tagFirst TimeOne Last Chance

One Last Chance


Anne and David had met on the internet about three years ago, their friendship took on deeper levels and sooner than expected David tried to convince his “sexy Babybear” as he called her into a little late night phone sex. Having strong convictions Anne didn’t immediately give in and rather she never had. But, David stayed and continued talking to her for a little over half a year with no phone sex just their intimate online discussions. And then just as abruptly as they had started, David vanished offline.

Six months ago he suddenly reappeared and dropped the bombshell, he was about to be married within the year. June 14th would be his day of wedded bliss and after that there would be no further contact with his sexy Babybear. After many nights of talking through messenger they discovered that they did both have intense feelings toward each other and had not been able to reveal them to the other one until their hands were forced at this point.

Anne had not known if he had been serious before about meeting simply because she had never even given in and allowed him to phone her. Now she was trying desperately to find a way to meet him and see if she could find happiness. But alas, the dear man had morals and wouldn’t risk throwing away his pending nuptials for a one night stand, or even risk it blossoming into something more.

The weekend prior to his wedding David unlike most upcoming bachelors would be at a business meeting in Washington D.C. So he wouldn’t be having a bachelor party after all he would be in meetings from early morning until late even Thursday and Friday. Saturday his last meeting was at 10:30 am., so he would have the rest of the day to himself to relax and just prepare for his return flight to Minnesota on Sunday afternoon.

The strange thing was Anne had also been deemed a representative for her workplace to go to D.C. to a conference and bring back as much info as possible for a new union. She knew that David was going to be there and where he was staying but she didn’t know if she would brave her own fears and make contact.

Over time during their discussions Anne had told him exactly what she looked like. She was 32, 5'1" and had hazel eyes. A little on the heavy side she told him all he needed to know was that she was a bbw with large 44dd’s. During their more sexual discussions she had also revealed that she trimmed her pubic region short but not shaved or waxed. She was also light complected, had a few freckles and shoulder length brown curly hair.

David was quite the contrast thought, he was 5'10", clean shaven about 200 pounds, with dark hair and eyes, as well as being Asian-American. He was from Minnesota and she could imagine his sexy accent if they should meet.

In all their shared times online he had described what he thought was sexy to her. A strong preference for women in sexy bras and underwear instead of little teddies and garters. He was into oral sex and slightly submissive. More in a playful nature though, he was into the foreplay aspect of sex greatly and although he had experienced sex had never given or received anal play at all.

Anne thought about all this as she packed for her flight, she placed several matching underwear sets in her garment bag and even had gone out and bought a black one which she knew was his favorite color. She wondered if she would even have the nerve to approach him but would decide that when the time came. She was preparing herself for anything and packed a few other special items as well.

As she left out of Boston’s Logan airport she thought about all the things she had shared with David, her sexy Asian stud thus far. She had told him how she was raised Roman Catholic and that she had been devout in her religion. Then in her early 20's she had put on a little weight and her self image had declined. She couldn’t imagine anyone wanting to touch her or even the possibility that she would be able to be nude with anyone for fear of ridicule. She had one boyfriend while she was 21 which lasted about a week for one reason or another and then when she was 24 she was almost raped. This had finalized her thoughts that since she had waited this long she would remain a virgin until marriage. Now finding herself at the age of 32 and having no male proposals for marriage and no boyfriend, she thought she may just be content giving her virginity to a man that would be kind, she knew well, and had some feelings for.

David was a bit apprehensive as his flight took off from St.Paul /Minneapolis International airport. He had only spoken to his sexy Babybear a few times lately and yet he knew something was amiss. He knew that somehow she was coming to terms with the impending nuptials he was about to go through with and that she would lose all contact with him forever afterwards. His bride to be was possessive and she checked up on him constantly, probably even now she was trying to get into his email accounts and see who he had been talking to and what he was up to. He had arranged to stay in a quaint Bed & Breakfast Inn in the capital once he arrived there. He hadn’t wanted the standard rooms he had searched for one with a jacuzzi and fireplace with a view overlooking the Potomac River. As he landed, he went to get his rental car and then drove off after retrieving his luggage.

