Polyamory Ch. 12: Debra Gets Fucked

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Debra loses her virginity with a romantic fucking.
9.2k words
4.69
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Part 13 of the 27 part series

Updated 06/09/2023
Created 03/07/2019
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Chapter 12

"Debra Gets Truly Fucked"

I woke once more before the women and decided to go home to shower and shave my neck. I thought I'd go to a barber to get my hair and beard trimmed for tonight. On my way out I picked up my backpack and saw a bag with a note penned to it. "Hank, wear this tonight."

I just picked it up and waited until I got home to look. It was a pair of slacks, a Van Hussen button down collar, pink shirt, and a sports coat. The pants were navy blue. The jacket was light blue, maybe baby blue. There was a pair of men's bikini underwear. Well, maybe you could call it that. There was very little to them.

I laid it all out, shaved my neck, took a shower and dressed. When I got out, I saw my phone screen lit up and checked it. A text from Debra, "Gladys and I missed you this morning. She and I send our love."

Then another before I finished the first, "One rule for today. No cumming. At least no masturbation. Guess we can't blame a person for a spontaneous one. We'll do our best not to have one of those either." The text was followed by a very erotic emoji.

I texted back, "One rule. If you do orgasm spontaneously you have to tell me immediately via text."

A few minutes went by and then a text, "We agree to rule."

I wondered how that would go.

The day of anticipation for tonight dragged on. I did fine with my classes but we have no Friday afternoon classes so I was more or less finished. I went to the barber shop I occasionally went to and had the barber trim my hair and beard. I like the barber I think because she is a friendly and somewhat talkative person. She was an avowed lesbian and told anyone who wanted to know. I asked her if she had found the woman of her dreams and she told me no and asked me the same question.

I said, "Give me a minute." I thought about how to best answer the question. Finally, I asked, "If I tell you the truth, you promise not to spread it around? It's not that I am embarrassed or anything, but the answer is sort of unusual."

"There is a pact between barber and customer like that between lawyer and client. However, if I am called into court there is no protection like lawyer client privilege," she said beginning to laugh.

She had a nice laugh. "OK, then, I have found two women of my dreams. One I think you know and the other I doubt you do. In fact, we are moving in together soon."

She slapped my arm and said, "Get out!" moving to see if she could tell by my face if it was true. "You're not putting me on are you?"

"Nope!"

"OK, spill. Who is it I know?"

"Gladys."

She covered her mouth with her hands and just said, "No! Finally!"

"What do you mean, 'Finally!'"

"We've known she had a thing for you for a while maybe six months. She just didn't want to act on it because she didn't think you'd be into letting her have a woman lover also. So who is the other person? A woman I suppose."

"Yes, she works in the dean's office. She is quite lovely. I guess you could say I robbed her from fundamentalism. She and Gladys have also fallen in love. So here we are. We are moving into a nice house together to explore our relationship and figure it out."

"So you are going to try polyamory?"

"Yep, and tonight is a special night. I probably shouldn't tell you this."

"You can't stop there."

So I told her that Debra was a virgin who only started on pills last Saturday so tonight is the first time it was safe to have vaginal intercourse. When I said that, she said, "Why the distinction?" almost before she got the question out she got a horrified look on her face and then a big grin with hands held out in a sort of "I can't believe this" gesture. "You fucked her ass."

"Really, now! That's a bit undignified."

"What me saying it or you doing it?"

"Maybe both. But yes. I've done both of them several times and last night Debra did me."

"Oh, my God, we got to stop or I am going to cum right here."

She quickly returned to my hair and beard. "So what do you think about the election?"

We talked about politics and how screwed up Florida is until she was finished. She said, "OK, Hank, I think you are suitable for deflowering a virgin."

I suppressed laughing and said, "Really, that's not delicate" trying my best to sound serious.

"I'm sorry", she said contritely.

"Just kidding, I know you meant no offense."

"You gotta go but you bring Debra by to see me. Maybe we should give you all a house warming party."

"Maybe. Can't think of that right now."

I had been surprised not to have heard from Debra and Gladys all day. They really hadn't cum. If I had their auto pilot capacity I'd probably have cum ten times. When I got on my bike, I felt the phone buzz and start Gladys's text tone. I looked. "Just had one big one and never touched myself. I was just thinking of you on my way to Debra's office." An erotic emoji appeared.

