Jack, Dianne and a Super Bowl

Is that a little. . . phallic?

It happened on Super Bowl Sunday. My lady friend, Debbie, and I had been out skiing and had returned in time to shower, prepare a snack and drinks and settle in to watch the Broncos and Packers do battle.

I am not sure whether it was the exercise, the drinks or the warm fire but before long I felt myself dozing off. The next thing I remember the doorbell was ringing and our friends, Jack and Dianne, appeared. Debbie had invited them over to watch the game or at least for Jack to watch the game while the two girls went out for a walk.

Dianne and Debbie used to work together and they have stayed very close. Sometimes it seemed too close for my liking. They share many details of their lives with each other but Deb assured me that she had not ever mentioned my penchant for crossdressing.

Jack and I had never been very close. He didn’t really share my interest in outdoor sports and because of my other private ‘hobby’ I have stayed away from developing any close buddy relationships with guys that would cut into my crossdressing time. Besides, and this may seem strange coming from me, I couldn’t really warm to his slightly effeminate mannerisms. There was never any doubt that, figuratively at least, it was Dianne that wore the pants in that family.

The girls left for their walk; Jack and I settled back in on the couch to watch the game. Several hundred million people know how the game unfolded and will probably remember how the Green Bay Packers took an early lead but the Broncos came back. But it all seemed a sleepy blur to me. I do remember casually mentioning to Jack that the girls were missing a good game.

“They may not be seeing it but I’m not sure they’re missing it” said Jack.

That was a cryptic comment typical of Jack. I assumed he meant that they were enjoying their walk in the forest reserve behind our house and I made no reply but then Jack continued, “If I know Dianne she has her mind if not her lips firmly on Debbie’s lovely breasts.”

“Ha. Right.” I replied sarcastically but slightly excited by the prospect of the two beautiful friends engaged in some sort of lesbian tryst.

“No, really,” Jack insisted, “Dianne and Debbie have a bit of a history. When Debbie’s marriage was breaking up the girls were really close and somehow their friendship became physical. I know Dianne has never given up her attraction for your lady friend.”

“That’s crazy. No way,” I said. By that time I had completely lost interest in the game and as Jack went on to give a few more confirming details about the relationship. I knew he was telling the truth and I found myself becoming sexually aroused by the images of the two girls together in bed.

At that point Jack went to the kitchen and returned with a new round of drinks. He settled in a little closer to me and noticing my arousal he said, “I see the thought of the girls doing it isn’t so objectionable to you,” and he casually patted my erection.

“No it’s not,” I admitted, “and your hand feels pretty good, too.” I couldn’t believe I had said that but I was too aroused and perhaps too much under the influence of my drinks to act rationally. I hadn’t even thought of the consequences of what would happen if Jack were to want to go further and take out my penis. He would then discover what only Debbie and I knew — I have a particular preference for women’s underwear.

It didn’t take long to find out what would happen as Jack took my comments as an invitation to further exploration. As I sat there on the couch he undid my zipper and started to pull out my near erect penis.

“Umm, nice panties,” was all he said as he pulled my penis out from under my black Calvin Klein 100% cotton bikini briefs. For a brief time he stroked my penis as I sat back trying to take in what was happening, enjoying the feeling but bothered by thoughts of the inevitable fallout. “I always suspected that Jack might be gay. What would happen if the girls came back? Will Jack tell anyone about my panties? Should I reciprocate his hand job? I want to.”

It wasn’t long before Jack leaned over to put his mouth over my penis. Wow! That felt good. As he took me ever deeper in his mouth I put my hand on his back and that’s when I got my next surprise.

By now it was half time in San Diego and off in the distance I was aware that a whole bunch of people were singing the praise of Motown, but my mind was now taking in the fact that there was a man with his face in my lap and my hand on his back was discovering that he was wearing a bra. Even through a shirt and heavy sweater there was no mistaking the outlines of that most delightful undergarment.

“Is that what it feels like?” I asked.

“Umm” was the only reply as he continued to suck on my penis.

“Are you into crossdressing?” I asked Jack.

