Terry Loses Her Virginity

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

"Dr. Liz, call Olivia and tell her that she is the maid of honor at her best friend's wedding at 8:00 P.M. Dr Emily, you will give away the bride. Dr. Liz you are the matron of honor. Get someone to play the minister and get enough guests to seat them every three seats in the theater. Also get the indoor golf cart and tie cans on it and write unseemly things on it. I'll drive Terry from the Theater around that long hall up to Master Suite 9 for the honeymoon. I also need a sexy lingerie set in black or maroon in Olivia's size. I will explain later."

Terry and I are hungry, "Could the chef cut the ribeye in thin strips and cover it in sauteed onions and sprinkle it with crusted parmesan? We both would like a salad. Thousand for me and ranch for my bride. Terry says garlic bread and fried green beans and I concur. The young lady, and myself would like orange sherbet for desert if he has it."

Dr. Emily piped in, "Anything else? Dave how long have you known about this?"

I said Dr. Emily, "I promise I only told Terry to write her fantasy for losing her virginity after we had lunch today and I am reading this for the first time. She was crying when I picked her up. This addresses why she was crying. She really has grown up and we are all going to have to treat her like an adult going forward."

She said, "Thank you Dave, we will have Master Suite 9 ready for you in 30 minutes."

I ran over to Dr. Liz's office and had them copy Terry's 5 pages so they could work on it too, while I was reading it. I was told that Nurse Julia had just arrived and she wanted to know what her role in the evening's proceedings would be.

"Tell Julia, I owe her big time for rushing over here from the airport! I know she's tired. After the wedding she will accompany us to the 'honeymoon suite'. Tell her to wear one of her Mistress outfits. She will remain with us until after the hymen issue is resolved. Once I penetrate Terry, I'll have Nurse Julia examine her and make sure everything is fine. Then she will leave us alone for the night. Tell Dr. Liz I will use Olivia to hold Terry and comfort her during the penetration. Once I get in, we will send Olivia out as well. This is Terry's night, but you see on page three of her fantasy she asked for Olivia for the first part."

While Terry and I sat in the Clinic I took the magnifying eye set the gynecologist had and got Terry back in the gyno chair spread wide in the stirrups. With the magnifier and the lights on I could see the extra skin at the lower portion of her vagina. It looked normal. I could also see as clear as day the second band of skin across the opening about 2/3's of the way up toward her clit. I said, "Terry, this is amazing. I have never seen this before. I can see them both, and I can also see how wet you are up close and personal."

About that time her mother said over the P.A., "Dave, you have the P.A. system on, not the intercom between these offices. I think everyone in the Club now knows you're playing with the gynecology instruments in the Clinic with my daughter."

"Sorry," I said. "But Club ask Dr. Emily to show everyone this in one of her classes. This is fascinating! It really is!"

I think they turned off the P.A. system!

Dr. Emily opened the door and said, "Master Suite 9 is ready. Why don't you two go on up before you break something in here." We went on up and everything we asked for was in the suite. As soon as we got the door closed there was a knock at the door. Our supper was brought to us in the suite. We ate, showered, and dressed.

When we arrived at the Theater at 8:10 everything was set. Dr. Emily walked her daughter down the aisle and we were married in the mock ceremony. After I kissed the bride and we left the theater. The golf cart was parked in the hall. It had all kind of sexual things written on it. Terry really got a kick out of it. I drove down the halls and into the elevator and then down another hall to Master Suite 9. Terry kissed and hugged her mother. Terry, Olivia, Julia and myself went in and locked the door.

I said Terry, "Are you sure you don't want the camera running to just record this? It doesn't have to be live where anyone else can see?"

Olivia looked at her and said, "Please, please record everything." Terry looked at me with questioning eyes.

I said, "Julia knows how to set the cameras to 'record only' so that no one outside this room can see us. Tech can put a code on the files so it can't be copied without you entering a code. That way you can have a DVD if you want. I can see you and Olivia sitting on the bed in your PJ's next week eating popcorn and watching what we did tonight. In two weeks, we can do the same for Olivia if she wants to."

Terry said, "Yeah, record it but don't let anyone see us tonight."

We had Julia put on some music and we danced. Terry had me dance a few with Olivia as well.