Almost before I could put the phone away, Debra's text chime came. "Gladys walked in and I looked up and came. Wow! Can't wait to see you at 7. Oh, God almighty, I just came again. You and Gladys are just too much." Another erotic image. 'Where did they find this stuff?'

I texted back to both, "Following the rules."

"They both responded, "That's good to hear you'll be well loaded for us."—two erotic emojis.

If I was going to cum spontaneously, I'd do it now. But no such luck.

I rode home and lay down thinking I may take a nap.

Napping though is difficult when the only thing on one's mind makes a guy hard as a rock. My mind kept wondering what kind of clothing Gladys and Debra would wear. Would it be chaste or sexy? It mattered little, it's hard for them not to be sexy. That the whole affair was going to lead to me having intercourse with them both led to highly erotic thoughts. Unlike many men, I was not turned on but thinking of deflowering a young lady. I was turned on by having intercourse with Debra and Gladys the first time.

I must have been really tired because I woke up at 6 with a start. I looked quickly for the time and saw and jumped up to get ready. There really was no hurry as all I needed to do was shower and dress.

So I did and sat down to read one of the essays I needed to use to prepare a lecture. That went all right, but I kept getting distracted thinking about Debra and Gladys which did nothing for the state of my cock which was now imprisoned in the underwear they had bought me. Was I really supposed to wear these things? Were they in to BDSM?

At last it was time to go if I was going to walk and I had decided I should do so. It was about as easy as putting on my motorcycle gear. I grabbed my jacket and the flower arrangement I had bought earlier and took off arriving almost exactly at 7.

I knocked and after a suitable amount of time, both women opened the door. I was flabbergasted. Except for hair and eye color and a slight difference in breast size, they look like twins. Both were dressed in white dresses of translucent material. The only thing keeping me from seeing their parts was that the material hung in folds down their bodies gather at the waste by a 1 and 1/2 inch belt and then the material flowed out into a more or less full mini skirt, emphasis on the mini. The skirts only came down maybe four inches beneath their pussies. What actually covered their breasts was only five inches wide at the waist and was then gathered at the shoulder by a piece of the same material sewn around it.

They turned in unison as if they had choreographed the scene to show me their backs. The front was a halter, their backs were bare to the waist. I could barely see the outline of their asses through the gathered material of their skirt.

Needless to say my painfully constrained cock took a leap and grew harder. I presented them with the flowers, saying, "For my beautiful girl friends."

They received them in glee, both kissed and hugged me enthusiastically, and decided they should pin one on themselves. We went to kitchen. Gladys fished out a few straight pins from the drawer and Debra cut two of the flowers from the bouquet and they pinned them on each other.

They turned to me and Gladys said, "You look quite handsome tonight, Sir. Have you done that just for the damsels you are taking out." They giggled.

"Yes, my dears, it is all for you."

They giggled some more. If I hadn't known better, I'd have thought they were drunk. We had decided we would restrict ourselves to two drinks each at the restaurant. Still we decided on the spot to call Uber for transport. That way nobody would be left out on the 20 to 30 minute ride out. This was a special night after all.

The car arrived 5 minutes later and we got in the back seat. I'm not sure whether it was by design or happenstance, but I ended up in the middle. I do not like sitting in the middle of a back seat. However, this turned out to be to my advantage because I had four hands constantly touching me, massaging my cock, and two mouths wanting to kiss me the whole trip. For some reason, they found the predicament of my cock amusing. I had to warn them that were they to continue messing with it, we would have a mess.

Once we arrived at the restaurant, all eyes of the male valet staff were on us. The women obviously eyed Debra and Gladys with envy. Have I said how hot they looked. I could barely keep my hands in appropriate places and hoped we'd be seated where I asked to be seated.

I spoke to the hostess and told her we had a reservation and she looked at me with some amusement and said, "Yes, sir, Dr Roberts, this way." 'How did she know I was a professor? I'd not told the person who took the reservation. Had she been a student?'