Anne stood in awe after her plane had landed. Here she was waiting in baggage claim when a tall Asian male walked right past her. At once from his descriptions of himself alone she knew it was him. And as much as she wanted to reach right out and touch his shoulder and let him know she was there she couldn’t do a thing. She was frozen with fear, fear and arousal. She couldn’t bring herself to reveal herself now because what if he rejected her here and now. Then her whole trip would be ruined and she would be distraught throw the seminars and lectures and meetings she had to attend. Anne slipped back from the crowd and waited until the man left before gathering up her things and getting into her own rental car. She drove to the B&B she knew David was staying at and then checked in.

Two unrestful days later, and playing many a game of viewing but not being seen with David, Anne booted up her laptop. She scrolled through her naughty alter ego account on yahoo and allowed herself to search for any messages David may have sent. As soon as the messenger service popped up she held her breath. “Hello Sexy Babybear,” came a quick response from David.

Anne breathed a slow sigh of contentment and then responded, “Well hello sexy stranger, how’s your trip going?” “Fine so far Babybear, but I do wish I had told you to just come and meet me here this weekend.”

“I do too sexy boy, but, I know you would have regrets if I had,” she typed back eagerly waiting his next response.

“Well, yes, I would have, but, I think we could have handled it. I mean I have lay here awake both nights thinking about you and touched myself while I imagined the things we would have done.”

“David, what would you say if I told you I could be there in a few hours?”

“Come to me sexy Babybear then and we will share one night of passion.”

“David, sexy boy, what room are you in?” she asked trembling as she typed.

“LOL. I am in room 417 facing the water. But silly you know you won’t come here, we have never even talked on the phone. I know that you would love to meet but don’t waste the money even if you can get a flight by the time you get here I would be passed out I’m sure.”

“What if I could make it in the next fifteen minutes sexy?”

“I’d tell you to come then and I’ll leave the door unlocked.”

“Wishful thinking sexy David, but unlock the door and wait, just in case, oh the phone is ringing, I have to go but leave that door unlocked for the next fifteen minutes.”

Anne quickly signed off the laptop and checked herself in the mirror, thank god she had showered and changed into her black underwear prior to logging on. Now all she needed was to slip on a light dress and walk around the building to his room. This was it now or never she told herself.

Thirteen minutes later she tried the doorknob to room 417, it turned unencumbered by a lock. She held her breath as she pushed open the door and walked in. David sat on the bed in his boxer’s looking in disbelief at the woman before him. He had imagined her so many times but now here she was in the flesh a few feet from him.

Neither spoke, they just drifted towards one another. The electricity between them was nearly visible and the lust and passion in the room was almost claustrophobic. That it would have been if they were rational but neither of them could be right now. David spun so that his legs hung over the bed and Anne walked towards him. Those last few steps were the hardest in her life.

“Don’t speak sexy David,” she said, “if you do I may turn and run from here with fear. Just kiss me, hold me, make love to me please. I have to know how you feel inside me. I have to share myself with you and this is the last chance I may ever have to do that.”

David nodded and stood up, he placed his hands on her shoulders and leaned down and kissed her deeply, all thoughts of his fiancee’ fled from his mind in that instant and he knew that Anne was offering him the most treasured thing she could, herself and her virginity.

He lowered one strap and kissed her shoulder and trailed his kisses down her arm as the strap was pulled free. He then did the same to the other side before he bared her bra clad chest. He looked up as the black bra was exposed and smiled. He knew she wore this strapless black bra for him and he was honored. He kissed the swell of her breasts and down into the valley before sliding up the other breast with his lips.