The next time I danced with Terry I caressed her neck and back. I fondled her rear which she really got turned on by. I dropped her veil to the floor and ran my fingers through her hair over and over. I kissed her softly all over and then kissed her on the lips. She was breathing harder and faster and started whispering things in my ears. I undid the snaps on her dress and with the Bridal lingerie underneath the dress slid off her and to the floor. In the candlelight her body was magnificent.

I could tell Olivia was feeling out of place and said, "Olivia come over her and help me with my tie, please. When you get it off blindfold Terry with it." They both gasped. "Now Olivia undo my belt and take it off." They were both so hot I could smell their excitement. "Now use my belt to tie your best friend's hands behind her back." Once Terry was blindfolded and wrists were bound, I said, "Olivia now undress me down to my underwear and then whisper in Terry's ear what I have on. I lost my shirt, shoes and socks, and then pants.

Olivia gasped and said above a whisper, "Terry he has on sheer panties just like yours. I can see his huge cock right through them. Our moms were telling the truth."

Terry was so wet it was running down her legs through the thin sheer panties. Terry said, Mr. Dave, Please do me now!"

I said, "not yet, not yet. I'm going to keep you aroused but not allow you to cum! After I keep you on the edge for an hour or longer you will crave penetration and beg me to fuck you. It's then that you will be so focused on those sensations, and overwhelmed by sheer desire you will only hurt for a moment when I break through that hymen and bring you into womanhood."

Terry said, "Mr. Dave, I'm already there! I want you to throw me down on the bed rip off my panties and do me right now! Please Mr. Dave."

I caressed her face softly in my hands, kissed and the licked her lips and whispered in her ear, "Remember when your mother told you I knew things that young men didn't even know existed yet? Remember when she told you I would play your body like a musical instrument?"

"Yes, I do, but I'm ready now!"

"Terry do you trust me? Have I ever done anything harmful to you? Have I ever hurt you?

Terry replied, "No sir. You have looked out for me ever since we met, but I need it now!"

"Didn't I get you out of that clinic downstairs and don't you still have all your hair down there? Haven't I promised to give you a night you will never forget?

"Yes sir," she said just above a whisper.

Remember I told you at lunch that I couldn't wait to get into those panties, but I will wait until you are ready. Believe me I'm ready now, but you are not. I don't want you to remember this night as the night that Mr. Dave got so excited that he plunged into me and really hurt me because he wanted in my panties. I want you to remember this as the night that Mr. Dave built up your sexual tension over and over and over until your body was so ready for his cock that you hardly remember the hymen issue.

After I take your virginity, I will have Julia check and make sure you are alright. If you are, she will leave the room and Olivia will leave the suite. Then I will carry you into the bathroom and bath you and wash your lovely hair in the soft candlelight. After that, adult young lady, I will do anything to you and for you that you ask of me. If you trust me and wait, I'll tie you up like you asked at lunch, and I'll even let you tie me up and do anything you wish to me. Do we have a deal?"

"Yes, Oh yes, it's a deal! How will I know when I am ready?

"That's the thing, you are young and this is your first time. You won't know, but I will. That's why your mother wanted you to do this with an older man and not a young stud that who would just try and ram it home and hurt you because he was thinking of himself, not you."

"Mr. Dave, "How can you just wait and wait with a young girl tied and begging you to just do it?"

"Honey, it's not easy! I want to do it right now too! But this is all about you and not me. I will get my turn later."

Olivia spoke up for the first time, "Wow! I've had so many boys at school try and get me to have sex with them. They all say that I got them hot and bothered and that I need to give them relief. They make it my fault and my obligation, too. They are all jerks!. Are you going to be like this with me, Mr. Dave?"

"Absolutely, but it will be totally different. You don't have this hymen issue. I understand you lost yours' sliding into second base in a softball game." She whispered into Terry's ear and Terry nodded and then said to me.

"Mr. Dave can Olivia stay after nurse Julia leaves? Maybe even sleep with us all night?"

"Terry, there won't be much sleeping after nurse Julia leaves. I think this is going to be all night sex."

Terry said, "Well, what I meant to say, as an adult young lady, can Olivia stay and play bondage with us all night?"

"Girls, Sorry, adult ladies, I have two conditions. Both are not negotiable! Dr. Liz must say it's OK for Olivia to stay. You two must promise that if Olivia stays under no circumstances is, she to be penetrated by me or you."

