Big Cock Graduate

Cathy grabbed a bottle of wine and she congratulated me on job well done. Nancy and Cathy both coached me on my confidence and what I might do when I saw her tomorrow. This helped keep Nancy's mind off of Andrew.

I would drive down and pick Tracy up tomorrow afternoon. We were going to go to dinner and then planned to see a free concert in a local park.

I arrived at her place which was beautiful old brick house from a bygone era with a big drive to the main house. I believe her apartment was a converted horse stable from generations ago. They had put in large windows all around the apartment.

On my way up from the road, I met Debbie, who was the woman Tracy worked for. She was a stunning classy lady, about five foot ten inches tall, long blonde hair in a ponytail, and a tight summer dress that showed off her toned body. She was still quite young and had the looks of a young Nicole Kidman. I introduced myself to her, and let her know I that I was there to pick up Tracy for dinner.

Debbie was very thankful as she knew Tracy hadn't met many other people her age and she was thankful to have a professional working to help her with their toddler who was currently sleeping. Debbie made a bit of small talk about where I had come from and seemed impressed with the engineering. She said, "So you are not only good looking, but you are smart. I hope you have a great evening with Tracy."

I found out that Debbie worked in marketing and was recently separated. I complimented her on her lovely home which she said she had acquired through her family who had lived in the city for generations.

I rang the doorbell and Tracy came to the door. She was stunning. Tracy had coppery red hair halfway down her back. She had a heart-shaped face, an alabaster complexion, green eyes, and full red lips. She had a tight body with a flat stomach, and perky full breasts. Tracy was about five foot three, and was a lot shorter than Linda.

I had always been worried about a big height difference and how that might make it harder to communicate.

Tracy was wearing a tiny black dress with heels. I complimented her on her beautiful hair which was apparently from an Irish heritage.

Tracy returned the compliment remarking on my height and blonde hair. She said that she noted my height in my profile and had donned heels that would help.

We talked briefly and then headed out to dinner saying goodnight to Debbie on the way out.

Over dinner, I got to know Tracy, her love of family from down east, where she had two sisters that she was very close to. She mentioned that her younger sister had just graduated from high school and was coming to my town to go to college. She talked about her working for Debbie, who she said was a great lady and treated her very well. She added that she thought Debbie was lonely after her separation.

I talked a bit about work and volleyball which I had played for our varsity team. Her eyes sparkled when she talked and the evening was going very well.

After dinner, we walked to the park that was hosting the concert. It was crowded and we were getting jostled around which meant that Tracy was bumping into me which included her 'accidentally' grazing my crotch. That sent a bolt of electricity through me which I am sure she noticed.

When we got closer to the concert, it became impossible for Tracy to see anything due to her height. To help her out, I hoisted her up to my height for a better view. She loved it and I was able to feel how toned she was.

We left the concert after about an hour, and we headed back to her place. It had been a great evening and I was hoping that it wouldn't end yet. During the walk back to the car, I held her hand through the crowd.

Back at her place, she invited me in for a coffee. I, of course, agreed. She had a sectional 'L' shaped sofa, and I took a seat while she ran the coffee machine. We made some more small talk during which I went in for a kiss. She seemed fine with this, but didn't respond back with vigor.

My insecurity with women got the best of me and I backed off from going further. We agreed to talk during the week and to possibly meet the following Saturday for another date. On my way out, she gave me a warm kiss and a hug. I was willing to wait and see where this would lead, as she was such a nice person paired with a spectacular body.

The week went by and we talked and texted a few times. Tracy was engaging in her conversation and was very keen for our next date.

During the week, I recounted the date with Cathy and Nancy. They encouraged me to go further and said that from what they had heard, Tracy liked me.

Cathy said, "Doug, you need to be more forward on your next date. If Tracy invited you in, she was open to more than a kiss. I know that is what I would be saying if I were her. Don't force her in any way, but be more forward and take command."

The following weekend, I drove down to her place. If I was going to get anywhere, I didn't want to run the gauntlet past Cathy and Nancy.