His touch was soft, unhurried and full of passion. He was looking at her every few seconds like a child presented with that last unopened box on Christmas morning, the one that always holds the most precious present. His fingers ran up the tender exposed neck of Anne and he knew that no matter what else happened he would be sharing his bed with her tonight.

Anne had never done more than kiss a man, and those had been fleeting at that. No one had seen her nude, or touched her breasts, or slipped a finger into her soft, wet opening. Now she was ready and David wasn’t in a rush he was exploring her one inch at a time. She knew she had made the right decision no matter what the outcome would be after this liaison

“David, sexy, take down my bra and suck my nipples please, suck your sexy Babybear’s nipples.”

David shuddered, here she was baring herself to him, offering up all she had and yet remembered that he had a slight submissive side and was toying with it as much as she could. He reached out and unhooked the front latches on the bra and then cupped the two big breasts in his hand. His pink tongue slipped from his mouth and he circled one of the nipples feeling it grow erect beneath his tongue. As he did this his body pressed against hers and he could feel the searing heat radiating from her body.

Shivers rushed through Anne as she felt David’s tongue teasing her nipple, she had made the right decision and she was already soaking her little black panties now and he hadn’t even touched her down there. She would give him a moment more and then direct his attention elsewhere on her body.

David sucked Anne’s other nipple and then stopped and pulled away, teasing her. He ran one hand up under her dress and brushed the fabric of her panties he pressed his fingers into the wet folds as far as the panties would let him and then withdrew quickly. His lips were still wrapped around one nipple and he sucked hard pulling it into his mouth and sucking, nibbling and running his tongue over it.

Anne had received all the foreplay she needed at this point. “David, sexy David, lay back on the bed,” she instructed.

David hopped up on the bed and lie back waiting for whatever his sexy Babybear had in mind next. She turned to the little radio on the night stand and turned on some slow music and dimmed the lights. She then turned her back to him and pushed her dress down over her hips and stepped out of them. In the next instant David was staring at the silky black panties and then just her bare flesh. She was giggling and nervous but she had always wanted to do a little strip for him and this was that chance after all. Anne took a deep breath and then climbed up the bed and knelt between his legs.

“Lift your ass sexy boy,” she commanded.

David lifted up and as his shorts were pulled down his erection sprung free. Anne had never seen a man’s penis in the flesh and had never sucked on one either but no seeing as she had overcome the first thing she was determined to accomplish the second. She lowered her lips without a word and kissed the head of his cock. It had a salty droplet of pre-cum on the tip but that wouldn’t turn her away now. She was horny and willing to please him in anyway he had expressed desire to her in the past.

“Sexy Babybear,” David started.

Anne reached up and put a finger to his lips silencing him as she lowered her mouth an inch at a time over his throbbing organ. Her tongue swirled around his cock and she did gag a few times but she was still turned on and going to please him this way a bit longer. As she sucked his cock little by little her fingers ran their nails over his scrotum and the other hands fingers were softly rimming his puckered anus. She knew he might like this but she was not ready to push harder yet. Anne slurped and sucked at his manhood until he was clutching the sheets in his fists and then his fingers touched the top of her head.

Anne pulled away and slid up his body kissing her way up. As she got near his mouth she felt the pulsing penis between her legs bobbing against the wet lips of her sex. God she wanted him inside her but she wanted him on top this first time. “David, spin around go down on your Babybear please, and then as I suck that pretty cock of yours I want you to get me ready to be made love to. Bare with me I will only need a few minutes.”

David moaned as he slid out and spun around over her. “Babybear, oh sexy Babybear, it would be my pleasure.”

His tongue and fingers immediately were between her legs and she had soon found herself with a mouthful of his flesh again. The feeling of his tongue on her clit and his fingers just probing the depths without breaking her hymen felt exquisite. She didn’t know how much longer she could hold out. That’s when David pulled away. He couldn’t take the teasing any longer.

“Anne, sexy Babybear, I have to have you now. Please let me make love to you.”