She led us to the table I requested. I had noticed it when I had come for drinks with some friends some time ago and thought it would be a great romantic hideaway. The table was on the far end of the deck. To get to it one had to duck around a tree limb. While it did not provide complete privacy, it gave a modicum of privacy. Enough anyway.

Debra and Gladys were thrilled and showed it by exclaiming and hugging each other and then hugging and kissing me. Immediately, they went to the rail on the west side overlooking the river and with the sunset closing in, the colors were beautiful, the night was warm enough for their dresses and too warm for my sports jacket.

I joined them and put an arm around each of their waists as I stood between but behind them because they were joined at the hip. They are so small, my hands reached their navels. They were not there long. Each took my hand and placed it on her respective breast and then moved the material out of the way so I was holding two bare breasts.

My cock was straining mightily to get out of the underwear so much that it hurt. I said, "Ladies, I have a problem."

"What's that?" asked Debra reaching down to feel my cock. "It seems in great shape."

"It hurts in the under pants you all bought me and as hot and sexy as the two of you are, it'll get no relief even when I ... ."

The waitress interrupted me by ducking under the tree. I turned, Debra and Gladys fixed their dresses and turned and we ordered. Gladys and Debra ordered daiquiris and I ordered a beer. The waitress left and we turned back to our positions.

Gladys asked, "So what do you propose we do?"

"I think I need to go take them off. I'm not a masochist."

Debra innocently asked, "What's a masochist?"

Gladys chimed in, "It's a person who enjoys having pain inflicted on them."

"I don't think I am one either then", replied Debra.

"I know I'm not and I am in pain right now."

"Maybe I can help", said Gladys who turned and unzipped my pants, reached in and liberated my cock. Then she pulled my balls out of the underwear and arranged the 'waist band' under my scrotum. Then she began stroking my cock. Debra reached in and began massaging my balls.

"Does that help, darling?" Debra asked kissing me passionately.

'Were they going to tease me to death?' I thought and then said, "Yes, babes, it does help but I am going to look funny walking around like this."

"Oh, we'll zip you up when need be", replied Gladys with a smirk on her face. She knew exactly what I meant. With my balls suspended as they were and my cock hard as it was, I'd be displaying quite a package. "The question is, does it feel better or not?"

"Yes, it does feel better."

"OK, then, we'll eat dinner like this and then we'll figure out what to do when you go out in public."

It was much better now than it was, but the extra stimulation on my balls and base of my cock did nothing to relieve the pressure on my cock. If I were to cum now, I believe it would shoot across the river.

The waitress came with the drinks and brought them over. Debra took each one and handed them out all the time keeping me invisible to the waitress. The sunset was almost over by now and the deck was growing dark. Our little place had only a little light that shone in from the bar. The lighting on the deck was blocked by the tree.

We drank and made out. The dresses perfect for freely being able to grope breasts and pussies. I discovered neither Gladys nor Debra was wearing panties so playing with pussies was quite easy.

Our waitress returned to take our orders. We had taken time to decide on that and we ordered. I think she sort of figured out that we were not just standing around talking when she entered the area and Gladys had her tongue down my throat and Debra was evidently feeling her up and stroking my cock. She couldn't see real well because of the lack of light, but there was obvious active engagement.

We asked her to bring us another round with our entrees and she said she would. We then had about 20 minutes of uninterrupted sex play. Debra and I began sucking on Gladys's luscious breasts and sort of fought over penetrating her pussy. I gave up and began fingering Debra's feeling something I couldn't figure out. We were too into the sex to ask. Gladys sort of stood look out to see when the waitress was returning as she moaned and thrust against Debra's hand.

For her part, Debra was also thrusting against my hand, trying to get my fingers deeper. She was being successful, but standing was not the best posture for what we were doing. Nevertheless both began to cum almost at the same time. Debra had her mouth occupied with a breast which muffled her moans and screams. Gladys, however, had to bite her hand to keep from screaming out. She quaked so much that Debra and I had difficulty keeping her breasts in our mouths. Once the two came down, we took a break and laughed at what we were doing.

I had not cum and was feeling the need to so I asked, "Mistresses, may your humble servant have an orgasm?"

"Not yet!" they said in near unison. They were not biological twins, well sort of since they are both very female, but they were certainly quickly becoming emotional and mental twins.