Terry looked confused and blurted out, "I can't penetrate Olivia, even if she begs."

"Oh, really? Don't you two tell me that you were never tempted to fuck each other with those strap-on dildos or vibrators you found in your mother's playrooms while you were playing bondage. That dresser over in the corner has more toys that both of your moms' playrooms."

If we can all keep that promise, Olivia can stay if her mom agrees. To be crude again, I'll can't wait to get into those panties in 2 weeks, just not tonight."

While Olivia called her mother, I bent over and licked up Terry's thighs and nibbled on her pussy. I let her get really close and then stopped.

Olivia said, "Mom said I could stay if it was OK with Terry and you, but said under no circumstance was I to be penetrated with anything tonight."

"So, are you staying?" I said.

"Yes sir, thank you."

"Don't thank me yet. I will put a chastity belt on you if you attempt to get penetrated. "Get those cloths off now, if you are staying."

"Everything?" She said

"Just strip down to that sexy lingerie set you have on."

I removed the tie from Terry's eyes so she could see her best friend strip in front of us. Terry said even that turned her on and asked if she was weird. I told her if that did not excite her, she would be weird. I asked her if she really wanted to play hard bondage and she said yes. I motioned to Julia and she brought a wooden stock from the second room of the suite. I positioned it facing the bed and put her feet through the ankle holes and locked it. I bent her at the waist and put her hands and neck thru the holes in the upper stocks and locked it.

I moved behind her and slipped my cock into her panties and teased her pussy from behind. She was very wet and slick. She moaned and moaned. I came around and sat on the bed and told Olivia to come and lick Terry juices from my cock. I let her get me close to cumming and pulled out. Slick sticky fluid was sliding down Terry's legs.

I said, "Now Olivia, go clean up Terry's legs and pussy."

Watching that almost got me again but I managed not to cum. While Olivia cleaned up Terry, I could see Olivia's satin panties were literally sagging with sticky stringy cum. I laid on my back on the bed in front of Terry and told Olivia to face sit me in front of her best friend. I brought her to three orgasms and was a mess myself. I made her lick her juices from my face and then said, "Your mother told me that you girls like licking a man's cum from your mother's panties. Is that so?"

"Yes," they both said and blushed red. I asked what their mothers said about it and they replied, "They both said we were normal."

I had Olivia kneel on all fours on the bed and I spread her legs with my hands as I knelt between her legs and pulled her panties down just enough to slip my cock inside that satin and started pumping her on the outside. She tried to get it in her but I grabbed her hands and held her perfectly still.

I said abruptly, "If you attempt that again, I will lock a chastity belt on you and keep the key with me until your night in two weeks."

Mr. Dave, "I'm sorry, give me one more chance, please, please."

"Agreed. Olivia, I'm going to make you squirt without even penetrating that tight pussy of yours."

I alternated between slapping my cock on her clit and rubbing it up and down the outside of her slit. In four or five minutes she started squirting and the warm pussy juice and the friction of my cock inside her satin panties pushed me over the edge. When I coated her with hot semen she squirted and moaned.

I got off the bed and said, "Pull those panties up tight." I stood up and with Terry in the stocks her face was cock level. "Terry, lick my cum and Olivia's cum off my cock."

I had Olivia help me get Terry out of the stocks and tied her spread eagle on the bed. Maybe it was because this was her first time but Terry seem to have a running steam of juices flowing from her restricted pussy. I had Olivia face sit Terry with panties full of my cum. I put clamps on Terry's nipples and asked if she felt it in her pussy.

She said, "I do, why do I feel it in my pussy the harder you clamp my nipples?"

I said, "The nerve endings go to the same place in the brain. It's even more intense with men. I'll let you clamp my nipples later with some stronger than those if you want to. Terry do you know the safe word is 'safe word'? She never answered.

I told Olivia we are getting close. Terry kept sucking the cum from Olivia's panties and was panting pretty hard. I knelt between Terry's legs and slid my penis into those thin sheer panties and started rubbing her on the outside but avoided her clit. Terry started thrashing pulling on her restraints and screaming over and over she was ready. I did it several times and backed off." I wanted her just on the edge.