As I pulled up, Debbie was just leaving. She rolled down her window and said that she was pleased to see me again. I was dressed in pants and black button-down shirt. Debbie added how sharp I looked and hoped that we would have a good time.

Tracy and I went to comedy club that night and made a critical error in choosing our seats. We sat in the front row which encouraged the various comedians to go for jokes at our expense. They commented on Tracy's good looks and on my height. One even commented on the size of my size fourteen feet and speculated on other parts of my anatomy based on this.

I tried to fend them off, but you never want to get into an argument with someone who has a microphone.

We did have some good laughs and tried to take the ribbing in stride, but eventually headed back to her place.

Tracy invited me in again and we retired to the couch. I went in for a few kisses and got a bit more of a response. While kissing I ran my hands up he sides and grazed those wonderful breasts. She seemed more receptive tonight and I thought of my coaching from Cathy and Nancy to be bold and confident.

Between kisses, Tracy mentioned the comedian's comment on my shoe size and comparison he made. I suggested that she would be able to make her own judgement tonight if she was into this. She smiled and just nodded.

I didn't need any more encouragement and started to softly touch her body all over. When I touched her breasts, they were firm. I then moved to start unzipping her dress on the back to be able to get a closer look.

I was fumbling with the zipper and she ended up standing up and just dropping her dress, bra, and panties. She was magnificent with same creamy white skin with a few freckles, pink puffy nipples, and red pubic hair.

I ran my hands up and down and kissed her bare belly which was at eye level from my seated position on the couch. I then gently lifted one of her legs and leaned in to give her pussy a quick lick.

Tracy shuddered, grabbed my hand, and took me to her bedroom where she left the lights on.

I quickly stripped and joined her on the bed. I continued to explore with my hands by lightly touching her breasts and then stroking her inner thighs. Slowly, I moved her legs apart and gently kissed her inner thighs before engaging her pussy with my mouth.

Tracy moaned a bit, but didn't move around very much. I continued to lick her vagina and slowly probed her with a finger. I eventually felt the shiver of an orgasm from her. I then moved up to be face to face with her.

Tracy tentatively reached out and grasped my cock. I encouraged her to do more and she slowly started to stroke me and eventually moved down to suck it. Before she put her red lips to my cock, she said, "That comedian underestimated your size. This is the largest cock I have ever seen!"

I would say that Tracy was clearly inexperienced at giving head. She bobbed a bit on my glans, but did not match her hand strokes of my member with her mouth. She eventually stopped, came back up and spread her legs, obviously inviting me in.

I entered her slowly, as I knew that my size might be a challenge. I did my best to restrain myself from getting too aggressive and eventually achieved orgasm inside her. Afterwards, I laid there thinking that this was very average sex compared to Linda, my first girlfriend.

Tracy was clearly eager to try, but had been shy throughout our evening. It was possible that she was inexperienced and needed guidance. As an engineer who is always looking to solve a problem, I started thinking of how I could help guide her. I drifted off dreaming of ways to spice this up.

In the morning, I woke up and saw that Tracy had a big picture window that was only a few feet from her bed that looked over a small row of hedges at windowsill height and then the yard. Upon awaking, we started stroking each other.

We went and had a shower together where we got a bit friskier.

After drying off Tracy, I proceeded to push her to the bed where licked her pussy again. In addition to inserting a finger into her, I played with her rosebud, and even put in a finger in her ass up the first knuckle. She squirmed a bit and let out a soft moan, but didn't add any other indication if this was something she liked, or did not.

I moved up and she proceeded to spread her legs again for missionary. I, of course, complied; but did not go as slowly as I had the night before. She enjoyed it when I was bucking hard at the end and her face contorted with an orgasm.

I asked her outright what got her excited and she said that she wanted to lose all control and wanted a man who knew what he wanted. Nancy and Cathy were right, I had to be more assertive.

On leaving the apartment, I walked past the picture window in front of her bedroom and noticed a pair of footprints in the dirt near the bushes in front of the window. I suspected that we may have had an audience last night.

On the way down the driveway, I saw Debbie once again, this time retrieving the Sunday newspaper. I greeted her warmly. She seemed thrilled to see that I had stayed the night and that Tracy and I were getting on so well. I did note that her foot size seemed to be like the prints in front of the window and I did catch her giving my groin a good look.

I suspected that Debbie was our audience last night, and that she might not be getting satisfaction after her separation. I had to depart, but gave her a quick hug. I could feel the swell of her breasts during our hug and she may have felt the partial erection I had.

After the embrace, Debbie seemed a bit flushed and expressed her hope that I would return.

Chapter 3: Tracy and Debbie

Tracy and I talked and texted through the week.

Verbally, I recounted our evening and asked what she liked and didn't like. Tracy was evasive and just said she was happy to do whatever I wanted. By mid week, I started to insert some ideas for the weekend into my texts suggesting that she would spend some more time stroking and sucking me at the same time.

Tracy responded with a YES.

My plan for the next Saturday was to make her dinner and then just watch a movie on TV. I arrived at her place and started to set up to make sea bass with mango chutney. Unfortunately, Tracy didn't have a pan large enough for the fish.

We both went over to the main house to see if we could borrow one.

Debbie was there alone with her toddler and, of course, had a large pan. She asked what we were going to do, and I mentioned the movie. She said she was all alone and we would be welcome to watch it with her on her state-of-the-art home theatre system and that if we didn't mind, she could join us after putting her child to bed. "All my time goes into work and looking after my child. It would be great to spend some time with adults doing something as simple as watching a movie," she added.

At first, I thought this would put a cramp in our evening, and then thought, that this could be interesting based on my observations from the past weekend.

I finished the cooking with Tracy, and we had a wonderful meal.

Over dinner, Tracy said that she thought Debbie was being a bit too friendly by horning in on our date.

I suggested that Debbie was lonely and that she may be trying to live vicariously through her. I told Tracy of my voyeur theory from last weekend. I suggested that if Debbie was into watching, we could give her a bit of a show.

Tracy didn't say much, so I then and asked her if she would be open to this. She just blushed a bit and nodded.

We headed over to Debbie's wearing loose lounge clothing. She was just putting her child to bed when we arrived, but said we should make ourselves comfortable.

I opened the second bottle of wine I had brought, poured three glasses and we then went to their theatre room. Tracy and I sat on the main couch and had a blanket over our legs. Debbie joined us, thanked us for the wine and sat in the chair which partially faced the screen and partially faced us. Debbie joked about what an attractive couple we were, and how happy to see the chemistry we had going. Debbie had changed into a big robe, as she mentioned that her clothes had been dirtied.

I started the show and we settled in. During a loud part of the show, I whispered in Tracy's ear that now would be the time to start the stroking. I could feel a bit of hesitancy on her part, but she nodded and slowly moved her hand under the blanket and liberated my semi-hard cock.

I looked over and saw that Debbie had noticed Tracy's movement. The size of my erection made it hard to hide what were doing. Debbie had spread her legs a bit in the chair and had a hand resting in the crotch of her robe.

All of this was getting me very hard, and I was now at my full nine inches with the head of my cock starting to show at the top of the blanket.

Debbie tried not to look, but then took a glance, and let out a little moan. I saw her spread her legs a bit more, and her hand seemed to be burrowing into her robe.

Seeing that she was enjoying this, I decided to take this to the next level. I had my arm around Tracy and gently started pushing her head to my aching cock. She slowly complied while blushing hard.

I looked over to Debbie and saw that she had now given up all pretense and was openly staring at us, as Tracy opened her mouth and took the head of my cock in. I let the blanket fall away to offer Debbie an unobstructed view as Tracy started to suck me.

Tracy would only lightly bob on the tip of my cock and still didn't have the hang of stroking me in time to the movement of her mouth.

Debbie, on the other hand, had swivelled her chair around and now had her housecoat completely open showing us her toned body. Debbie was leaner than Tracy and had smaller pear-shaped breasts. She had a tight body and was now exposing her shaved pussy to us in the chair. She shifted and squirmed down in the oversized chair and was now openly fingering her pussy with one hand. With her other hand, she had put it under her and was then inserting her index finger into her asshole. What a kinky woman.