I suggested then that we have a seat with me in the chair and them straddling my thighs. That position enabled me to fondle or suck their breasts and/or kiss either one. I began by kissing Debra and fondling one of each of their breasts. I'd flick my finger over the nipple for a while and then just caress the breast for a bit longer then switch breasts as I switched mouths. The woman not kissing with me kissed either my neck or that of the other woman.

We were all very turned on and when they orgasmed almost simultaneously, I was on the verge of a spontaneous orgasm. I wondered if that was their intent. I also wondered if women who lived and made love together began to cum together as they often synched their periods. I'd have to do some research on that.

As they came, they squirmed on my leg and emitted enough fluids to wet my pants legs. I could have cared less. I'd have wet my pants at this point and walked out unabashed I was so turned on. For some odd reason, a thought passed my mind.

Just a bit ago when I was fingering Debra, I noticed something I could not identify. Something in her pussy. I decided to investigate which meant exploring her pussy. I loved feeling inside their pussies so my state of excitement would not diminish. I started trying to penetrate them both. They teased by acting as if they did not want me to do so. Of course, with them straddling my thighs it was not the easiest thing but eventually they permitted my exploration.

I discovered that whatever it was, both of them had it. I could tell it was hard and round, but why would they have a hard round object in their pussies. So I asked.

Debra sort of looked embarrassed and shy about it, Gladys said sort of matter of factly, "It's BenWa Balls. Maggie gave a set to Debra and last night we went to the sex shop and bought me a set with the plan to wear them tonight."

"What do they do?"

"They're sort of a toy but they have a practical purpose also."

"The toy part is that they remind you your pussy is there and something is in it", said Debra. "I've been wearing mine sense this morning. I've been turned on all day. I kept thinking of things I could fuck myself with." She laughed and looked at Gladys.

"I've also worn mine all day. Had I not promised to not masturbate, I would have done so a dozen times. It was all I could do not to rape Debra earlier when we saw each other or before we came here or ..., Oh", she said, "I guess I've been raping her since we left home."

Debra broke in, "The practical part is that if we do exercises with them, several times a week, then we can keep our pussies tight and our pelvic floor strong so we don't start having bladder and uterine problems as we grow older."

"Well, it is certainly sexy to learn you have them in. Can you text me from now on when you are wearing them? I know I'll be turned on by it."

They both smiled big smiles and said, "Absolutely!"

I did not remove my fingers until the waitress returned. I do not know if she noticed what was going on, because Debra and Gladys just stood up and my fingers slid out and their skirts, as short as they were, covered my hand in their pussies.

The waitress set the food on the table and said with a smirk, you guys having a good time. I said, "The best!"

We devoured the food. The time of day and the activities had made us hungry. Once we had finished eating, we ordered dessert which we planned to share. It was a very elegant fudge sundae.

Debra got an idea that Gladys immediately seconded which meant I had nothing to say about it. Debra took a small spoon full of the fudge and having taken my cock out of my pants, dabbed it on the head and then licked it off. Gladys repeated the act. It felt good to have my cock licked, but I knew if they did not get me off, my balls would just get bluer. I have no idea how I avoided a spontaneous orgasm. I was more turned on than I think I had ever been. Of course, I was leaking cum like crazy. Maybe that was the answer.

They didn't get me off saying they wanted it all saved for when I screwed Debra the first time. I thought I may just blow her right off the end when I did cum. That sent odd cartoonish images through my brain.

We finished the dessert which I mostly ate while they were dipping fudge onto my cock and licking it off. I called Uber to pick us up, paid the check and we walked to the front of the restaurant. I hadn't thought about rearranging my cock having sort of gotten accustomed to it. When I got to the front where there was light, Debra looked and then moved to hide my very obvious erection. What she did though was nice as she got in front of me and backed her ass up to it and whispered, "Don't you wish you could put it in me?"

I replied, "I'll be doing so pretty soon. Are you ready?"

"I'm so ready you could bend me over right here and do it. Gladys has plans though."

This time it was Debra in the middle and Gladys and I played with her breasts, her pussy and one of us was kissing her the whole way home occasionally taking a moment to kiss each other. By the time we unlocked the door, there is no way any virgin had ever been more ready than was Debra.