I had Olivia remove her panties and put them on Terry's face. I whispered in Terry's ear," I'm going to put a rubber gag in your mouth. It will help if you bite down on it when I penetrate you. I will put the gag in so it pushes the cum filled panties into your mouth and makes the crotch tight over your nose. That should keep you turned on. When I get you ready the next time suck on the panties and take very deep breaths. The scent of semen releases a hormone in most women that makes them go crazy with desire."

"Before I penetrate you, Olivia is going to put her legs across your chest above and below your breasts to minimize your thrashing. I'm going to tie your knees to some rings on the side of the bed and keep your ankles fastened to the bedpost but free your wrists. With your ankles and knees tied wide apart it will reduce your thrashing and I won't have to hit a moving target. When Olivia puts her legs across you and grips your hands you hold on like your life depended on it. If the pain becomes unbearable and you want to stop and rest then let go of her hands. I will not stop, no matter how much you scream, unless you let go of Olivia's hands! You won't be able to say 'safeword' with a gag in your mouth."

"OK, Mr. Dave. I'll try to hold on no matter what! You are going to try and break my hymen in one shot, aren't you?"

"You catch on fast my young bride. When I watched that video of Niki and Mark again last night it hit me that it hurt her the same each time. If we take 6 attempts, like they did, I'm going to hurt you so bad 6 separate times. If I get in on the first attempt, I will only hurt you once. Then we can spend the rest of the night doing things that feel really good. I think you are going to scream loud, but I won't stop unless you let go of Olivia's hands."

Nurse Julia stuck her head into the bedroom and said, "Mr. Dave are you sure you want her gagged when you go for it."

I said, "Julia I had surgery in a hospital hall once without an anesthetic and biting down on a hat was the only thing that helped me get over the pain. I told the doctor once he cut into me with the scalpel not to stop unless I let go of that hat. I didn't let go and it was over on a couple of minutes. We got the ball gag for her to bite on, the grabbing of the Olivia's hands for dear life, and Olivia's legs across her chest to keep her still."

She said, "You saw how thick it is when you were playing with the instruments in the clinic. Are you sure?"

Nurse Julia, "I'm not sure of anything, but after I watched that video over and over, I realized they didn't have Niki really ready and he hurt her 6 times really bad. I want to do this one time. Unless she lets go of Olivia's hands, once I feel the hymen, I'm going to lean into her very hard and not let up."

I went back to Terry and said, "It's time to get into those panties. I'm going to lick and suck your pussy for several minutes with Olivia. You will start feeling your juices running all down you. When you are ready, your pussy will actually open out like a flower and elongate. (Ask your mom about it tomorrow) When I see those things happen Olivia will hold you down, grab your hands and I will shift up and penetrate you all at once as hard as I can. None of this, put it in a little and back off over and over. That will hurt just as much, only several times. If I have to hurt you to get it in, I only want to hurt you once."

"You can scream into that gag, bite down on it, and wrestle with Olivia's hands. DO NOT LET GO OF OLIVIA'S HANDS UNLESS IT'S SO BAD YOU HAVE TO STOP! Listen now, Once I'm in I will stop and be totally still. It's going to hurt for a couple of minutes and maybe even sting a lot. After a couple of minutes, you are going feel wonderful and 'full' since it will be the first time you have ever had a penis in your vagina. Once it starts feeling good, I'll screw you until you cum vaginally and I will cum. You're going to feel hot semen flood your pussy. You might pass out. That's, OK. That's why I have nurse Julia."

We will both rest and Julia check you out. Once she sees that you are OK, she will leave us for the night. I will bath you and wash your hair and anything else you want. After that, I'll do anything you want me to do."

"Ready? This buildup will take about 8 to 10 minutes. Holding Olivia's hands and biting on that gag will help you keep from tensing up. Nurse Julia will use cool wash clothes on your forehead and monitor us closely."

Mr. Dave, "I'm ready.

Nurse Julia came into the bedroom with some cold wash cloths and stood at the head of the bed.

"Olivia, please get Terry's panties off. Tease her with them, wash her with them, lick her everywhere you can think of."

We licked and sucked on Terry 8 or 9 times, backing off just before she started to cum. The next time when her pussy flowered out and elongated, I moved up and placed my penis right in her vagina opening. I could feel the head of my penis touch her hymen.