Even though Tracy's cock sucking was not great, the excitement of having Debbie watch and masturbate in front of us, had me on the verge.

Debbie came first with little animal sounds and she had two fingers in her pussy from her right hand and two in her ass from her left.

I felt my balls boiling and grunted as I shot cum into Tracy's mouth.

Tracy was caught off guard and immediately pulled her face away. Some cum dribbled from her lower lip and she had one line across her cheek. The rest was oozing out of my still semi-hard cock onto my lower abdomen.

Debbie was the first to speak. She said in a husky authoritative voice, "Tracy, you still have a mess to clean up."

Tracy looked at her with a look of confusion.

Debbie shrugged and stood up and said, "I guess I will just have to show you."

She then came over to us and kneeled in front of me she then took my still semi-hard cock and licked the semen on the tip of my cock while pumping the shaft to get all that she could. She swallowed that and then pointed to the small pool of cum on my stomach and said to Tracy, "Finish your dessert."

Tracy was still not comprehending, so Debbie grabbed Tracy's head in both hands, licked the stream of cum off her face and said, "Open your mouth!"

Tracy's jaw dropped and Debbie took that opportunity to spit the cum into Tracy's mouth. Debbie held Tracy by her hair and guided her face to the pool of cum on my lower belly.

Tracy finally got the message and started licking up the goo.

This had me revved right back up. I was thinking of how to proceed... I reached out to Debbie and said, "That was so hot."

I looked over to Tracy and asked if she was okay at being directed. She just had a big smile on her face and said, "That was awesome."

I responded, "There might be much more."

Debbie had moved from between my legs and was now sitting next to me with one hand slowly stroking my cock. She then casually said, "What comes next?"

I said, "I assumed we would head to your bedroom where there would be a lot more sucking and fucking."

"I am up for anything," Debbie nodded and then asked, "Have either of you two had a threesome before?"

Tracy and I shook our heads in unison.

Debbie said, "We are going to have a lot of fun and I want you to understand what could happen and understand what you are okay with."

I said that I was up for anything with the two of them tonight, and gave Tracy a little squeeze of encouragement.

Tracy was a bit hesitant and asked how things might work between her and Debbie.

Debbie said, "I believe that we all need to be willing participants and that may involve things that are new for us." Debbie added that she wasn't a lesbian, but that she may do things tonight and later that might make us think so.

Tracy seemed unsure about that and so Debbie expanded on this idea by saying, "During a threesome with two women and a man, there would be times when two of us would have to focus on the pleasure of the third person and this would mean some woman on woman contact." She went on, saying that Tracy shouldn't knock it before she tried it and that she would take the lead. "The bonus in doing this, is that it is almost every man's dream to have a threesome with two women. You would give and get more pleasure while fulfilling Doug's fantasy."

Making the act about pleasing me, pushed Tracy over the edge and she simply said, "I am in." I kissed Tracy passionately and then turned and gave Debbie a quick kiss.

Debbie had a big smile on her face and said, "Oh my god, I can't believe that this is happening. I am so looking forward to getting slammed by this world class fuck stick. Tracy you will not regret this, and I will help see that you cum like a freight train tonight."

We started to head to Debbie's bedroom. As we were getting up, I asked Debbie if she had watched us the other evening and she readily admitted her voyeurism. She was fascinated with the size of my cock and wanted to experience it firsthand. She said that when I had seen her last weekend on the driveway, that she had actually been out there multiple times just trying to get the opportunity to interact.

I asked her what other surprises she had. She said that by going to her bedroom, we would be fully equipped with toys.

When we got there, I said that since we had both gotten off, that it would be Tracy's turn to get our attention.

I lifted Tracy's top and Debbie moved to stroke her breasts as I dropped her pants. I then slowly pushed her to the bed and said she should get on all fours in the middle of the bed.

We both started rubbing her all over. Debbie was reaching around and pinching Tracy's nipples as I dropped behind Tracy and started to lick her up and down her slit and gave her rosebud some attention.