Anne nodded and David slipped his penis between her legs. He reached between them and guided the head of his shaft inside the fleshy folds of her love hole and pushed until he reached the barrier of her virginity. Anne bit her lip and drug her nails down his back, “Do it David, make me yours, make love to me. Now!”

David withdrew an inch or two and then pushed his cock in hard and fast, tearing away her hymen and plunging in to the hilt. “Oh baby are you ok, my sexy little Babybear?” he asked, as he held still inside her.

“Yes,” she said with a smile, “I am ok it just hurts a little, I’m ready if you are to continue lover.”

David slowly withdrew and then slipped back in again pushing deep and slow, he leaned down to kiss her every few strokes and then other times would just nibble on her erect nipples. His palms flat on the bed made his arm muscles look enormous to her and she would kiss them as he leaned into her harder.

Their bodies finally joined, she had given him all she had to offer and now they were making sweet, slow, passionate love. In the next few minutes she ranged emotions from pain, lust, orgasmic bliss to love. They were sharing a deep intimacy that she had been incapable of completing before tonight. “David,” she said between kisses, “I love you.”

David didn’t respond at first he just continued to swivel his hips and touch her in places she had never been touched before. He knew he loved her but couldn’t find the words just yet. He wanted her on top and slipped from her body and pulled her over him.

As Anne lowered herself over his cock and felt him probed her depths again she also felt his lips and teeth on her nipples, he was once again teasing her. His hand dropped to her clit and rubbed it as she rode him, her big breasts bobbing in his face as he suckled each nipple. His other hand was toying with her ass and she wondered if he had any intentions of taking her there. She wasn’t sure if she could allow that but knew that if that was his request she would more than likely give in.

David pumped his cock hard up into Anne and she felt her first tingles deep inside, she was about to experience her first orgasm from intercourse. David sensed this as she panted and moaned and rode him faster and faster.

“Anne, I’m going to cum too baby,” he moaned.

Anne rode him through her own orgasm and just as he started to spurt deep inside her she hopped off and wrapped her breasts around his cock and let him pump between them. She lapped at the pulsing head as he shot load after load of cum into the air and her mouth.

They were both still ravenous but couldn’t find the energy to do more than cuddle right away. They lay there and talk throughout the night, and in the middle of the night she woke up to feeling David licking her tight asshole. She pressed back against his tongue and welcomed the exploration. “Yes, David do it baby, take my virgin ass to tonight.”

David reached inside the dresser drawer and pulled out some vaseline, he rubbed it on his cock and then around the rim of her puckered opening. In that time she relaxed and allowed him to probe a little with his fingers. She knew he would be gentle but was still scared.

David slid behind her on his knees and spread her ass cheeks slowly. As the head neared her asshole she shivered in anticipation and pushed back, the head of his cock slipped easily inside with all the lube and at once he pushed deep inside.

“Oh sexy D, that feels so naughty and good,” Anne cried out. Her hips were already bucking and she felt the tremendous orgasm building.

“Babybear, I can’t hold off much longer baby, you’re just so tight and sexy that I have to cum soon.”

“Do it now sexy, in my ass or pull out and shoot it all over my ass god I don’t care just fuck me hard and cum.”

David rammed in over and over his hips pounding her ass as he took her this way. A few short strokes later and he was breathing in gasps and shooting his second load of cum for the night. He pulled out and jerked his cock over her ass watching the creamy white semen dribble down the crack of her big sexy ass.

Anne waited till he was finished and then stood up, she led him to the shower and there they kissed and fondled before stepping out and hopping into the jacuzzi. The evening had been perfect, and she would now know that at least he would always remember her. For she had given him her virginity and would always linger in his mind.

In the morning Anne awoke to a full breakfast and a smiling David, “Now where do we go from here?” he asked.

“Only time will tell, David, only time will tell.”

Report Story

byMaster_Vassago© 0 comments/ 56333 views/ 1 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments  - Click here to add a comment to this story

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: