, Sheila. The game is called `Guess what I'm doing to your sister? You get three guesses before I swap. "

I started with Rosie. Gentle, silent kisses on her lips and neck. My fingers trailing down her cleavage. She moaned. "Oh Tim, that's lovely, you're making me so wet."

Sheila's guesses were wide of the mark. "He's fingering you, Rosie. Tim's rubbing his cock over your face. He's got your tits out."

"No, he's not Sheila! Tim's seducing me."

Sheila huffed, so I moved round to her.

"You didn't guess correctly, but you'll get a turn, anyway. "I removed her shoe. Sheila had sexy feet. Her red nails shone through the sheer black nylon. I sucked her toes.

Sheila squirmed on the chair. "How did you know? Oh God." My hand slid to the back of her knee and stroked as she tried to open her legs in her tight skirt. I kissed her mouth and Sheila sucked my tongue down her throat. Her lips made slurping sounds.

"Sheila! You said I could suck his cock first, you promised." Rosie was put out.

We managed another round of guesses before Rosie came as I pulled her nipples through her dress. I declared her the winner, even though all their guesses were wrong.

Sheila pulled the blindfold off. She was edgy and miffed at not coming. She wanted revenge.

"Timothy is a terrible man, Rosie. Plying two ladies old enough to be his mother with drink. Then luring us to his room, blindfolding us, and using us for his sexual gratification. That's what I'll tell the police. Unless he'll take his punishment."

Sheila's mock stern voice almost had me for a moment. Rosie was slower on the uptake. "Don't call the police Sheila." Then it dawned on her. "Oh, it's another sex game. You two are clever."

"Rose, take his clothes off while I decide an appropriate punishment." Sheila knew she'd soon have me in the state I'd left her. An eye for an eye.

Rosie undid my shirt and got a surprise. "Sheila, Tim's got no hair. His chest is smooth, and his back is too. It's lovely. He feels like a young lad." Rosie rubbed her hands across my chest and put her cheek to it.

Sheila raised an eyebrow and adopted a stern school teacher tone. "What's the meaning of this boy, are you a pervert?"

My cock twitched in appreciation of her ad libbing skills. I fell into my part. "No miss. I went for a massage to relieve an old shoulder injury. I looked at the menu and asked what a BSC was. They told me I'd feel ten years younger after treatment. But they didn't tell me about the pain."

Rosie was puzzled. "What does he mean Sheila. What's a BSC?"

Sheila laughed. "Remember how you complained when they sorted out your fanny forest in the beauty parlour this morning? Tim's gone one better and had his back, sack and crack waxed hairless as well as his chest. Take his trousers off. We'll see if they did a good job."

Rosie got on her knees and fumbled with my belt. I slowed her hands down. Eventually my trousers were loose, and she pulled them and my boxers down in one go. My cock sprang up, its head slicked in pre-cum.

Sheila leaned forward to inspect. "Not bad, Tim looks like a kid with a big cock."

"Well, I think it's a lovely cock." Rosie held it and licked up and down its length before swallowing me almost to the balls. I looked at Sheila surprised by Rosie's superb technique. Sheila's face was a mixture of surprise and envy. Rosie came up for air. "John made me suck his cock. Forced me until I could take it all in. It was not as nice as this. His had lots of hair and sweaty balls."

I held her chin up. "This is lovely Rosie. It's the best cock sucking I've ever had." I hadn't meant it as a challenge.

Sheila got on her knees next to her sister and took my cock from her hand. "Let me try his hairless dick." She gave me a look that would have had a man on a short fuse spurting before he'd ever reached her lips. Her tongue teased the underside of my helmet and her nails scratched the back of my bare sack. I groaned; Sheila knew I was on the edge. What she said next was inspired.

"Timothy, can you remember the first time your hairless dick got this hard?" I mumbled yes. "Tell me about it and I'll let you cum." Sheila held the base of my cock, trapping my jizz. It was agony and ecstasy.

My mind went back to a familiar memory. "My Auntie Joan taught me to swim when I was a kid. I'd pretend to drown, and she'd clutch me up to her big bosom and rescue me. It made me tingle."

Sheila nodded sagely at Rosie. "Did you ever see her naked Timothy?" She was wanking me gently now. Rosie watched the two of us. I closed my eyes, and I moaned at the vivid memory. My cock grew another inch in Sheila's hand.

"Auntie Joan went for a shower one day and didn't close the bathroom door because of the steam. I hid in the linen cupboard, spying through the slats. I watched her dry her big boobs and big bum. She put her foot on the stool while she towelled her fleshy fanny and I gasped. She left the bathroom with a giggle. I'm sure she knew I was there."

Sheila cupped my hairless balls and massaged them gently. "You've always liked big women, haven't you Tim? Women with big boobs and bums? Women like Rosie and me?"

"Yes, yes. Please Sheila, let me cum." I felt lips sliding along my cock until they reached the base. The head was in her throat. Moments later, I came painfully and copiously. Shot after shot. When I opened my eyes, it was Rosie's mouth around my cock, with an overflow of spunk dribbling down her chin.

Sheila looked triumphant. "You've always wanted a woman like Rosie, haven't you Tim?"

I whimpered yes.

They lay me on the bed between them to recover.

Rosie was in awe of her sister's prescience. "How did you know Sheila?"

Sheila smiled. "Tim's not the first younger man I've enjoyed an evening with. Some are just curious and move on once they've tried it. But others are hooked because of a deep-seated desire arising from an incident in their youth. Often before they were sexually active. Isn't that so, Tim?"

I nodded in admission. "You can read my mind Sheila. You know it is."

Sheila got up with a smug smile. "I'm going to the loo. Why don't you two get better acquainted?"

I was not ready to go again, but I wanted to enjoy Rosie's body. I stood her up and undid the single side bow securing her wrap over dress and slipped it from her shoulders. She was not as big as Auntie Joan, but Rosie had the same wonderful curves constrained by her white lace corset underwear. I stood beheld her, counting as I unfastened the twenty hooks and eyes. Rosie's large breasts spilled into my hands. Long brown nipples. Like the breasts I'd hungered for all those years ago. I turned her around and fed them into my mouth while she held my head and sighed.

I got on my knees and inhaled deeply.

"Oh no, you can smell my pussy, Tim. I'm sorry. It's just that I'm so wet after coming."

"Why are you apologising?"

"John didn't like the smell, he wouldn't go there."

"John was an idiot." I pulled her knickers off and her wonderful smell was in my nostrils. Her pussy was like Auntie Joan's. A prominent mound and deep cleft. I pressed her knees apart and examined her fleshy pinkness.

"Oh god Tim, you're looking at me like a doctor."

"I'd be struck off for this." I pulled her arse towards me and buried my nose in her gash. Soon it was coated in her juice. I held her open and tongued her clit.

Rosie held my head to her pussy as she came. "Oh god Tim, this is wonderful. He'd never do this to me, the bastard. You can do this whenever you want." She was shaking unsteadily on her high heels.

I slid two fingers inside and found her g-spot. Rosie's next orgasm was a knock-out blow. Her legs gave way, and I lay her on the bed. She was so ready for the fucking I hoped I could still give her. I tugged my semi. A hand reached around to replace mine, then a body was against my back. Sheila had taken her top clothes off. My bare back was sensitive since waxing. I felt the rough lace edge of her bra, the sharpness of her suspender in my thigh, and the heat of her pussy on my arse. I tried to turn around, but she stopped me and tugged harder on my cock.