He sat right up, got a sweet little smirk on his face and said, “what was your first clue?” He then proceeded to take off his outer clothes. Under his shirt and sweater Jack was wearing a black lace demi bra with a small cup that neatly pushed up his chest tissue into pert little breasts more like a 13 year old girl’s than the chest of a 40 year old man. Under his pants and socks he revealed matching lace panties and garter belt attached to black stockings.

I couldn’t help notice that despite his small panties there was no sign of the penis and testicles I knew must be tucked between his legs.

The girls had been gone for two hours and I was afraid they’d return any minute but Jack assured me they’d be gone until they thought the game would be over. So as the teams returned to the field I led Jack upstairs to my ‘private room’ where I keep my ‘Linda stuff’. We each picked out dresses, high heel shoes and wigs and started to do our make up at the bathroom sink. My dress was black with a white floral print and a loose flowing skirt that came to just above the knee. Jack chose my green spandex mini dress with the low neckline.

As we transformed we talked about our experiences. Jack told me that Dianne had discovered early in their dating that he enjoyed the feminine role in a relationship and that was fine with her. She didn’t consider herself a lesbian but apparently that didn’t stop her from occasionally enjoying the carnal company of other women or of her husband in drag. Debbie, on the other hand, had never wanted to be in bed with Linda but according to Jack she and his wife have an ongoing occasional sexual relationship. That didn’t surprise or shock me. I shared with Jack how much I enjoyed my trips to California and the people I meet there. I admitted that sometimes I would make love with other crossdressers and men I would meet there.

As we finished our makeup and put on our wigs I glanced at Jack and a light went on in my mind. “Are you the Jacqueline from the gender group?” I asked. “Yes” was the sly reply. I had met Jacqueline a couple of times at group meetings and had never made the connection to Jack.

“Well, I’m known as Linda; we’ve met before.”

“It’s a small world,” said Jacqueline as she slipped her arms around me. “Of course I remember you and I never would have made the connection in that context.”

“Lets get drinks,” I said, deciding that if the girls were to return they would have to deal with what they found. After dressing and letting this pretty genie out of the bottle I had no intention of jamming her back in.

Back in the living room the Super Bowl game was drawing to its exciting conclusion so Jack and I sat close to each other, sipping a ladylike glass of white

wine, each with a hand on the other’s leg and we watched as Mr. Elway and his teammates drew closer to their previously elusive prize.

As the Packers hopes for a repeat victory came apart, we heard the girls coming in by the side door. “Hello” they called then as they came into the room, “What’s this?” exclaimed Debbie. She explained later that she thought Jack and I might have had two cute friends drop by. “Who are you and what have you done to our husbands?” joked Dianne for she seemed to know right away what was going on.

In fact Dianne immediately moved in and sat between us and placed one of her hands in each lap. “Come on, Deb,” she said, “I know I was good but you must have something left. Let’s see what these girls have.” She lifted Jacqueline’s, or Jack’s, skirt, pulled out his penis and proceeded to stroke it. Debbie was quick to catch on and mimic her friend’s actions although in wanting to impress Jack with my feminine figure I had put on a high waist girdle which made Debbie’s job of getting at my private parts considerably more difficult than Dianne’s move on Jack.

Imagine the scene: two crossdressed males sitting back on a couch as their female partners knelt in front of them, performing oral sex while on television the Denver Broncos and their fans celebrated their long awaited victory. Soon the girls changed partners and then I saw Dianne move her hand into Debbie’s loosened jeans and Debbie placed one of her hands under her friends blouse and on her sweet breasts. Things were really getting hot.

At that point I heard the phone ring and Debbie disappeared to answer it. Then before I knew it she was back but our friends were gone and so was my dress.

“It’s about time you woke up,” said Debbie, “the game is just beginning. That was Dianne on the phone; she wants me to

go for a walk with her. Jack will be bringing her over and then watching the game with you.”

It had all been a dream. But was the dream a window on the future?

Tags: crossdressing, featured, fiction

Category: Transgender Fun & Entertainment